Vanillic acid Chemical Properties

Melting point:

208-210 °C(lit.)

Boiling point:

257.07°C (rough estimate)

Density 

1.3037 (rough estimate)

refractive index 

1.5090 (estimate)

FEMA 

3988 | 4-HYDROXY-3-METHOXYBENZOIC ACID

storage temp. 

Store below +30°C.

solubility 

Acetonitrile (Slightly), Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly）

form 

Liquid

pka

pKa 4.53(H2O t = 25 c = 0.016–0.001) (Uncertain)

color 

Clear colorless to brown, may darken during storage

Odor

at 100.00 %. dairy milky custard creamy powdery vanilla bean

Odor Type

creamy

Water Solubility 

Soluble in water, alcohol and ether.

Merck 

14,9931

JECFA Number

959

BRN 

2208364

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

WKOLLVMJNQIZCI-UHFFFAOYSA-N

LogP

1.30

CAS DataBase Reference

121-34-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-hydroxy-3-methoxy-(121-34-6)

EPA Substance Registry System

Vanillic acid (121-34-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

WGK Germany 

1

RTECS 

YW5300000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29189090

MSDS

• Language:English Provider:4-Hydroxy-3-methoxybenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Vanillic acid Usage And Synthesis

Description

Vanillic acid is a dihydroxybenzoic acid that can be used as a flavoring agent. As an oxidized form of vanillin, it is the intermediate product during the two-step bioconversion process from ferulic acid to vanillin. It exists in high amount in the root of Angelica sinenisis, which is a plant used in traditional Chinese medicine. It also exists in acal oil, argan oil as well as wine and vinegar. It can be used in the synthesis of the analeptic drug etamivan, modecainide, brovanexine, vanitiolide, and vanyldisulfamide. It can be manufactured through the oxidation of vanillin to the carboxylic acid.

References

https://en.wikipedia.org/wiki/Vanillic_acid
https://pubchem.ncbi.nlm.nih.gov/compound/Vanillic_acid#section=Top

Chemical Properties

4-Hydroxy-3-methoxybenzoic acid has a vanilla-like odor and taste.

Chemical Properties

white odourless crystals or powder

Occurrence

Reported found in guava, grape, brandy, rum, whiskey, sherry, red and white wines, Scotch and Canadian whiskey, pork (fried), cocoa, peanuts (raw), mushrooms, guava fruit, mangos (fresh), wort, vanilla and black chokeberries.

Uses

Vanillic acid is used as a flavoring agent in food. It acts as an intermediate in the production of vanillin from ferulic acid. Further, it is used in wine and vinegar.

Uses

Vanillin, a compound widely used in foods, beverages, cosmetics and drugs, has been reported to exhibit multifunctional effects such as antimutagenic, antiangiogenetic, anti-colitis, anti-sickling, an d antianalgesic effects. However, results of studies on the antioxidant activity of vanillin are not consistent.

Uses

A flavoring agent.

Definition

ChEBI: A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.

Preparation

Prepared by bioconversion of ferulic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BS13. Also prepared by whole-cell bioconversion of vanillin to vanillic acid by Streptomyces viridosporus

Aroma threshold values

Aroma at 5.0%: weak vanilla, creamy, milky.

Taste threshold values

Taste characteristics at 100 ppm: weak sweet resinous vanilla, creamy with a smooth sweetness and body, slightly chocolate-like with a spicy vanitrop nuance

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 429, 1946 DOI: 10.1021/ja01207a025
Organic Syntheses, Coll. Vol. 4, p. 972, 1963

General Description

Vanillic acid is one of the key aromatic volatile compounds of vanilla beans.

Biochem/physiol Actions

Taste at 100 ppm

Vanillic acid (121-34-6)Related Product Information

• Nonivamide
• CHLOROPHOSPHONAZO III
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• Homovanillic acid
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• 2,6-Dimethoxybenzoic acid
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• 4-Methoxybenzoic acid
• 4-Hydroxybenzoic acid
• VANILLIC ACID ETHYL ESTER,VANILLIC ACID ETHYL ESTER 97+%
• Methylparaben