Methyl vanillate Chemical Properties

Melting point:

64-67 °C (lit.)

Boiling point:

285-287 °C (lit.)

Density 

1.2481 (rough estimate)

refractive index 

1.4500 (estimate)

Flash point:

285-287°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in chloroform and methanol.

form 

Powder and Granules

pka

8.36±0.18(Predicted)

color 

Pale yellow to beige

Odor

at 100.00 %. warm spicy vanilla guaiacol phenolic carnation

Odor Type

vanilla

biological source

synthetic

BRN 

1369113

InChIKey

BVWTXUYLKBHMOX-UHFFFAOYSA-N

LogP

2.231 (est)

CAS DataBase Reference

3943-74-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester(3943-74-6)

EPA Substance Registry System

Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester (3943-74-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

RTECS 

DH2430000

TSCA 

Yes

HS Code 

29189900

MSDS

• Language:English Provider:Methyl 4-hydroxy-3-methoxybenzoate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl vanillate Usage And Synthesis

Chemical Properties

pale yellow to beige powder and granules

Uses

Methyl vanillate is used to investigate the volatile compounds of heather honeys from Calluna vulgaris and Erica arborea.

Uses

Methyl Vanillate maintains antimicrobial properties due to the phenylpropanoid moiety in the structure.

Definition

ChEBI: Methyl vanillate is a benzoate ester that is the methyl ester of vanillic acid. It has a role as an antioxidant and a plant metabolite. It is a benzoate ester, a member of phenols and an aromatic ether. It is functionally related to a vanillic acid.

General Description

Methyl vanillate is a volatile compound present in cloudberries (Rubus Chamaemorus.). Methyl vanillate can be synthesized from vanillic acid. Methyl vanillate has been identified in foods such as cow's milk and beer.

Biological Activity

Methyl vanillate, one of the ingredients in Hovenia dulcis Thunb, is a Wnt/β-catenin pathway activator. A benzoate ester that is the methyl ester of vanillic acid. It has a role as an antioxidant and a plant metabolite.

References

[1] PU-HYEON CHA. Hovenia dulcis Thunb extract and its ingredient methyl vanillate activate Wnt/β-catenin pathway and increase bone mass in growing or ovariectomized mice.[J]. PLoS ONE, 2014: e85546. DOI:10.1371/journal.pone.0085546.
[2] ADRIANO DE SOUZA PESSOA . The dimerization of methyl vanillate improves its effect against breast cancer cells via pro-oxidant effect[J]. Chemico-Biological Interactions, 2022, 361: Article 109962. DOI:10.1016/j.cbi.2022.109962.
[3] CHRONG-SHYUA CHU  P. D R C Liao. A formal synthesis of (+/-)-reserpine from methyl vanillate[J]. Chemical Communications, 1996, 1 1: 1537-1538. DOI:10.1039/CC9960001537.
[4] JUAN TIAN. Ethyl acetate as a co-solvent and sacrificial ester in the aluminum triiodide promoted chemoselective demethylation of methyl vanillate[J]. Tetrahedron Letters, 2017, 58 36: Pages 3522-3524. DOI:10.1016/j.tetlet.2017.07.089.

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