Flavonoides Recommendations

Page 1 of 53
Nomenclature of Flavonoids
(IUPAC Provisional Recommendations)*
Amlia P. Rauter1, Bernardo J. Herold2, Derek Horton3, Gerard Moss4, Ida Schomburg5, KarlHeinz Hellwich6, Marcus Ennis7
4
5
6
1
Universidade de Lisboa, Faculdade de Cincias, Departamento de Qumica e Bioqumica/Centro de

Qumica e Bioqumica, Ed. C8, Piso 5, Campo Grande, 1749-016 Lisboa, Portugal; 2Universidade de
Lisboa, Instituto Superior Tcnico, Av. Rovisco Pais, 1041-001 Lisboa, Portugal; 3American University,
Department of Chemistry, Washington, D.C. 4400 Massachusetts Avenue NW, Washington, DC 20016, USA;
4
School of Biological and Chemical Sciences, Queen Mary, University of London, Mile End Road, London
E1 4NS, UK; 5Technische Universitt Braunschweig, Institut fr Biochemie, Biotechnologie und
Bioinformatik, Langer Kamp 19B, 38106 Braunschweig, Germany; 6Postfach 10 07 31, 63007 Offenbach,
Germany;7European Bioinformatics Institute, Wellcome Trust Genome Campus, Hinxton, Cambridge CB10
1SD, UK
ee
7
8
9
10
11
12
13
14
15
rP
Fo
16
Abstract: Flavonoid structures, found in nature or obtained by synthesis, have become more and
more complex, and a guide for aglycone names is provided here to permit the construction of the
names for their polyglycosylated species with clarity and conciseness. A joint working party of
IUPAC/IUBMB members has prepared these recommendations, which establish rules for the
general nomenclature of flavonoids, providing examples of acceptable trivial names, and names
derived from trivial names, together with semi-systematic and fully systematic names that follow
the published IUPAC recommendations.
ie
ev
17
18
19
20
21
22
23
rR
24
25
CONTENTS
26
Flv-0 Introduction
27
Flv-1 Flavonoids Definitions and conventions
28
Flv-1.1 Flavonoid classes with a C6-C3-C6 carbon framework
29
Flv-1.1.1 Flavonoids
30
Flv-1.1.1.1 Flavans
31
Flv-1.1.1.2 Flavones and 3-hydroxyflavones (flavonols)
32
Flv-1.1.1.3 Anthocyanidins/anthocyanins (anthocyanidin 3-glycosides)
33
Flv-1.1.2 Isoflavonoids
34
Flv-1.1.2.1 Isoflavans
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
1
P.O. 13757, Research Triangle Park, NC (919) 485-8700
4
4
4
IUPAC
35
Flv-1.1.2.2 Isoflavones
36
Flv-1.1.3 Neoflavonoids
37
Flv-1.1.3.1 Neoflavans
38
Flv-1.1.3.2 Neoflavones
39
Flv-1.1.4 Chalcones and dihydrochalcones
40
Flv-1.1.5 Aurones
41
Flv-1.1.6 Pterocarpans and their 3,4-didehydro derivatives (coumestans)
42
Flv-1.2 Rotenoids
43
Flv-1.3 Flavonolignans
44
Flv-1.4 Biflavonoids and other flavonoid oligomers
45
Flv-2 Guide to the construction of semi-systematic names
46
Flv-2.1 Flavans, isoflavans, neoflavans and compounds derived from them
47
Flv-2.1.1 Flavans
10
48
Flv-2.1.1.1 Flavanaglycons
49
Flv-2.1.1.2 Flavan glycosides
50
Flv-2.1.1.3 Flavanones
51
Flv-2.1.2 Isoflavans
52
Flv-2.1.3 Neoflavans
53
Flv-2.2 Flavones, isoflavones, neoflavones and compounds derived from them
54
Flv-2.2.1 Flavones
55
Flv-2.2.1.1 Flavone aglycons
56
Flv-2.2.1.2 Flavone glycosides
57
Flv-2.2.1.3 C-Glycosyl substituted flavones
58
Flv-2.2.1.4 Flavonols and flavonol glycosides
25
59
Flv-2.2.2 Isoflavones and isoflavone glycosides
26
60
Flv-2.2.2.1 Isoflavone aglycons
27
61
Flv-2.2.2.2 Isoflavone glycosides
28
62
Flv-2.2.3 Neoflavones and neoflavone glycosides
28
rR
ee
rP
Fo
11
11
ev
11
14
ie
15
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 2 of 53
2
16
17
17
19
22
Page 3 of 53
63
Flv-2.2.3.1 Neoflavone aglycons
28
64
Flv-2.2.3.2 Neoflavone glycosides
29
65
Flv-2.3 Chalcones and dihydrochalcones
30
66
Flv-2.4 Aurones
32
67
Flv-2.4.1 Aurone aglycons
32
68
Flv-2.4.2 Aurone glycosides
34
69
Flv-2.5 Anthocyanidins and anthocyanidin 3-glycosides (anthocyanins)
34
70
Flv-2.5.1 Anthocyanidins
34
71
Flv-2.5.2 Anthocyanins
35
72
Flv-2.6 Flavonoids containing additional fused/spiro rings in their structures
38
73
Flv-2.6.1 Flavones
38
74
Flv-2.6.2 Chalcones
75
Flv-2.6.3 Aurones
76
Flv-2.6.4 Anthocyanidins/Anthocyanins
40
77
Flv-2.6.5 Pterocarpans
42
78
Flv-2.6.6 Rotenoids
79
80
81
MEMBERSHIP OF SPONSORING BODIES
82
REFERENCES
ee
rP
Fo
39
39
ev
rR
43
46
ie
47
52
On
83
84
85
86
*Sponsoring bodies: IUPAC Division(VIII) of Chemical Nomenclature and Structure

Representation (IUPAC project # 2009-018-2-800) and IUPAC-IUBMB Joint Commission on
Biochemical Nomenclature
87
88
89
52
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
Corresponding author: Amlia P. Rauter, Universidade de Lisboa, Faculdade de Cincias,

Departamento de Qumica e Bioqumica/Centro de Qumica e Bioqumica, Ed. C8, Piso 5, Campo Grande,
1749-016 Lisboa, Portugal. E-mail:aprauter@fc.ul.pt
90
91
3
IUPAC
92
93
Flv-0 Introduction
94
95
96
97
98
99
100
101
102
103
Flavonoids, including the parent cyclic structures and their O and Cglycosylated derivatives, are
natural or synthetic compounds that are structurally diverse, and many exhibit biological activity [15]. They are quoted in the literature by researchers in diverse specialized areas, including natural
product chemistry, organic synthesis, medicinal and food chemistry, biology, and biochemistry.
Different workers have used a variety of alternative names and naming systems for such
compounds, and trivial names are commonly used to simplify complex names. Semi-systematic
names derived from parent structures are very useful for naming flavonoids, and have been widely
used, but they often lead to misunderstandings. There is an urgent need to avoid ambiguity in the
naming of flavonoids by clarifying acceptable usage and limiting the variety of options to a
reasonable extent.
104
105
106
107
108
109
110
111
These recommendations establish rules for the general nomenclature of flavonoids, providing
examples of acceptable trivial names, and names derived from trivial names, together with semisystematic and fully systematic names that follow the published IUPAC recommendations [6-8].
Class names for flavonoids, their parent structures, and the order of citation of primed or unprimed
locants are revisited and clarified. Names of O- and C-glycosylated derivatives follow established
carbohydrate nomenclature [9]. Semi-systematic names are based on the parent structures or their
functional parents. These are presented and illustrative examples are provided to avoid ambiguous
interpretations.
ev
rR
ee
112
rP
Fo
113
Flv-1 Flavonoids Definition and conventions
114
115
116
117
118
119
The term flavonoid is commonly used to include not only natural products, but also synthetic
compounds related to them. The structural feature of this family of compounds is based on
derivatives of a phenyl-substituted 1-phenylpropane possessing a C15 skeleton, except for the
rotenoids, which have a C16 skeleton but are also phenyl-substituted 1-phenylpropane derivatives,
and that of flavonolignans, whose structure is based on flavonoids condensed with C6-C3 lignan
precursors.
120
The following carbon frameworks characterize the various flavonoid classes:
ie
121
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 4 of 53
122
Flv-1.1 Flavonoid classes with a C6-C3-C6 carbon framework
123
124
125
126
127
128
129
130
These are classes of compounds having a C6-C3-C6 carbon framework which contains a 1benzopyran (chromene) ring system, in which the aromatic ring is defined as ring A and the pyran is
ring C, along with a benzenoid aromatic substituent on the pyran ring defined as ring B. Depending
on the position of the linkage of ring B to the 1-benzopyran (chromene) moiety, three different
classes can be assigned: flavonoids (Flv-1.1.1), isoflavonoids (Flv-1.1.2) and neoflavonoids (Flv1.1.3). The other flavonoid classes that have a structure with a C6-C3-C6 carbon framework are the
chalcones (Flv-1.1.4), the aurones (Flv-1.1.5) and the pterocarpans and their 3,4-didehydro
derivatives (coumestans) (Flv-1.1.6).
4
Page 5 of 53
131
132
Flv-1.1.1 Flavonoids
133
The flavonoids (2-aryl-1-benzopyrans) are compounds with a skeleton of type 1.
134
135
136
137
138
139
rP
Fo
The oxidation state of ring C and its derivatization with hydroxy groups is used to classify
flavonoids into different categories, such as:
140
ee
141
Flv-1.1.1.1 Flavans
142
143
144
145
146
147
Flavans include compounds derived from 1, as well as flavan-3-ols (compounds derived from 2)
and flavan-4-ones (compounds derived from 4), which are generically designated in the literature as
flavanols and flavanones, respectively. Compounds derived from 3 are flavan-3,4-diols, designated
leukoanthocyanidins because their structure can be considered as being derived from that of an
anthocyanidin (see Flv-1.1.1.3), specifically a 3,4-dihydroxy-1,2,3,4-tetrahydroanthocyanidin,
which renders such compounds colourless.
ie
ev
rR
148
w
On
149
150
151
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
152
Flv-1.1.1.2 Flavones and 3-hydroxyflavones (flavonols)
153
154
155
Flavones and 3-hydroxyflavones (flavonols) are compounds derived from 5 and 6, respectively,
which possess a 2-phenyl-1-benzopyran-4-one (2-phenylchromen-4-one) skeleton. The term
flavonol is used as a class name for compounds derived from 6.
156
157
5
IUPAC
158
159
160
161
Flv-1.1.1.3 Anthocyanidins/anthocyanins (anthocyanidin 3-glycosides)
162
163
164
165
Anthocyanidins are compounds derived from 7, which contains a flavylium ion (2-phenyl-1benzopyranylium or 2-phenylchromenylium) as a core structure. Anthocyanidins display colours
from red to purple and, together with their glycosides, the anthocyanins, represent a large group of
plant pigments.
rP
Fo
166
ee
167
168
169
ev
rR
170
Flv-1.1.2 Isoflavonoids
171
The isoflavonoids (3-aryl-1-benzopyrans) are compounds derived from 8.
ie
172
w
On
173
174
175
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 6 of 53
176
Flv-1.1.2.1 Isoflavans
177
Isoflavans are compounds which have the skeleton 8. They may be substituted.
178
179
Flv-1.1.2.2 Isoflavones
180
181
Isoflavones are compounds with skeleton 9, the 2,3-didehydro structure 8 with a carbonyl group at
position 4. They may be substituted.
6
Page 7 of 53
182
183
184
185
Flv-1.1.3 Neoflavonoids
186
The neoflavonoids (4-aryl-1-benzopyrans) are compounds with parent structure 10.
187
188
189
10
190
rR
ee
rP
Fo
191
Flv-1.1.3.1 Neoflavans
192
Neoflavans are compounds with skeleton 10. They may be substituted.
193
ev
194
Flv-1.1.3.2 Neoflavones
195
Neoflavones are compounds with skeleton 11. They may be substituted.
ie
196
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
197
198
11
199
200
Flv-1.1.4 Chalcones and dihydrochalcones
201
202
203
204
Chalcones are compounds derived from (2E)-1,3-diphenylprop-2-en-1-one (chalcone, compound

12). They are early intermediates in the biosynthesis of flavonoids, in which the pyran ring C has
not yet been formed, and are therefore biogenetically and structurally related to them.
Dihydrochalcones are compounds derived from 1,3- diphenylpropan-1-one (compound 13).
7
IUPAC
205
206
12
13
207
208
Flv-1.1.5 Aurones
209
210
Aurones are compounds derived from 14, which is based on (2Z)-2-(arylmethylidene)-1benzofuran-3(2H)-one.
211
212
14
214
rR
213
ee
rP
Fo
215
Flv.1.1.6 Pterocarpans and their 3,4-didehydro derivatives (coumestans)
216
217
Pterocarpans are compounds derived from 15 and from their 3,4-didehydro derivatives 16
(coumestans). They may be substituted.
ie
ev
218
w
On
219
220
15
16
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 8 of 53
221
222
Flv-1.2 Rotenoids
223
224
Rotenoids comprise rotenanes which are compounds with skeleton 17 and rotenones with skeleton
18. They may be substituted.
225
8
Page 9 of 53
226
227
17
18
228
229
230
231
Flavonolignans have structures based on flavonoids condensed with C6-C3 lignan precursors (see
Flv-2.7).
232
rP
Fo
233
234
235
Biflavonoid and other flavonoid oligomers, which occur widely in nature, are exemplified and
named in Section Flv-2.8.
ee
236
237
Flv-2 Guide to the construction of semi-systematic names
238
239
This section illustrates the construction of semi-systematic names and examples are given, with
trivial names, if known, and the systematic names are added.
240
241
Primed locants are placed immediately after the corresponding unprimed locants in a set arranged in
ascending order (R-0.2.4.2 in [6]).
ie
ev
rR
242
243
Flv-2.1 Flavans, isoflavans, neoflavans and compounds derived from them
244
245
246
247
Names of flavans, isoflavans and neoflavans can be derived from the name of the respective parent
hydride (Figure 1). The presence of a characteristic group is denoted by a prefix or by a suffix
attached to the parent name. The suffix is used for the principal characteristic group(s) according to
the priority order given in R.4.1 [6].
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
248
249
250
251
10
Figure 1. Parent hydrides of flavans (1), isoflavans (8) and neoflavans (10).
252
9
IUPAC
253
Flv-2.1.1 Flavans
254
Flv-2.1.1.1 Flavan aglycons
255
Example 1:
256
257
258
rP
Fo
259
Semi-systematic name
260
flavan
261
ee
262
Systematic names
263
2phenyl-3,4-dihydro-2H-1-benzopyran
264
2-phenyl-3,4-dihydro-2H-chromene
265
266
Flv-2.1.1.2 Flavan glycosides
267
Example 2:
ie
ev
rR
268
269
270
(a)
(b)
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 10 of 53
271
272
(c)
273
274
Note: Saccharide moiety shown in Mills depiction (a), in a conformational form (b) and in abbreviated form [9] (c).
10
Page 11 of 53
275
276
277
(2S)-2,7-bis(-D-glucopyranosyloxy)-8-(2-hydroxyethyl)-4-methoxyflavan-5-ol
278
279
Systematic names
280
281
(2S)-2- [2,7-bis(-D-glucopyranosyloxy)-4-methoxyphenyl]-8-(2-hydroxyethyl)-3,4-dihydro-2H-1benzopyran-5-ol
282
283
(2S)-2-[2,7-bis(-D-glucopyranosyloxy)-4-methoxyphenyl]-8-(2-hydroxyethyl)-3,4-dihydro-2Hchromen-5-ol
284
285
Example 3:
287
288
ev
rR
ee
286
rP
Fo
289
Semi-systematic names
290
(2S)-7-(-D-glucopyranosyloxy)-4-methoxy-8-(3-methylbut-2-en-1-yl)flavan-2-ol
291
(2S)-2-hydroxy-4-methoxy-8-(3-methylbut-2-en-1-yl)flavan-7-yl -D-glucopyranoside
ie
292
On
293
Systematic names
294
295
(2S)-2-(2-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-7ol
296
(2S)-2-(2-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-7-ol
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
297
298
Flv-2.1.1.3 Flavanones
299
Example 4:
300
11
IUPAC
301
302
303
304
flavan-4-one
305
rP
Fo
306
Systematic names
307
2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
308
2-phenyl-2,3-dihydro-4H-chromen-4-one
309
310
ee
Example 5:
311
312
ie
ev
rR
313
314
315
(2S)-4,5,7-trihydroxyflavan-4-one
w
On
316
317
Trivial name
318
naringenin
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 12 of 53
319
320
Systematic names
321
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
322
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
323
324
12
Page 13 of 53
325
Example 6:
326
327
328
rP
Fo
329
330
(2S)-4,5,7-trihydroxy-6,8-bis(3-methylbut-2-en-1-yl)flavan-4-one
331
332
Trivial names
333
6,8-diprenylnaringenin, lonchocarpol A, senegalensein
334
335
Note: The trivial name senegalesein is used in the Dictionary of Flavonoids [4] and is kept as such in the present
recommendations. In the literature the incorrect spelling senegalesien is found in some instances.
rR
ee
336
ev
337
Systematic names
338
339
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl) -6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1benzopyran-4-one
340
341
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl) -6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen4-one
ie
342
343
On
Example 7:
344
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
345
346
347
348
(2R,3R)-3-hydroxyflavan-4-one
13
IUPAC
349
Not: flavanon-3-ol (R-4.1, Table 10 [6]).
350
351
Systematic names
352
(2R,3R)-3-hydroxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
353
(2R,3R)-3-hydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one
354
355
356
Example 8:
357
358
rR
ee
rP
Fo
359
360
(2R,3R) -2,3-dihydroxy-4,7-dimethoxy-8-(3-methylbut-2-en-1-yl)flavan-4-one
361
ev
362
Systematic names
363
364
(2R,3R)-3-hydroxy-2-(2-hydroxy-4-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-2,3dihydro-4H-1-benzopyran-4-one
365
366
(2R,3R)-3-hydroxy-2-(2-hydroxy-4-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-2,3dihydro-4H-chromen-4-one
ie
On
367
368
Flv-2.1.2 Isoflavans
369
Example 9:
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 14 of 53
370
371
372
14
Page 15 of 53
373
374
(3S)-isoflavan-7-ol
375
376
Systematic names
377
(3S)-3-phenyl-7-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one
378
(3S)-3-phenyl-7-hydroxy-2,3-dihydro-4H-chromen-4-one
379
380
381
rP
Fo
Example 10:
382
(1:1)
383
384
385
386
rac-2,4,5,7-tetrahydroxyisoflavan-4-one
Trivial name
389
()-dalbergioidin
388
ie
387
ev
rR
ee
390
On
391
Systematic names
392
rac-3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
393
rac-3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
394
395
Flv-2.1.3 Neoflavans
396
Example 11:
397
15
IUPAC
398
399
400
401
(4R)-neoflavan-7-ol
402
rP
Fo
403
Systematic names
404
(4R)-4-phenyl-3,4-dihydro-2H-1-benzopyran-7-ol
405
(4R)-4-phenyl-3,4-dihydro-2H-chromen-7-ol
ee
406
407
Flv-2.2 Flavones, isoflavones, neoflavones and compounds derived from them
408
409
410
411
Names of flavones, isoflavones and neoflavones can be derived from the names of the respective
functional parents (Figure 2) which already contain one carbonyl group as an implied suffix. When
substituents are among those characteristic groups with a lower priority than ketones, they have to
be cited as prefixes, according to Table 10, Section R-4.1 [6].
ev
rR
412
ie
413
414
11
Figure 2. Functional parents of flavones (5), isoflavones (9) and neoflavones (11). Neoflavones are also
known in the literature as 4-arylcoumarins.
ly
415
416
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 16 of 53
417
418
419
420
421
When the principal characteristic group has a higher priority than a ketone, according to Table 10,
Section R-4.1 [6], names of flavones, isoflavones and neoflavones are derived from the respective
flavan, isoflavan or neoflavan parent hydride. Such groups are radicals, ions, acids, acid derivatives
(anhydrides, esters, acyl halides, amides), nitriles, aldehydes and chalcogen analogues of aldehydes.
422
423
424
Flavones, isoflavones and neoflavones containing a substructure with more than one carbonyl group
are named systematically on the basis of the respective parent hydride modified by the appropriate
suffix, i.e. -dione, -trione, etc.
16
Page 17 of 53
425
Flv-2.2.1 Flavones
426
Flv-2.2.1.1 Flavone aglycons
427
Example 12:
428
429
430
rP
Fo
431
432
flavone
433
434
Systematic names
435
2-phenyl-4H-1-benzopyran-4-one
436
2-phenyl-4H-chromen-4-one
438
ev
437
rR
ee
Example 13:
ie
439
w
On
440
441
442
443
4,5,7-trihydroxyflavone
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
444
445
Trivial name
446
apigenin
447
448
17
IUPAC
449
Systematic names
450
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
451
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
452
453
Example 14:
454
455
456
ee
rP
Fo
457
458
3,5,7-trihydroxy-4-methoxyflavone
459
Trivial name
461
diosmetin
ie
462
ev
460
rR
463
Systematic names
464
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
465
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
On
466
467
Example 15:
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 18 of 53
468
469
470
471
18
Page 19 of 53
472
473
2-(piperidin-1-yl)ethyl 3-methyl-4-oxoflav-2-ene-8-carboxylate
474
475
Not: 2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2,3-didehydroflavan-8-carboxylate because of rule RF8.1 on introduction of unsaturation in parent names ending with an[10].
476
477
Trivial name
478
flavoxate
479
Note: flavoxate is an International Nonproprietary Name (INN) for the anticholinergic drug.
480
rP
Fo
481
Systematic names
482
2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate
483
2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate
484
485
Flv-2.2.1.2 Flavone glycosides
486
Example 16:
ev
rR
ee
487
ie
488
489
490
491
7-(-D-glucopyranosyloxy)-4,5-dihydroxy-3-methoxyflavone
492
493
Trivial name
494
7-O--D-glucopyranosylchrysoeriol
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
495
496
Systematic names
497
7-(-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
19
IUPAC
498
7-(-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
499
500
Example 17:
501
OH
HO
HOH2C
CH3
OH
3'
OCH3
4'
O
7
2
5
OH
OH
OH
O
ee
HOH2C
OH
OH
(a)
ie
ev
rR
503
HO
HO
502
OH
HO
rP
Fo
504
(b)
505
506
Note: Saccharide moiety in Mills depiction (a) and in a conformational form (b).
508
ly
507
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 20 of 53
509
510
7-{-D-glucopyranosyl-(12)--D-glucopyranosyl-(12)-[-L-rhamnopyranosyl-(16)]--Dglucopyranosyloxy}-3,5-dihydroxy-4-methoxyflavone
511
512
513
Trivial name
20
Page 21 of 53
514
515
7-O-{-D-glucopyranosyl-(12)--D-glucopyranosyl-(12)-[-L-rhamnopyranosyl-(16)]--Dglucopyranosyl}diosmetin
516
517
518
Not: diosmetin 7--D-glucopyranosyl- (12) --D-glucopyranosyl- (12) - [-Lrhamnopyranosyl- (16)]--D-glucopyranoside (because it specifies the oxygen atom at position 7
twice)
519
520
Systematic names
521
522
7-{-D-glucopyranosyl-(12)--D-glucopyranosyl-(12)-[-L-rhamnopyranosyl-(16)]--Dglucopyranosyloxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
523
524
7-{-D-glucopyranosyl-(12)--D-glucopyranosyl-(12)-[-L-rhamnopyranosyl-(16)]--Dglucopyranosyloxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
525
Example 18:
ee
526
rP
Fo
527
528
529
ie
ev
rR
530
531
methyl (4,5-dihydroxy-4-oxoflav-2-en-7-yl 2-O-acetyl--D-glucopyranosid)uronate
532
533
534
Not: methyl (4,5-dihydroxy-4-oxo-2,3-didehydroflavan-7-yl 2-O-acetyl--Dglucopyranosid)uronate because of rule RF-8.1 on introduction of unsaturation in parent names
ending with an [10].
535
536
537
Not: methyl (4,5-dihydroxyflavon-7-yl 2-O-acetyl--D-glucopyranosid)uronate because doubled

suffixes such as on-7-yl (which is one + yl) are not permitted in IUPAC chemical
nomenclature.
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
538
539
Trivial name
540
7-O-(methyl 2-O-acetyl--D-glucopyranosyluronate)apigenin
541
542
Not: methyl [apigenin 7-(2-O-acetyl--D-glucopyranosiduronate)] (because it specifies the oxygen

atom at position 7 twice)
21
IUPAC
543
544
Note: The general rule that a name cannot contain two suffixes can be sometimes infringed in carbohydrate
nomenclature, such as with yluronate in the trivial name (see 2-Carb-22 in [9]).
545
546
Systematic names
547
548
methyl [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-acetyl--Dglucopyranosid]uronate
549
550
methyl [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-acetyl--Dglucopyranosid]uronate
rP
Fo
551
552
Flv-2.2.1.3 C-Glycosyl substituted flavones
553
554
555
556
Compounds arising formally from the elimination of water from the anomeric hydroxy group and a
hydrogen atom bound to a carbon atom (thus creating a CC bond) are named using the appropriate
glycosyl group [8]. In the past they have been named as flavonoid Cglycosides, but this
terminology should not be used (2-Carb33.7 [9]).
ee
557
558
rR
Example 19:
559
ie
ev
560
On
561
562
563
6-(-D-glucopyranosyl)-4,5,7-trihydroxyflavone
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 22 of 53
564
565
Trivial names
566
isovitexin
567
6-(-D-glucopyranosyl)apigenin
568
Not: 6-C--D-glucopyranosylapigenin
569
22
Page 23 of 53
570
Systematic names
571
6-(-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
572
6-(-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
573
574
Example 20:
575
576
577
ee
rP
Fo
578
579
6-(-D-glucopyranosyl)-4,5-dihydroxy-7-methoxyflavone
580
581
Trivial name
582
6-(-D-glucopyranosyl)-7-O-methylapigenin
ie
583
ev
rR
584
Systematic names
585
6-(-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
586
6-(-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
On
587
588
Example 21:
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
589
590
23
IUPAC
591
592
593
6,8-di-(-L-arabinopyranosyl)-4,5,7-trihydroxyflavone
594
595
Trivial name
596
6,8-di-(-L-arabinopyranosyl)apigenin
597
Not: apigenin 6,8-di-C--L-arabinopyranoside
598
rP
Fo
599
Systematic names
600
6,8-di-(-L-arabinopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
601
6,8-di-(-L-arabinopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
ee
602
603
Example 22:
rR
604
ie
ev
605
On
606
607
608
6-(-L-arabinopyranosyl)-8-(-D-glucopyranosyl)-3,4,5,7-tetrahydroxyflavone
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 24 of 53
609
610
Trivial names
611
isocarniloside
612
6-(-L-arabinopyranosyl)-8-(-D-glucopyranosyl)luteolin
613
Not: luteolin 6-C--L-arabinopyranosyl-8--D-glucopyranoside
614
24
Page 25 of 53
615
Systematic names
616
617
6-(-L-arabinopyranosyl)-2-(3,4-dihydroxyphenyl)-8-(-D-glucopyranosyl)-5,7-dihydroxy-4H-1benzopyran-4-one
618
619
6-(-L-arabinopyranosyl)-2-(3,4-dihydroxyphenyl)-8-(-D-glucopyranosyl)-5,7-dihydroxy-4Hchromen-4-one
620
621
Example 23:
622
rP
Fo
623
624
rR
ee
625
626
4,5,7-trihydroxy-6-[-D-rhamnopyranosyl-(16)--D-glucopyranosyl]flavone
627
ev
628
Trivial names
629
dulcinoside
630
6-[-D-rhamnopyranosyl-(16)--D-glucopyranosyl]apigenin
631
Not: 6-C- [6-O-(-D-rhamnopyranosyl)--D-glucopyranosyl]apigenin
ie
On
632
633
Systematic names
634
635
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[-D-rhamnopyranosyl-(16)--D-glucopyranosyl]-4H-1benzopyran-4-one
636
637
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[-D-rhamnopyranosyl-(16)--D-glucopyranosyl]-4Hchromen-4-one
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
638
639
Flv-2.2.1.4 Flavonols and flavonol glycosides
640
Example 24:
641
25
IUPAC
642
643
644
645
3-hydroxyflavone
646
rP
Fo
647
Systematic name
648
3-hydroxy-2-phenyl-4H-chromen-4-one
649
650
Example 25:
651
CH3
OH
O
4'
HO
O
7
HO
HO
2
4
OH
CH3
O
OH
O
O
ie
OH
OH
OCH3
O
HO
ev
652
OH
OH
CH3
HO
rR
ee
O
653
654
655
656
4-hydroxy-3-{4-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl]-[-L-rhamnopyranosyl-(12)][-L-rhamnopyranosyl-(16)]--D-galactopyranosyloxy}-7-(-L-rhamnopyranosyloxy)flavones
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 26 of 53
657
658
Systematic names
659
660
661
3-{4-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-[-L-rhamnopyranosyl-(12)]-[-Lrhamnopyranosyl-(16)]--D-galactopyranosyloxy}-2-(4-hydroxyphenyl)-7-(-Lrhamnopyranosyloxy)-4H-1-benzopyran-4-one
662
663
664
3-{4-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-[-L-rhamnopyranosyl-(12)]-[-Lrhamnopyranosyl-(16)]--D-galactopyranosyloxy}-2-(4-hydroxyphenyl)-7-(-Lrhamnopyranosyloxy)-4H-chromen-4-one
665
26
Page 27 of 53
666
Flv-2.2.2 Isoflavones and isoflavone glycosides
667
Flv-2.2.2.1 Isoflavone aglycons
668
Example 26:
669
670
671
rP
Fo
672
673
isoflavone
674
ee
675
Systematic name
676
rR
677
678
Example 27:
ev
679
ie
680
681
682
683
4,5,7-trihydroxyisoflavone
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
684
685
Trivial name
686
genistein
687
688
Systematic names
689
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
690
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
27
IUPAC
691
692
Flv-2.2.2.2 Isoflavone glycosides
693
Example 28:
694
695
rP
Fo
696
697
698
7-(-D-glucopyranosyloxy)-4,5-dihydroxyisoflavone
699
700
Trivial names
701
genistin
702
7-O-(-D-glucopyranosyl)genistein
ev
703
rR
ee
704
Systematic names
705
7-(-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
706
7-(-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
ie
707
Flv-2.2.3 Neoflavones and neoflavone glycosides
709
Flv-2.2.3.1 Neoflavone aglycons
710
Example 29:
ly
708
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 28 of 53
711
712
713
714
28
Page 29 of 53
715
neoflavone
716
717
Trivial name
718
4-phenylcoumarin
719
720
Systematic names
721
4-phenyl-2H-1-benzopyran-2-one
722
rP
Fo
723
724
Example 30:
725
726
727
729
4,6-dihydroxy-7-methoxyneoflavone
ie
728
ev
rR
ee
730
731
Trivial name
732
melannin
On
733
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
734
Systematic names
735
6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-1-benzopyran-2-one
736
6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one
737
738
Flv-2.2.3.2 Neoflavone glycosides
739
Example 31:
29
IUPAC
740
741
742
743
744
7-(-D-glucopyranosyloxy)-8-methylneoflavone
745
rP
Fo
746
Trivial name
747
7-(-D-glucopyranosyloxy)-8-methyl-4-phenylcoumarin
748
ee
749
Systematic names
750
7-(-D-glucopyranosyloxy)-8-methyl-4-phenyl-2H-1-benzopyran-2-one
751
7-(-D-glucopyranosyloxy)-8-methyl-4-phenyl-2H-chromen-2-one
752
ev
rR
753
Flv-2.3 Chalcones and dihydrochalcones
754
755
756
757
758
759
760
761
There is ambiguity in the literature concerning the numbering of the carbon atoms in chalcone.
Most authors, following IUPAC rule C-313.2 [8] as applied with acylaryl ketones such as
acetophenone, have assigned primed numbers to atoms in the phenyl ring attached to the carbonyl
group, and unprimed numbers to atoms in the other phenyl group. Atoms of the ethene-1,2-diyl
linker have been designated and . Some authors have used a reverse system, assigning unprimed
numbers to the phenyl ring attached to the carbonyl group and primed numbers to the other phenyl
ring. [The latter usage correlates with the numbering scheme in the flavan parent structure (Flv1.1.1.1) that arises biosynthetically from a chalcone.]
762
763
764
Because of this ambiguity, the term chalcone has been restricted since 1993 to its use as a retained
name of Type 3, no substitution (R-9.1, table 27a, ref. 6), and individual substituted chalcones are
named systematically, based usually on (2E)-prop-2-en-1-one.
765
766
767
768
769
The Dictionary of Flavonoids [5] and other standard sources [ref. 1, for example] adhere
consistently to the numbering of chalcones according to IUPAC rule C-313.2, and the alternative
usage has been largely abandoned. Since the use of Greek letters as locants is now discouraged, it is
now proposed that the term chalcone as a functional parent be retained as a Type 2, Limited
substitution name. This allows substitution in the phenyl rings, except where a substituent has
ie
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 30 of 53
30
Page 31 of 53
770
771
priority over the carbonyl group, in which situation a fully systematic name is required (Examples
33, 34, and 35).
772
773
Example 32:
774
775
776
rP
Fo
777
778
chalcone
779
780
Systematic name
781
(2E)-1,3-diphenylprop-2-en-1-one
782
ev
783
rR
ee
Example 33:
784
ie
On
785
786
787
788
2,5-dihydroxy-4-(N,N-dimethylamino)chalcone
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
789
790
Systematic name
791
(2E)-1-(2,5-dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
792
793
Example 34:
31
IUPAC
794
795
796
797
Systematic name
798
4-[(1E)-3-oxo-3-phenylprop-1-en-1-yl]benzonitrile
799
800
801
rP
Fo
Example 35:
rR
ee
802
803
804
Systematic name
805
2-[(2E)-1-oxo-3-phenylprop-2-en-1-yl]benzoic acid
ie
ev
806
807
Example 36:
808
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 32 of 53
809
810
811
Systematic name
812
1-(4-hydroxy-2-methoxyphenyl)-3-phenylpropan-1-one
813
814
Flv-2.4 Aurones
815
Flv-2.4.1 Aurone aglycons

32
Page 33 of 53
816
Example 37:
817
818
819
820
821
aurone
822
rP
Fo
823
Systematic name
824
(2Z)-2-benzylidene-1-benzofuran-3(2H)-one
ee
825
826
Example 38:
rR
827
ie
ev
828
829
830
831
3,4,4,6-tetrahydroxyaurone
On
832
833
Trivial name
834
aureusidin
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
835
836
Systematic name
837
(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3(2H)-one
838
33
IUPAC
839
Flv-2.4.2 Aurone glycosides
840
Example 39:
841
842
rP
Fo
843
844
6-(-D-glucopyranosyloxy)-4,4-dihydroxyaurone
845
846
Systematic name
847
848
(2Z)-6-(-D-glucopyranosyloxy)-4-hydroxy-2-[(4-hydroxyphenyl)methylidene]-1-benzofuran3(2H)-one
rR
ee
849
850
Flv-2.5 Anthocyanidins and anthocyanidin 3-glycosides (anthocyanins)
851
Flv-2.5.1 Anthocyanidins
852
853
Anthocyanidins contain a flavylium ion (2-phenylchromenylium, 2-phenyl-14-benzopyran-1ylium) as a parent structure.
ie
ev
854
855
Example 40:
On
856
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 34 of 53
857
858
859
860
3,3,4,5,7-pentahydroxyflavylium
861
34
Page 35 of 53
862
Trivial name
863
cyanidin
864
865
Systematic names
866
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-14-benzopyran-1-ylium
867
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromenylium
868
rP
Fo
869
Flv-2.5.2 Anthocyanins
870
Example 41:
871
872
873
ie
ev
rR
ee
874
875
3-(-D-glucopyranosyloxy)-3,4,5,7-tetrahydroxyflavylium
876
877
Trivial name
878
3-O--D-glucopyranosylcyanidin
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
879
880
Systematic names
881
2-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-5,7-dihydroxy-14-benzopyran-1-ylium
882
2-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-5,7-dihydroxychromenylium
883
884
Example 42:
885
35
IUPAC
OH
OH
3'
HO
4'
O
7
5
2
3
OH
O
OH
OH
O
OH
O
O
886
887
OH
rP
Fo
888
889
890
3-{6-O-[(E)-3-(4-hydroxyphenyl)acryloyl]--D-glucopyranosyloxy}-3,4,5,7tetrahydroxyflavylium
891
ee
892
Trivial name
893
3-O-{6-O-[(2E)-3-(4-hydroxyphenyl)acryloyl]--D-glucopyranosyl}cyanidin
894
ev
rR
895
Systematic names
896
897
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]--Dglucopyranosyloxy}-14-benzopyran-1-ylium
898
899
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]--Dglucopyranosyloxy}chromenylium
ie
On
900
901
Example 43:
902
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 36 of 53
36
Page 37 of 53
OH
OH
3'
HO
4'
O
2
3
7
5
OH
OH
O
OH
OH
O
OH
H3C
903
904
OH
rP
Fo
HO
905
906
3-[-L-rhamnopyranosyl-(16)--D-glucopyranosyloxy]-3,4,5,7-tetrahydroxyflavylium
907
908
Trivial name
909
3-O--rutinosylcyanidin
910
ev
rR
ee
911
Systematic names
912
913
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[-L-rhamnopyranosyl-(16)--D-glucopyranosyloxy]14-benzopyran-1-ylium
914
915
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[-L-rhamnopyranosyl-(16)--Dglucopyranosyloxy]chromenylium
ie
916
917
On
Example 44:
918
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
919
920
37
IUPAC
921
922
3,7-bis(-D-glucopyranosyloxy)-3,4,5-trihydroxyflavylium
923
924
Trivial name
925
3,7-di-O-(-D-glucopyranosyl)cyanidin
926
927
Note: The multiplicative prefix di is used with non-substituted substituents, but with substituted substituents bis
must be used (R-0.1.4 in [1]).
928
rP
Fo
929
Systematic names
930
2-(3,4-dihydroxyphenyl)-3,7-bis(-D-glucopyranosyloxy)-5-hydroxy-14-benzopyran-1-ylium
931
2-(3,4-dihydroxyphenyl)-3,7-bis(-D-glucopyranosyloxy)-5-hydroxychromenylium
ee
932
933
Flv-2.6 Flavonoids containing additional fused/spiro rings in their structures
934
935
Locants for additional rings must be double primed to prevent confusion with those for the phenyl
ring, which are already single primed.
rR
936
Flv-2.6.1 Flavones
938
Example 45:
ie
937
ev
939
w
On
940
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 38 of 53
941
942
943
5-hydroxy-6,7-[methylenebis(oxy)]flavones
944
945
Systematic names
946
9-hydroxy-6-phenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one
947
9-hydroxy-6-phenylpyrano[2,3-f][1,3]benzodioxol-8-one
38
Page 39 of 53
948
949
Flv-2.6.2 Chalcones
950
Example 46:
951
952
953
rP
Fo
954
955
3,4-[methylenebis(oxy)]chalcone
ee
956
957
Systematic names
958
(2E)-3-(1,3-benzodioxol-5-yl)-1-phenylprop-2-en-1-one
rR
959
Flv-2.6.3 Aurones
961
Example 47:
ie
960
ev
962
w
On
963
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
964
965
966
2-methoxy-2,21-dihydrofuro[2,3:6,7]aurone
967
968
Trivial name
969
castillene A
970
39
IUPAC
971
Systematic name
972
2-benzyl-2-methoxybenzo[1,2-b:3,4-b]difuran-3(2H)-one
973
974
Example 48:
975
rP
Fo
976
977
978
979
3,4,4,5,6-pentahydroxy-3,6-dihydropyrano[2,3,4,5:2,21,1,2]aurone
980
Trivial name
982
crombenin
983
ev
rR
981
ee
984
Systematic name
985
4,4,6,6,7-pentahydroxy-1,4-dihydro-3H-spiro[1-benzofuran-2,3-[2]benzopyran]-3-one
ie
986
Flv-2.6.4 Anthocyanidins/Anthocyanins
988
Example 49:
On
987
989
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 40 of 53
990
991
40
Page 41 of 53
992
993
6-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-4,7-dihydroxy-3,5dimethoxypyrano[4,3,2:4,4a,5]flavylium
994
995
996
Trivial name
997
vitisin A
998
999
rP
Fo
Systematic names
1000
1001
5-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-8-hydroxy-2-(4-hydroxy-3,5dimethoxyphenyl)pyrano[4,3,2-de]-14-benzopyran-1-ylium
1002
1003
5-(3,4-dihydroxyphenyl)-3-(-D-glucopyranosyloxy)-8-hydroxy-2-(4-hydroxy-3,5dimethoxyphenyl)pyrano[4,3,2-de]chromenylium
ee
1004
1005
Example 50:
rR
1006
ie
ev
1007
On
1008
1009
1010
3,4,7,8,9-pentahydroxy-6-oxo-6H-[1,5]dioxaphenaleno[43a,3,2:3,4,4a,5]flavylium
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
1011
1012
Trivial name
1013
rosacyanin B
1014
1015
Systematic name
1016
11-(3,4-dihydroxyphenyl)-4,5,8-trihydroxy-2H-1,6-dioxa-10-oxoniabenzo[cd]pyren-2-one
41
IUPAC
1017
Flv-2.6.5 Pterocarpans
1018
1019
Although simple pterocarpans are ring-closure products of isoflavonoids, systematic numbering is

used [8,11].
1020
1021
Note: Systematic numbering and names of the pterocarpan skeleton are given below:
1022
1023
1024
rP
Fo
1025
Systematic names
1026
(6aR,11aR)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c][1]benzopyran
1027
(6aR,11aR)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene
rR
ee
1028
1029
Example 51:
1030
ie
ev
1031
1032
1033
1034
9-methoxypterocarpan-3-ol
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 42 of 53
1035
1036
Trivial name
1037
(-)-medicarpin
1038
1039
Systematic names
1040
(6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c][1]benzopyran-3-ol
1041
(6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol
42
Page 43 of 53
1042
1043
Example 52:
1044
1045
1046
rP
Fo
1047
Semi-systematic names
1048
3,9-dihydroxypterocarp-6a-en-6-one
1049
3,9-dihydroxycoumestan-6-one
1050
1051
Not: 3,9-dihydroxy-6a,11a-didehydropterocarpan-6-one, because of rule RF-8.1 on introduction of

unsaturation in parent names ending with an [10].
ee
1052
1053
Trivial name
1054
Coumestrol
ev
rR
1055
1056
Systematic names
1057
3,9-dihydroxy-6H-[1]benzofuro[3,2-c][1]benzopyran-6-one
1058
3,9-dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one
Flv-2.6.6 Rotenoids
1061
Example 53:
ly
1060
On
1059
ie
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
1062
1063
1064
1065
1066
rotenane
43
IUPAC
1067
1068
Systematic names
1069
(6aS,12aS)-6,6a,12,12a-tetrahydro[1]benzopyrano[3,4-b][1]benzopyran
1070
(6aS,12aS)-6,6a,12,12a-tetrahydrochromeno[3,4-b]chromene
1071
1072
Example 54:
1073
1074
1075
ee
rP
Fo
1076
1077
5-hydroxy-4,5,7-trimethoxyrotenan-4-one
1078
1079
Trivial name
1080
sermundone
ie
ev
rR
1081
1082
Systematic names
1083
1084
(6aS,12aS)-11-hydroxy-2,3,9-trimethoxy-6a,12a-dihydro[1]benzopyrano[3,4-b][1]benzopyran12(6H)-one
1085
(6aS,12aS)-11-hydroxy-2,3,9-trimethoxy-6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 44 of 53
1086
1087
Example 55:
1088
1089
44
Page 45 of 53
1090
1091
1092
(5R)-4,5-dimethoxy-5-(prop-1-en-2-yl) -4,5-dihydrofuro[2,3:7,8]rotenan-4-one
1093
1094
Trivial name
1095
(5R)-4,5-dimethoxy-5-(prop-1-en-2-yl)- 4,5-dihydrofuro[2,3:7,8]rotenone
1096
rP
Fo
1097
Systematic names
1098
1099
(2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydro[1]benzopyrano[3,4b]furo[2,3-h][[1]benzopyran]-6(6aH)-one
1100
1101
(2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3h]chromen-6(6aH)-one
ee
1102
1103
rR
Example 56:
1104
ie
ev
1105
On
1106
1107
1108
(5R)-4,5-dimethoxy-5-(prop-1-en-2-yl)-4,5-dihydrofuro[2,3:7,8]roten-2-ene-21,4-dione
1109
Not: (5R)-4,5-dimethoxy-5-(prop-1-en-2-yl)-2,3-didehydro-4,5dihydrofuro[2,3:7,8]rotenane-21,4-dione, because of rule RF-8.1 on introduction of unsaturation

in parent names ending with an [10].
1110
1111
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
1112
1113
Systematic names
1114
1115
(2R)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2-dihydro[1]benzopyrano[3,4-b]furo[2,3h][[1]benzopyran]-6,12-dione
45
IUPAC
1116
1117
(2R)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2-dihydrochromeno[3,4-b]furo[2,3-h]chromene-6,12dione
1118
1119
Example 57:
1120
rP
Fo
1121
1122
1123
1124
6,6-dimethyl-5,6-dihydro-4H-1,3-dioxolo[4,5:4,5]pyrano[2,3:7,8]rotenan-4-one
ee
1125
1126
Trivial name
1127
millettone
ev
rR
1128
1129
Systematic names
1130
1131
(5aS,12bS)-2,2-dimethyl-5a,12b-dihydro-2H-[1,3]dioxolo[4,5-g]pyrano[2,3-c:6,5f]bis[1]benzopyran-13(6H)-one
1132
1133
(5aS,12bS)-2,2-dimethyl-5a,12b-dihydro-2H-[1,3]dioxolo[4,5-g]pyrano[2,3-c:6,5-f]dichromen13(6H)-one
ie
On
1134
1135
1136
Example 58:
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 46 of 53
1137
1138
1139
46
Page 47 of 53
1140
1141
1142
(2R,3R,5R,6R)-3-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-5-(hydroxymethyl)-5,6dihydro[1,4]dioxino[2,3:3,4]flavan-4-one
1143
Trivial names
1144
silibinin, also called silybin
1145
1146
Systematic names
1147
1148
(2R,3R)-3-hydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4benzodioxin-6-yl]-2,3-dihydro-4H-1-benzopyran-4-one
1149
1150
(2R,3R)-3-hydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one
1151
ee
rP
Fo
1152
1153
1154
1155
1156
Biflavonoids and other flavonoid oligomers have been widely reported in the flavonoid literature
[12-16] and are also included in the present recommendations. The recommended semi-systematic
names consider the terminal flavonoid as the preferred one that is substituted by the other
components. If the flavonoids are identical, the lower locant is linked to the higher one.
ev
rR
1157
1158
Example 59:
ie
1159
w
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
1160
1161
1162
1163
[(3R)-4-methoxyisoflavan-2,7-diol]-(34)-[(3S,4R)-4-methoxyisoflavan-2,7-diol]
1164
1165
Systematic names
47
IUPAC
1166
1167
(3S,4R)-4-{4-hydroxy-5-[(3R)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl]-2-methoxyphenyl}3-(2-hydroxy-4-methoxyphenyl)-3,3-dihydro-2H-1-benzopyran-7-ol
1168
1169
(3S,4R)-4-{4-hydroxy-5-[(3R)-7-hydroxy-3,4-dihydro-2H-chromen-3-yl]-2-methoxyphenyl}-3-(2hydroxy-4-methoxyphenyl)-3,3-dihydro-2H-chromen-7-ol
1170
1171
Example 60:
1172
OCH3
rP
Fo
4'
H3CO
7
5
OH
2'
HO
O
OH
4' 3'
ee
OH
1173
OH
1174
rR
1175
1176
[(2S)-5-hydroxy-4,7-dimethoxyflavan-4-one]-(26)-[(2S)-3,4,5,7-tetrahydroxyflavan-4-one]
ie
ev
1177
1178
Trivial name
1179
[(2S)-4,7-di-O-methylnaringenin]-(26)-[(2S)-3-hydroxynaringenin]
On
1180
1181
Systematic names
1182
1183
(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-{2-[(2S)-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro2H-1-benzopyran-2-yl]-5-methoxyphenyl}-2,3-dihydro-4H-1-benzopyran-4-one
1184
1185
(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-{2-[(2S)-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro2H-chromen-2-yl]-5-methoxyphenyl}-2,3-dihydro-4H-chromen-4-one
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 48 of 53
1186
1187
Example 61:
1188
48
Page 49 of 53
OH
HO
2'
4'
3'
OH
7
5
OH
HO
OH
6
5
O
4
OH
O
4'
HO
O
7
6
3'
OH
2'
4'
1189
3'
OH
OH
OH
rP
Fo
1190
1191
1192
1193
(3,4,5,7-tetrahydroxyflavone)-(26)-(3,4,5,7-tetrahydroxyflavone)-(26)-(3,4,5,7tetrahydroxyflavone)
ee
1194
1195
Systematic names
1196
1197
1198
2-{2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-6-yl]-3,4dihydroxyphenyl}-6-{2-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-3,4-dihydroxyphenyl}-5,7dihydroxy-4H-1-benzopyran-4-one
1199
1200
1201
2-{2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]-3,4-dihydroxyphenyl}-6{2-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-3,4-dihydroxyphenyl}-5,7-dihydroxy-4H-chromen-4one
1202
Note: In order to facilitate interpretation of the systematic name, systematic numbering is given below:
ie
ev
rR
1203
OH
HO
OH
O HO
OH
6 7
ly
OH
1204
4
3
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
O
4
OH
O
HO
O
7
6
2
5
OH
OH
2
4
OH
OH
1205
1206
49
IUPAC
1207
Example 62:
1208
1209
1210
rP
Fo
1211
1212
(5,7-dihydroxyflavone)-(4-epoxy-6)-(4,5,7-trihydroxyflavone)
1213
1214
Trivial name
1215
hinokiflavone
ee
1216
rR
1217
Systematic names
1218
1219
6-[4-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)4H-1-benzopyran-4-one
1220
1221
6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4Hchromen-4-one
ie
ev
1222
1223
Example 63:
On
1224
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 50 of 53
1225
1226
1227
1228
[(3R)-2-methoxyisoflavan-3,7-diol]-(4-epoxy-4)-[(3R)-2-methoxyflavan-3,7-diol]
1229
1230
50
Page 51 of 53
1231
Trivial name
1232
biscyclolobin
1233
1234
Systematic names
1235
3,3-oxybis(3-hydroxy-2-methoxy-4,1-phenylene)bis[(3R)-3,4-dihydro-2H-1-benzopyran-7-ol]
1236
3,3-oxybis(3-hydroxy-2-methoxy-4,1-phenylene)bis[(3R)-3,4-dihydro-2H-chromen-7-ol]
1237
1238
1239
rP
Fo
Example 64:
1240
1241
ie
ev
rR
ee
1242
1243
(3,4,5,7-tetrahydroxyflavone)-2-(28,82)-(3,4,5,7-tetrahydroxyflavone)
1244
1245
Trivial name
1246
Anhydrobartramiaflavone
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
1247
1248
Systematic names
1249
1250
15,16,25,27,35,36,45,47-octahydroxy-1,3(1,2)-dibenzena-2,4(2,8)-bis(4H-1benzopyrana)cyclotetraphane-24,44-dione
1251
1252
15,16,25,27,35,36,45,47-octahydroxy-1,3(1,2)-dibenzena-2,4(2,8)-di(4H-chromena)cyclotetraphane24,44-dione
1253
1254
51
IUPAC
1255
MEMBERSHIP OF SPONSORING BODIES
1256
1257
1258
1259
1260
1261
1262
1263
1264
1265
1266
Membership of the IUPAC Division (VIII) of Chemical Nomenclature and Structure Representation
for (a) the period 2010-2011; (b) 2012. (a) President Richard Hartshorn; Past-President Gerard
Moss; Secretary Ture Damhus; Titular Members Jonathan Brecher, Kirill Degtyarenko, Philip
Hodge, Alan Hutton, Jeff Leigh, Jeffery Wilson, Andrey Yerin; Associate Members Karl-Heinz
Hellwich, Jaroslav Kahovec, Ebbe Nordlander, Jzsef Nyitrai, Warren Powell, Jan Reedijk;
National Representatives: Sundarababu Baskaran, Abdul Jalil Miah, Patrick Moyna, Hiroshi Ogino,
Amlia Rauter, Ricardo Bicca de Alencastro.(b) President Richard Hartshorn; Vice-President KarlHeinz Hellwich; Secretary Ture Damhus; Titular members Michael Beckett; Ebbe Nordlander;
Warren Powell; Amlia P. Rauter; Hinnerk Rey; Antony Williams; Andrey Yerin; Associate
Members Kirill Degtyarenko; Philip Hodge; Alan Hutton; Jan Reedijk; Nigel Wheatley; Jeffrey
Wilson; National Representatives Vefa Ahsen; Itrat Anis; Sundarababu Baskaran; Gernot Eller;
Md. Hashem; Wei Huang; Jaroslav Kahovec; Lupituko Mkayula; Jzsef Nagy; Supawan
Tantayanon.
ie
ev
rR
ee
1267
1268
1269
1270
1271
1272
1273
1274
1275
1276
1277
1278
1279
Membership of the IUPAC-IUBMB Joint Commission on Biochemical Nomenclature for (a) the
period of 20102012; (b) present membership: (a)Chair Dietmar Schomburg; Secretary Richard
Cammack; Titular members Gerard Moss; Keith Tipton; Johannes Vliegenthart; Associate members
Kristian Axelsen; Ron Caspi; Athel Cornish-Bowden; Derek Horton. (b) Titular members NCIUBMB and JCBN Chair Gerard Moss; Secretary Richard Cammack; NC-IUBMB Ron Caspi;
Andrew McDonalds; Dietmar Schomburg; NC-IUBMB and JCBN: Kristian Axelsen; Keith Tipton;
JCBN: Markus Ennis; Associate members NC-IUBMB Ida Schomburg; Johannes Vliegenthart;
JCBN Athel Cornish-Bowden; Derek Horton; Karl-Heinz Hellwich; Ture Damhus; Amelia P.
Rauter.
rP
Fo
1280
1281
REFERENCES
On
1282
1284
1. Flavonoids Chemistry, Biochemistry and Applications (.M.Andersen, K. R. Markham,

eds.), CRC Press, Taylor and Francis Group, Boca Raton (2006).
1285
2. The Science of Flavonoids (E. Grotewold, ed.), Springer, New York (2006).
1286
1287
3. Flavonoids and Related Compounds: Bioavailability and Function (J. P. E. Spencer, A.

Crozier, eds.), Oxidative Stress and Disease Series, Taylor and Francis, Boca Raton (2012).
1288
4. J. Buckingham. Dictionary of Flavonoids, Taylor and Francis, Boca Raton (2012).
1289
1290
5. J. B. Harborne, H. Baxter. The Handbook of Natural Flavonoids (J. B. Harborne, H. Baxter,

eds.), Vols. 1 and 2, John Wiley, New York (1999).
1283
ly
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Page 52 of 53
52
Page 53 of 53
1291
1292
6. IUPAC. A Guide to IUPAC Nomenclature of Organic Compounds. R. Panico, W. H. Powell,

J.-C. Richer (Eds.), Blackwell Scientific Publications, Oxford (1993).
1293
1294
7. H. A. Favre, K.-H. Hellwich, G. P. Moss, W. H. Powell, J. G. Traynham, Corrections to 'A

Guide to IUPAC Nomenclature of Organic Compounds'. Pure Appl. Chem. 77, 1327 (1999).
1295
1296
1297
8. IUPAC Recommendations 1979. Nomenclature of Organic Chemistry (the 'Blue Book').

Sections A, B, C, D, E, F, H. Prepared for publication by J. Rigaudy and S. P. Klesney. S. P.
Klesney (Ed.), Pergamon Press, Oxford (1979).
1298
1299
9. A. D. McNaught. Nomenclature of carbohydrates (IUPAC Recommendations 1996), Pure

Appl. Chem. 68, 1919 (1996).
1300
1301
1302
10. P. M. Giles, Jr. Section F:Natural Products and Related Compounds, Pure Appl. Chem. 71,
587 (1999); Corrections and modifications: H. A. Favre, P. M. Giles Jr., K.-H. Hellwich, A.
D. McNaught, G. P. Moss, W. H. Powell. Pure Appl. Chem. 76, 1283 (2004).
1303
1304
11.
1305
1306
12. H. Geiger, Biflavonoids and Triflavonoids, in The Flavonoids: Advances in Research since
1986 (J. B. Harborne, ed.), pp 95-115. Chapman & Hall, London (1994).
1307
1308
13. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids: Advances in Research since 1980 (J.
B. Harborne, T. J. Mabry, eds.), pp. 99-124. Chapman & Hall, London (1988).
1309
1310
14. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids (J. B. Harborne, T. J. Mabry, eds.), pp.
505-534. Chapman & Hall, London (1982).
1311
1312
15. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids (J. B. Harborne, T. J. Mabry, H.

Mabry, eds.), pp. 692-742. Chapman & Hall, London (1975).
1313
16. H. D. Lockley, Fortschr. Chem. Org. Naturst. 30, 207 (1973).
rP
Fo
G. P. Moss. Nomenclature of fused and bridged ring systems (IUPAC recommendations

1998), Pure Appl. Chem.70, 143 (1998).
ie
ev
rR
ee
ly
On
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
IUPAC
53

Flavonoides Recommendations

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Flavonoides Recommendations

Uploaded by

Copyright:

Available Formats

Page 1 of 53

(IUPAC Provisional Recommendations)*

Universidade de Lisboa, Faculdade de Cincias, Departamento de Qumica e Bioqumica/Centro de

Flv-1 Flavonoids Definitions and conventions

Flv-1.1 Flavonoid classes with a C6-C3-C6 carbon framework

Flv-1.1.1.2 Flavones and 3-hydroxyflavones (flavonols)

Flv-1.1.1.3 Anthocyanidins/anthocyanins (anthocyanidin 3-glycosides)

Flv-1.1.4 Chalcones and dihydrochalcones

Flv-1.1.6 Pterocarpans and their 3,4-didehydro derivatives (coumestans)

Flv-1.4 Biflavonoids and other flavonoid oligomers

Flv-2 Guide to the construction of semi-systematic names

Flv-2.1 Flavans, isoflavans, neoflavans and compounds derived from them

Flv-2.1.1.2 Flavan glycosides

Flv-2.2 Flavones, isoflavones, neoflavones and compounds derived from them

Flv-2.2.1.1 Flavone aglycons

Flv-2.2.1.2 Flavone glycosides

Flv-2.2.1.3 C-Glycosyl substituted flavones

Flv-2.2.1.4 Flavonols and flavonol glycosides

Flv-2.2.2 Isoflavones and isoflavone glycosides

Flv-2.2.2.1 Isoflavone aglycons

Flv-2.2.2.2 Isoflavone glycosides

Flv-2.2.3 Neoflavones and neoflavone glycosides

Flv-2.2.3.1 Neoflavone aglycons

Flv-2.2.3.2 Neoflavone glycosides

Flv-2.3 Chalcones and dihydrochalcones

Flv-2.4.1 Aurone aglycons

Flv-2.4.2 Aurone glycosides

Flv-2.5 Anthocyanidins and anthocyanidin 3-glycosides (anthocyanins)

Flv-2.6 Flavonoids containing additional fused/spiro rings in their structures

Flv-2.8 Biflavonoids and other flavonoid oligomers

MEMBERSHIP OF SPONSORING BODIES

*Sponsoring bodies: IUPAC Division(VIII) of Chemical Nomenclature and Structure

Corresponding author: Amlia P. Rauter, Universidade de Lisboa, Faculdade de Cincias,

Flv-1 Flavonoids Definition and conventions

The following carbon frameworks characterize the various flavonoid classes:

Flv-1.1 Flavonoid classes with a C6-C3-C6 carbon framework

The flavonoids (2-aryl-1-benzopyrans) are compounds with a skeleton of type 1.

Flv-1.1.1.2 Flavones and 3-hydroxyflavones (flavonols)

Flv-1.1.1.3 Anthocyanidins/anthocyanins (anthocyanidin 3-glycosides)

The isoflavonoids (3-aryl-1-benzopyrans) are compounds derived from 8.

The neoflavonoids (4-aryl-1-benzopyrans) are compounds with parent structure 10.

Neoflavans are compounds with skeleton 10. They may be substituted.

Neoflavones are compounds with skeleton 11. They may be substituted.

Flv-1.1.4 Chalcones and dihydrochalcones

Chalcones are compounds derived from (2E)-1,3-diphenylprop-2-en-1-one (chalcone, compound

Aurones are compounds derived from 14, which is based on (2Z)-2-(arylmethylidene)-1benzofuran-3(2H)-one.

Flv.1.1.6 Pterocarpans and their 3,4-didehydro derivatives (coumestans)

Flv-1.4 Biflavonoids and other flavonoid oligomers

Flv-2 Guide to the construction of semi-systematic names

Flv-2.1 Flavans, isoflavans, neoflavans and compounds derived from them

Flv-2.1.1.1 Flavan aglycons

Flv-2.1.1.2 Flavan glycosides

6,8-diprenylnaringenin, lonchocarpol A, senegalensein

Not: flavanon-3-ol (R-4.1, Table 10 [6]).

Flv-2.2 Flavones, isoflavones, neoflavones and compounds derived from them

Flv-2.2.1.1 Flavone aglycons

Flv-2.2.1.2 Flavone glycosides

methyl (4,5-dihydroxy-4-oxoflav-2-en-7-yl 2-O-acetyl--D-glucopyranosid)uronate

Not: methyl (4,5-dihydroxyflavon-7-yl 2-O-acetyl--D-glucopyranosid)uronate because doubled

Not: methyl [apigenin 7-(2-O-acetyl--D-glucopyranosiduronate)] (because it specifies the oxygen

methyl [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-acetyl--Dglucopyranosid]uronate

methyl [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-acetyl--Dglucopyranosid]uronate

Flv-2.2.1.3 C-Glycosyl substituted flavones

Not: apigenin 6,8-di-C--L-arabinopyranoside