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220108

Sigma-Aldrich

Isovanillic acid

97%

Synonym(s):

3-Hydroxy-4-methoxybenzoic acid

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About This Item

Linear Formula:
HOC6H3(OCH3)CO2H
CAS Number:
645-08-9
Molecular Weight:
168.15
EC Number:
211-430-5
MDL number:
MFCD00002507
UNSPSC Code:
12352100
PubChem Substance ID:
24853164
NACRES:
NA.22

assay

97%

form

solid

mp

250-253 °C (lit.)

SMILES string

COc1ccc(cc1O)C(O)=O

InChI

1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)

InChI key

LBKFGYZQBSGRHY-UHFFFAOYSA-N

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General description

Rate of oxidation of isovanillic acid by washed cells of Pseudomonas putida has been reported.

Application

Isovanillic acid has been used in the synthesis of opiate alkaloid precursor, dihydrothebainone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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M R Jeffers et al.
Microbiology (Reading, England), 143 ( Pt 6), 1975-1981 (1997-06-01)
A methyltransferase enzyme catalysing the 3-O-methylation of isovanillic acid (3-hydroxy-4-methoxybenzoic acid) by S-adenosylmethionine (SAM) was identified in Phanerochaete chrysosporium and purified. Gel filtration indicated an M(r) of 71,000 and SDS-PAGE showed that the enzyme was composed of two subunits of
Widiastuti Setyaningsih et al.
Food chemistry, 288, 221-227 (2019-03-25)
Fifteen phenolic compounds were determined in rice grains by ultrasound assisted extraction and ultra-performance liquid chromatography with photodiode array detection. Primarily, an UAE method has been developed and validated for the extraction of phenolics from rice grains. For the optimization
Preparation of oxygenated phenylacetic acids.
Weller DD, et al.
The Journal of Organic Chemistry, 49(11), 2061-2063 (1984)
I Reenilä et al.
Journal of chromatography. B, Biomedical applications, 663(1), 137-142 (1995-01-06)
We applied coulometric detection (three electrochemical electrodes in series) to quantitate vanillic acid and isovanillic acid using reversed-phase HPLC. The formation of these reaction products from dihydroxybenzoic acid was used as a precise and reproducible measure of catechol-O-methyltransferase (COMT) activity
Zhenya Chen et al.
ACS synthetic biology, 6(9), 1784-1792 (2017-06-07)
Vanillyl alcohol is a phenolic alcohol and is used as a flavoring agent in foods and beverages. In this paper, we propose a novel artificial pathway for microbial production of vanillyl alcohol from simple carbon sources. The pathway extends from
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