220108
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
211-430-5
MDL number:
Product Name
Isovanillic acid, 97%
InChI key
LBKFGYZQBSGRHY-UHFFFAOYSA-N
InChI
1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)
SMILES string
COc1ccc(cc1O)C(O)=O
assay
97%
form
solid
mp
250-253 °C (lit.)
functional group
carboxylic acid
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Application
Isovanillic acid has been used in the synthesis of opiate alkaloid precursor, dihydrothebainone.
General description
Rate of oxidation of isovanillic acid by washed cells of Pseudomonas putida has been reported.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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
Establishing an Artificial Pathway for De Novo Biosynthesis of Vanillyl Alcohol in Escherichia coli.
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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