Methyl vanillate

Base Information

• Chemical Name: Methyl vanillate
• CAS No.: 3943-74-6
• Deprecated CAS: 1220026-96-9
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 29189900
• European Community (EC) Number: 223-525-9
• NSC Number: 74385
• UNII: 2HXG8QSO3D
• DSSTox Substance ID: DTXSID5074345
• Nikkaji Number: J45.025A
• Wikidata: Q27097897
• Metabolomics Workbench ID: 56659
• ChEMBL ID: CHEMBL486214
• Mol file: 3943-74-6.mol

Synonyms:methyl vanillate

Chemical Property of Methyl vanillate

Chemical Property:

• Appearance/Colour: pale yellow to beige powder and granules
• Vapor Pressure: 0.00157mmHg at 25°C
• Melting Point: 64-67 °C(lit.)
• Refractive Index: 1.534
• Boiling Point: 286 °C at 760 mmHg
• PKA: 8.36±0.18(Predicted)
• Flash Point: 120.2 °C
• PSA: 55.76000
• Density: 1.216 g/cm³
• LogP: 1.18740
• Storage Temp.: Room temperature.
• Solubility.: Soluble in chloroform and methanol.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

98%min ^*data from raw suppliers

Methyl Vanillate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C(=O)OC)O
• Uses: Methyl Vanillate maintains antimicrobial properties due to the phenylpropanoid moiety in the structure. Methyl vanillate is used to investigate the volatile compounds of heather honeys from Calluna vulgaris and Erica arborea. Methyl vanillate was used to investigate the volatile compounds of heather honeys from Calluna vulgaris and Erica arborea.

Technology Process of Methyl vanillate

There total 28 articles about Methyl vanillate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + 3-methoxy-4-hydroxybenzoic acid (121-34-6) → 4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6)

Guidance literature:

With hydrogenchloride; for 12h; Reflux;

Reference yield: 95.0%

methyl 4-(benzyloxy)-3-methoxybenzoate (56441-97-5) → 4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In various solvent(s); at 20 ℃; for 6h; under 760 Torr;

DOI:10.1055/s-2003-45007

Reference yield: 94.0%

methanol (67-56-1) + vanillin (121-33-5,8014-42-4) → 4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6)

Guidance literature:

With perchloric acid; sodium percarbonate; vanadia; for 2h; Cooling;

DOI:10.1021/jo0266902

upstream raw materials:

methanol

3-methoxy-4-hydroxybenzoic acid

diazomethane

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Downstream raw materials:

methyl 4-(benzyloxy)-3-methoxybenzoate

4-benzoyloxy-3-methoxy-benzoic acid methyl ester

3,3'-dimethoxy-4,4'-p-xylylenedioxy-di-benzoic acid dimethyl ester

4-Hexyloxy-3-methoxy-benzoic acid methyl ester

Refernces

• 1、 Wang, Kai,Zhang, Xiu-Qin,Zhu, Jian,Chen, Qiang,Zhang, Zhong-Qiang,Fan, Li. "Synthesis, characterization and crystal structure of methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate". . p. 2647 - 2650. Retrieved 2015.
• 2、 -. "VISUAL DETECTION OF PBD INDUCED DNA CROSSLINKS". Page/Page column 37; 38. . Retrieved 2021/04/23.
• 3、 Ruyet, Louise,Poisson, Thomas,Besset, Tatiana. "Transition Metal-Free Regioselective Remote C?H Bond 2,2,2-Trifluoroethoxylation of 8-Aminoquinoline Derivatives at the C5 Position". supporting information. p. 3407 - 3410. Retrieved 2021/06/28.