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Sigma-Aldrich

Vanillic acid

purum, ≥97.0% (HPLC)

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Synonym(s):
4-Hydroxy-3-methoxybenzoic acid
Linear Formula:
HOC6H3(OCH3)CO2H
CAS Number:
121-34-6
Molecular Weight:
168.15
Beilstein:
2208364
EC Number:
204-466-8
MDL number:
MFCD00002551
PubChem Substance ID:
329770384
NACRES:
NA.22

grade

purum

Quality Level

200

Assay

≥97.0% (HPLC)

form

powder

ign. residue

≤0.3%

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

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Novel vanillic acid-based poly (ether?ester) s: from synthesis to properties.
Pang C, et al.
Polym. Chem., 6(5), 797-804 (2015)
Isolation, structural assignment, and total synthesis of barmumycin.
Lorente A, et al.
The Journal of Organic Chemistry, 75(24), 8508-8515 (2010)
Aromatic thermotropic polyesters based on 2, 5-furandicarboxylic acid and vanillic acid.
Wilsens C H, et al.
Polymer, 55(10), 2432-2439 (2014)
Delphine Lamoral-Theys et al.
Bioorganic & medicinal chemistry, 18(11), 3823-3833 (2010-05-15)
A series of 33 novel divanillates and trivanillates were synthesized and found to possess promising cytostatic rather than cytotoxic properties. Several compounds under study decreased by >50% the activity of Aurora A, B, and C, and WEE1 kinase activity at
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