Synthetic dihydrocapsiate
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Definition

Synthetic dihydrocapsiate is a viscous colorless to yellowish oil that contains more than
94 percent dihydrocapsiate. Dihydrocapsiate, ((4-hydroxy-3-methoxybenzyl)
8-methylnonanoate), has the molecular formula C18H28O4, and a molecular weight of
308.41, with the Chemical Abstracts Service Registry Number 205687-03-2.

Ajinomoto, the manufacturer, indicates that the method of manufacture of synthetic
dihydrocapsiate involves the esterification of vanillyl alcohol (V-OH) and 8-methylnonanoic
acid (MNA) catalyzed by an immobilized lipase preparation. The esterification is followed
by filtration, extraction with n-hexane, and evaporation. Ajinomoto also describes the
manufacturing process for the starting materials V-OH and MNA. MNA is prepared from
isobutyl bromide and 6-bromohexanoic acid ethyl ester through a Grignard coupling
reaction and deprotection process to give a carboxylic acid. V-OH is prepared from
vanillin by reduction, followed by evaporation of the solvent (tetrahydrofuran).

Specifications include limits on lead (less than 1 mg/kg), arsenic (less than 1 mg/kg),
cadmium (less than 1 mg/kg), V-OH (less than 1 percent), other reaction byproducts (less
than 2 percent), and residual solvents, n-hexane and tetrahydrofuran (less than 5 mg/kg).

Dihydrocapsiate occurs naturally in a variety of edible
chili peppers (Capsicum species)
at various concentrations and is consumed as part of the diet.

GRAS Notice No. GRN 000249

SOURCE: FDA website 2010