Ethyl vanillate

Base Information

• Chemical Name: Ethyl vanillate
• CAS No.: 617-05-0
• Deprecated CAS: 1383616-21-4
• Molecular Formula: C10H12O4
• Molecular Weight: 196.203
• Hs Code.: 29189900
• European Community (EC) Number: 210-503-9
• NSC Number: 8513
• UNII: V38JK4Z93O
• DSSTox Substance ID: DTXSID2060670
• Nikkaji Number: J21.705K
• Wikidata: Q27291476
• ChEMBL ID: CHEMBL4206971
• Mol file: 617-05-0.mol

Synonyms:Ethyl vanillate;617-05-0;Ethyl 4-hydroxy-3-methoxybenzoate;4-Hydroxy-3-methoxybenzoic acid ethyl ester;VANILLIC ACID, ETHYL ESTER;Benzoic acid, 4-hydroxy-3-methoxy-, ethyl ester;3-Methoxy-4-hydroxybenzoic acid, ethyl ester;m-Anisic acid, 4-hydroxy-, ethyl ester;NSC 8513;EINECS 210-503-9;BRN 2100025;UNII-V38JK4Z93O;AI3-06151;V38JK4Z93O;CHEMBL4206971;NSC-8513;MFCD00017269;3-10-00-01413 (Beilstein Handbook Reference);ethylvanillate;Vanilicacidethylester;97%;ethyl 4-hydroxy-3-methoxy-benzoate;Vanillic acid ethyl;Vanilic acid ethyl ester;Caffeoyl Efhylesfer,(S);Vanillic Acid Ethyl Ester;m-Anisic acid, ethyl ester;WLN: 2OVR DQ CO1;SCHEMBL155638;DTXSID2060670;ethyl 4-hydoxy-3-methoxybenzoate;NSC8513;CHEBI:181310;ethyl 3-methoxy-4-hydroxybenzoate;HY-B1643;BDBM50450894;s3993;AKOS006227599;CCG-266551;AS-14750;ETHYL-4-HYDROXY-3-METHOXYBENZOATE;SY015808;LS-161396;CS-0013594;FT-0618640;V0051;Ethyl vanillate, analytical reference material;F14083;W-105106;Q27291476

Chemical Property of Ethyl vanillate

Chemical Property:

• Appearance/Colour: Burnt coffee odor.
• Melting Point: 43-45ºC
• Refractive Index: 1.5430 (estimate)
• Boiling Point: 292 ºCat 760 mmHg
• PKA: 8.36±0.18(Predicted)
• Flash Point: 122.4ºC
• PSA: 55.76000
• Density: 1.18 g/cm³
• LogP: 1.57750
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Ethyl vanillate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=C(C=C1)O)OC
• Uses: Food preservative, medicine, sunburn preventive.

Technology Process of Ethyl vanillate

There total 10 articles about Ethyl 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: 98.0%

ethanol (64-17-5) + 3-methoxy-4-hydroxybenzoic acid (121-34-6) → ethyl vanillate (617-05-0)

Guidance literature:

With sulfuric acid; for 48h; Inert atmosphere; Reflux;

Reference yield: 87.0%

3-methoxy-4-hydroxybenzoic acid (121-34-6) + Triethyl orthoacetate (78-39-7) → ethyl vanillate (617-05-0)

Guidance literature:

microwave irradiation;

DOI:10.1081/SCC-120005431

Reference yield: 80.0%

3-methoxy-4-hydroxybenzoic acid (121-34-6) → ethyl 4-hydroxy-3-methoxybenzoate (ethyl vanillate) + ethyl vanillate (617-05-0)

Guidance literature:

With sulfuric acid; sodium hydrogencarbonate; mercury; In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate;

upstream raw materials:

ethanol

3-methoxy-4-hydroxybenzoic acid

ethyl 2-methoxyphenyl carbonate

ethyl iodide

Downstream raw materials:

4-(2-bromo-ethoxy)-3-methoxy-benzoic acid ethyl ester

4-(2,3-epoxy-propoxy)-3-methoxy-benzoic acid ethyl ester

4-(2-Dimethylamino-ethoxy)-3-methoxy-benzoic acid ethyl ester

ethyl 4-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-3-methoxybenzoate

Refernces

• 1、 Dasan, Neethu,Babu,George, Shiny. "Molecular docking studies and synthesis of 3, 4-disubstituted triazoles as mycobacterium tuberculosis enoyl-acp reductase and CYP-51 inhibitors". . p. 85 - 91. Retrieved 2019/02/19.
• 2、 Lancefield, Christopher S.,Teunissen, Lucas W.,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.. "Iridium-catalysed primary alcohol oxidation and hydrogen shuttling for the depolymerisation of lignin". supporting information. p. 3214 - 3221. Retrieved 2018/07/31.