Vanillic acid

Vanillic acid Chemical Properties
Melting point 208-210 °C(lit.)
Boiling point 257.07°C (rough estimate)
density 1.3037 (rough estimate)
FEMA 3988 | 4-HYDROXY-3-METHOXYBENZOIC ACID
refractive index 1.5090 (estimate)
storage temp. Store below +30°C.
solubility Acetonitrile (Slightly), Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly)
pkapKa 4.53(H2O t = 25 c = 0.016–0.001) (Uncertain)
form Liquid
color Clear colorless to brown, may darken during storage
Odorat 100.00 %. dairy milky custard creamy powdery vanilla bean
Odor Typecreamy
Water Solubility Soluble in water, alcohol and ether.
Merck 14,9931
JECFA Number959
BRN 2208364
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyWKOLLVMJNQIZCI-UHFFFAOYSA-N
LogP1.30
CAS DataBase Reference121-34-6(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, 4-hydroxy-3-methoxy-(121-34-6)
EPA Substance Registry SystemVanillic 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 Information
ProviderLanguage
4-Hydroxy-3-methoxybenzoic acid English
SigmaAldrich English
ACROS English
ALFA English
Vanillic acid Usage And Synthesis
DescriptionVanillic 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.
Referenceshttps://en.wikipedia.org/wiki/Vanillic_acid
https://pubchem.ncbi.nlm.nih.gov/compound/Vanillic_acid#section=Top
Chemical Propertieswhite odourless crystals or powder
Chemical Properties4-Hydroxy-3-methoxybenzoic acid has a vanilla-like odor and taste.
OccurrenceReported 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.
UsesVanillin, 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.
UsesA flavoring agent.
UsesVanillic 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.
PreparationPrepared 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
DefinitionChEBI: A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.
Aroma threshold valuesAroma at 5.0%: weak vanilla, creamy, milky.
Taste threshold valuesTaste 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 DescriptionVanillic acid is one of the key aromatic volatile compounds of vanilla beans.
Biochem/physiol ActionsTaste at 100 ppm
VANILLIC ACID ETHYL ESTER,VANILLIC ACID ETHYL ESTER 97+% 3,4-Dimethoxybenzoic acid Methylparaben 2,6-Dimethoxybenzoic acid Hyaluronic acid 4-Hydroxybenzoic acid Salicylic acid Ethyl 2-(Chlorosulfonyl)acetate 2'-Hydroxy-3-phenylpropiophenone Ascoric Acid Stearic acid 3-Hydroxybenzoic acid Folic acid p-Anisic acid Homovanillic acid Nonivamide CHLOROPHOSPHONAZO III Citric acid

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