Introduction

During the month of May, in the valleys of the northwestern Pacific coastal regions of the United States, a small plant, bearing the botanical name Limnanthes alba, begins to bloom with such an abundance of delicate, beautiful white flowers that there appears to be a natural foam on the meadow. Meadowfoam is the common name for this plant.

Nomenclature and Chemical Structure

Chemical Name (primary antioxidant): 1,3-di(3-methoxybenzyl) thiourea (3MBTU)
S NH NH

O CH3 H3C

Industrial Crops and Products 16 (2002) 4357

1,3-di(3-Methoxybenzyl) thiourea and related lipid antioxidants _

Thomas P. Abbott a, *, Alan Wohlman b , Terry Isbell a , Frank A. Momany a ,Charles Cantrell a , Donald V. Garlotta a , David Weisleder a a Agricultural Research Service, United States Department of Agriculture, National Center for Agricultural Utilization Research, 1815 North University Street, Peoria, IL 61604, USA b The Fanning Corporation, 2450 W. Hubbard St., Chicago, IL 60612, USA

Chemical and Physical Data

Molecular Formula = C17 H20 N2 O2 S Formula Weight = 316.419 Composition = C(64.53%) H(6.37%) N(8.85%) O(10.11%) S(10.13%) Molar Refractivity = 92.75 0.3 cm3 Molar Volume = 270.0 3.0 cm3 Index of Refraction = 1.602 0.02 Surface Tension = 48.1 3.0 dyne/cm Density = 1.171 0.06 g/cm3 Average Mass = 316.423591 Da

A Note About The Structure Of The Antioxidant

Vacuum free energy (AM 1) favors, by over 6 kcal/mol, the extended trans-trans form of 3MBTU. NMR results are in agreement with the trans-trans conformation of the molecule being preferred in non-polar solvents. In this configuration, the sulfur atom is highly exposed and available to participate in redox reactions. This characteristic of the molecule would most likely contribute to its high antioxidant efficiency.

Sulfur atom Highly exposed and therefore readily available to participate in redox reactions

Initial Identification Of Antioxidant Activity

Meadowfoam (Limnanthes alba) seed oil is highly stable to oxidation. The addition of crude Meadowfoam seed oil to other oils imparts enhanced oxidation stability to the mixture (Isbell et al., 1999). This indicates that crude Meadowfoam seed oil contains an antioxidant

Ability Of 3MBTU To Protect Oils From Oxidation

Oxidative stability index (OSI) values were determined on 5.00 g samples in triplicate according to AOCS method Cd 12b-92 (AOCS, 1993) at 110 and 130 oC

OSI is measured by heating the oil to a definite temperature (110 oC or 130 oC for these experiments). As the oil is heated gases are produced into the headspace above the oil. Theses gases are captured and dissolved in water thereby changing the conductance of the aqueous system. The oil eventually fatigues and there is a very rapid rise in conductance. The time required to fully fatigue (i.e. complete thermal stress of the oil) is called the OSI or Oxidative Stability Index. It is measured in hours, the longer the OSI time the more stable the oil.

OSI (Hrs. @ 110 degrees C)

40.0 35.0 30.0 25.0

Hours

20.0 15.0 10.0 5.0 0.0 OSI

4265 (0.9%) 36.5

4160 (0.9%) 34.2

BHA (1.0%) 18.6

BHT (1.0%) 26.0

CONTROL 6.9

Crambe (refined) + AO 4160 activity as a function of concentration

140.0

120.0

100.0

OSI (hrs) @ 110 oC

80.0

60.0

40.0

20.0

0.0
Cram be Oil (refined) = COr COr + 0.01% AO COr + 0.02% AO COr + 0.1% AO COr + 0.5% AO COr + 1.0% AO