CHEMICAL DEFINITIONS

The term sugar alcohol refers in chemical colloquialism to reduction products of sugars
and indicates that all oxygen aoms in a simple sugar alcohol molecul are present in the form
of hydroxyl groups. The sugar alcohols are polyols. This term refers to chemical
compounds containing there or more hydroxil groups, and is synonymous with another
customary term, polyhydric alcohol. The polyols can be divided into acyclic polyols (alditols
or glicitols, which are true sugar alcohols), and the cyclic polyols. An example of the former
is sorbitol, while a common cyclic polyol is myo-inositol. The most important sugar alcohols
that will be discussed in this chapter are based on five-or six-carbon skeletons, and are
therefore called pentitols and hexitols. The alditols can be regarded as derivatives of
hydrocarbons. For example, xylitols is a pentahydroxypentane, or xylo-pentane-1,2,3,4,5
pentol. All of the theoretically possible four-carbon sugar alcohols, tetritols (threitol and
erythritol), are known, as are all stereoisomerically possible pentitols and hexitols. All above
polyols are based on a single monosaccharideskeleton. Among disaccharide sugar alcohols
maltitol, lactitol, and palatinit have received attention in nutrition. Complex, long-chain
polyhydroxy alcohols have been produced for various food uses by chemical reduction of
oligosaccharides and dextrins,. Such procedures normally lead to the formation of mixtures of
polyols of various lengths.
As achemical group, simple, pure sugar alcohols are crystalline substances varying in taste
from faintly sweet (galactitol and lactitol) to very sweet (crythritol and xylitol). This
discussion will be predominantly restricted to pentitols and hexitols among the simple alditols
which can be best considered as reduction products of monosaccharides, and to a few
disaccharides sugar alcohols. For example, although glycerol can be regarded as a simple
sugar alcohol (methanol and ethylene glycol would theoretically be the lowest homologues)
and an important dietary ingredient by virtue og its presence in triglycerides, space does not
allow its treatise. For the same reason several interesting synthetic derivatives of sugar
alcohols must be excluded. From several naturally occurring sugar alcohols (such as
rhamnitol; corresponds to 6-deoxy-L-mannose) there is too little information at this stage.
Table 11-1 list several natural, dietary sugar alcohols and few synthetic products that already
have a place in human nutrition or in certain medical uses, or which have a potential to have
one in the future. Although this author prefers the term alditol for simple straight-chain
polyols derived from aldoses, the term sugar alcohol will nevertheless be employed inthis
chapter.
HISTORIC AND EVOLUTIONARY ASPECTS
Humans and other animal species have consumed certain small amounts of sugar alcohols
during the entire evolution. Although there understandably cannot be any direct reference in
any ancient scripts to the consumption of sugar alcohols (although there are plenty of
historical references to sugar and other sweet items), it is likely that various fruits, fronds,
leaves, and other plant parts consumed by man and other animals have contained certain
concentration levels of known sugar alcohols. The term manna is used for a food that was
miraculously supplied to the Israelites in their journey through the wilderness. Manna was
also used by Arabic nomads(Bodenheimer 1947; Reicke and Rost 1950). Manna also means
the sweetish dried exudate of a European ash (especially Fraxinus ornus) that contains Dmannitol, and a similar product excreted by two closely related species of scale insects

(superfamily Coccoidea). These insect are Trabutina mannipara and Majacoccus serpentinus,
feeding on tamarisk (Tamarix mannifera). It is important to emphasize the habitual
consumtion of such sweet exudates by man since prehistoric times, and the fact that Dmannitol, for example, is frequently found in high concentrations in exudates of plants
(Stacey 1974). Some seaweeds were reported to contain up to 35% mannitol (in dry weight)
(Lohmar 1962; Stacey 1974).
For the understanding of the role of dietary sugar alcohols as one category of
functional foods, it is necessary to refer to the expediency of the evolution of these
carbohydrates. During the evolution of the biosphere, carbohydrates were probably produced
by the polymerization of formaldehyde. The strongly reducing conditions were most likely
inimical to the existence of free aldoses and ketoses (Horecker 1969). The latter would
become stabilized by formation of glycosidic bonds with other molecules (such as purines,
pyrimidines, and other monosaccharides). The remaining aldoses and ketoses would
eventually undergo reduction to corresponding polyhydric alcohols. Therefore, evolution
embraced certain sugar alcohols at the very first stages of the existence of life.
COMMON SUGAR ALCOHOL PROPERTIES
Vvirtually all sugar alcohols share the same type of carbon skeleton with other
natural, dietary carbohydrates, and the sugar alcohols can even be assayed as sugars in
chemical total sugar analyses. All sugar alcohols can be converted chemically or
enzymatically to the corresponding aldoses and ketoses, which in turn are reducible to the
sugar alcohol form. What, then, are the particular chemical features that make sugar alcohols
a special group of carbohydrates ? some of the common denominators of sugar alcohols that
make them biologically unque are as follows.
a) The absence of reducing carbonyl groups- This fact makes sugar alcohols chemically
somewhat less reactive than the coressponding aldoses and ketoses. The sugar
alcohols thus avoid certain chemical reactions that take place at a high rate with
several aldoses and ketoses. The relative chemical inertness is also reflected in the
fact that- in the human oral cavity- the sugar alcohols are less reactive and do not
normally participate in extensive acid formation in dental plaque.
Table 11-1. example of sugar alcohols and their properties