Ethyl homovanillate

Base Information

• Chemical Name: Ethyl homovanillate
• CAS No.: 60563-13-5
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• Hs Code.: 29189900
• European Community (EC) Number: 262-298-0
• UNII: K3SBN6E2A9
• DSSTox Substance ID: DTXSID30209367
• Nikkaji Number: J236.364J
• Wikidata: Q83083640
• ChEMBL ID: CHEMBL3747410
• Mol file: 60563-13-5.mol

Synonyms:Ethyl homovanillate;60563-13-5;ethyl 2-(4-hydroxy-3-methoxyphenyl)acetate;Ethyl 4-hydroxy-3-methoxyphenylacetate;4-HYDROXY-3-METHOXYPHENYLACETIC ACID ETHYL ESTER;Benzeneacetic acid, 4-hydroxy-3-methoxy-, ethyl ester;K3SBN6E2A9;EINECS 262-298-0;MFCD00009180;ethyl-2-(4-hydroxy-3-methoxyphenyl)acetate;Ethyl homovanillate, 97%;UNII-K3SBN6E2A9;(4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester;SCHEMBL2002022;CHEMBL3747410;FEMA NO. 4810;AWPMWZHWVKXADV-UHFFFAOYSA-;DTXSID30209367;AKOS005259451;ethyl 3-methoxy-4-hydroxy-phenylacetate;Ethyl 4-hydroxy-3-methoxyphenyl acetate;ethyl(4-hydroxy-3-methoxyphenyl)acetate;DS-14492;ethyl (4-hydroxy-3-methoxyphenyl)acetate;FT-0640701;ethyl [4-hydroxy-3-(methyloxy)phenyl]acetate;E75840;3-methoxy-4-hydroxybenzeneacetic acid ethyl ester;A832782;Benzeneacetic acid,4-hydroxy-3-methoxy-,ethyl ester

Chemical Property of Ethyl homovanillate

Chemical Property:

• Appearance/Colour: White to pale yellowish crystalline powder
• Vapor Pressure: 0.000253mmHg at 25°C
• Melting Point: 44-47 °C
• Refractive Index: 1.523
• Boiling Point: 314.4 °C at 760 mmHg
• PKA: 9.88±0.20(Predicted)
• Flash Point: 121.6 °C
• PSA: 55.76000
• Density: 1.16 g/cm³
• LogP: 1.50640
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl homovanillate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC1=CC(=C(C=C1)O)OC

Technology Process of Ethyl homovanillate

There total 6 articles about Ethyl homovanillate 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: 99.0%

ethanol (64-17-5) + Homovanillic acid (306-08-1) → ethyl homovanillate (60563-13-5)

Guidance literature:

With sulfuric acid; for 2h; Reflux;

DOI:10.1016/j.bmc.2010.09.001

Reference yield: 91.0%

ethanol (64-17-5) + 4-hydroxy-3-methoxy-mandelic acid (55-10-7,2394-20-9) → ethyl homovanillate (60563-13-5)

Guidance literature:

With phosphonic Acid; methanesulfonic acid; sodium iodide; at 80 ℃; for 4h; Reagent/catalyst;

Reference yield:

2-methoxy-phenol (90-05-1) → ethyl homovanillate (60563-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water / 20 °C / Cooling with ice

2: tin(ll) chloride; hydrogenchloride / water / 4 h / 80 °C

3: sulfuric acid / 2 h / Reflux

With hydrogenchloride; sulfuric acid; tin(ll) chloride; sodium hydroxide; In water;

upstream raw materials:

ethanol

Homovanillic acid

2-methoxy-phenol

4-hydroxy-3-methoxy-mandelic acid

Downstream raw materials:

ethyl (3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate

2-(4-hydroxy-3-methoxyphenyl)ethyl acetate

(3-bromo-4-hydroxy-5-methoxyphenyl)acetic acid ethyl ester

(3-methoxy-4-methoxymethoxyphenyl)acetic acid ethyl ester

Refernces

• 1、 -. "HOMOVANILLIC ESTER, MORE PARTICULARLY FOR ACHIEVING AN IMPRESSION OF HEAT AND/OR SPICINESS". Paragraph 0195; 0196; 0217-0220. . Retrieved 2019/09/20.
• 2、 Lieder, Barbara,Hans, Joachim,Hentschel, Fabia,Geissler, Katrin,Ley, Jakob. "Biological evaluation of natural and synthesized homovanillic acid esters as inhibitors of intestinal fatty acid uptake in differentiated Caco-2 cells". . . Retrieved 2019/10/14.