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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:
Molecular Weight:
168.15
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

solid

mp

250-253 °C (lit.)

functional group

carboxylic acid

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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
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
Motohiro Nishimura et al.
Journal of bioscience and bioengineering, 102(2), 124-127 (2006-10-10)
Strain NL15-2K was isolated from soil by screening for bacteria capable of catabolizing lignin-related aromatic acids. This isolate was identified as a Streptomyces sp. on the basis of morphology and an analysis of its 16S rRNA gene sequence. NL15-2K utilized

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