2,3-Methylenedioxybenzoic acid

Phenols have distinct odours. Notable simple phenol-related odorants/tastants include 4-methoxybenzaldehyde (/i-anisealdehyde), guaiacol (2-methoxyphenol), 4-hydroxyben-zaldehyde, phenethyl alcohol, piperonal (heliotropin, 3,4-methylenedioxybenzoic acid) and Vanilla planifolia (vanilla) (Orchidaceae) pod vanillin (3-methoxy-4-hydroxybenzaldehyde) (Chapter 10). 

The thitsiol, 1,2-dihydroxy-4-[(ZZ)-heptadeca-8,11-dienyIlbenzene was similarly derived from 3,4-methylenedioxybenzoic acid. 

Me ether [7168-93-6]. 6-Methoxy-l,3-benzodioxole-5-carboxylic acid, 9CI. 6-Methoxy-3,4-methylenedioxybenzoic acid C HgOg M 196.159 Needles (CHCI3). Mp 153-153.2°. 

Piperonylbutoxide (3), tropital (5) and bucaprolate (6) are prepared by the reaction of diethyleneglycol-monobutyiether or its sodium salt with chloromethy-lated dihydrosafrol (7), piperonal dichloride (8) or 2,3-methylenedioxybenzoic acid... 

The ether extract was concentrated to yield a residue of 25.2 mg. 2,3-Methylenedioxybenzoic acid (76) (10.3 (ig) in ether was added to one-fourth of this concentrate, and the mixture was then reduced to dryness. The residue was dissolved in CDCI3 and subjected to H NMR analysis. From the ratio of the integrated methylenedioxy signal of 6 to that given by the known amount of internal standard, it was possible to calculate that the crude extract corresponding to 12 g of the fresh roots contained 64 pg of 6, with fresh roots containing 5.3 pg/g. 

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