94770

Sigma-Aldrich

Vanillic acid

purum, ≥97.0% (HPLC)

Synonym(s):
4-Hydroxy-3-methoxybenzoic acid
Linear Formula:
HOC6H3(OCH3)CO2H
CAS Number:
Molecular Weight:
168.15
Beilstein/REAXYS Number:
2208364
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

purum

assay

≥97.0% (HPLC)

ign. residue

≤0.2%

mp

208-210 °C (lit.)
208-213 °C

SMILES string

COc1cc(ccc1O)C(O)=O

InChI

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

InChI key

WKOLLVMJNQIZCI-UHFFFAOYSA-N

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Application

Vanillic acid is used as a precursor in the synthesis of a wide range of bio-based epoxy resins and polyesters. It is also a key starting material in the total synthesis of barmumycin4 and bosutinib.

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 1

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Aromatic thermotropic polyesters based on 2, 5-furandicarboxylic acid and vanillic acid.
Wilsens C H, et al.
Polymer, 55(10), 2432-2439 (2014)
Novel vanillic acid-based poly (ether?ester) s: from synthesis to properties.
Pang C, et al.
Polym. Chem., 6(5), 797-804 (2015)
Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers.
Aouf C, et al.
Green Chemistry, 14(8), 2328-2336 (2012)
Isolation, structural assignment, and total synthesis of barmumycin.
Lorente A, et al.
The Journal of Organic Chemistry, 75(24), 8508-8515 (2010)
Xiao Jia Yin et al.
Molecules (Basel, Switzerland), 15(6), 4261-4266 (2010-07-27)
This paper reports a novel synthesis of bosutinib starting from 3-methoxy-4-hydroxybenzoic acid. The process starts with esterification of the starting material, followed by alkylation, nitration, reduction, cyclization, chlorination and two successive amination reactions. The intermediates and target molecule were characterized...
Protocols
Protocol for HPLC Analysis of Flavonoids on Ascentis® RP-Amide
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