Homovanillyl alcohol

Base Information

• Chemical Name: Homovanillyl alcohol
• CAS No.: 2380-78-1
• Molecular Formula: C9H12O3
• Molecular Weight: 168.192
• Hs Code.: 2909499000
• European Community (EC) Number: 219-175-1
• UNII: 9A7EE8MS6A
• DSSTox Substance ID: DTXSID40178494
• Nikkaji Number: J172D
• Wikipedia: Homovanillyl_alcohol
• Wikidata: Q5891855
• Metabolomics Workbench ID: 48372
• ChEMBL ID: CHEMBL3747068
• Mol file: 2380-78-1.mol

Synonyms:3 Methoxy 4 hydroxyphenylethanol;3-Methoxy-4-hydroxyphenylethanol;Alcohol, Hydroxymethoxyphenethyl;Hydroxymethoxyphenethyl Alcohol;Methoxyhydroxyphenylethanol;MHPE;MOPET

Chemical Property of Homovanillyl alcohol

Chemical Property:

• Appearance/Colour: yellow to light brown crystalline chunks
• Vapor Pressure: 0.000169mmHg at 25°C
• Melting Point: 40-42 °C(lit.)
• Refractive Index: 1.558
• Boiling Point: 316.8 °C at 760 mmHg
• PKA: 10.23±0.18(Predicted)
• Flash Point: 145.4 °C
• PSA: 49.69000
• Density: 1.182 g/cm³
• LogP: 0.93560
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 168.078644241
• Heavy Atom Count: 12
• Complexity: 127

Purity/Quality:

98%, ^*data from raw suppliers

Vanillylmethanol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CCO)O
• Uses: Homovanillyl alcohol is a biological metabolite of Hydroxytyrosol. Hydroxytyrosol is a phenolic compound that is present in virgin olive oil (VOO) and wine. Homovanillyl alcohol protects red blood cells (RBCs) from oxidative injury and has protective effect on cardiovascular disease. It was used in the preparation of galactosides.

Technology Process of Homovanillyl alcohol

There total 37 articles about Homovanillyl alcohol 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%

4-allylguaiacol (97-53-0) → homovanillyl alcohol (2380-78-1)

Guidance literature:

4-allylguaiacol; With ozone; In ethanol; at -55 ℃;

With sodium tetrahydroborate; In ethyl acetate; at 20 ℃;

Reference yield: 98.0%

tert-butyl 4-(2-tert-butoxyethyl)-2-methoxyphenyl carbonate → homovanillyl alcohol (2380-78-1)

Guidance literature:

With erbium(III) triflate; In ethanol; for 50h; Microwave irradiation;

DOI:10.1039/c0gc00728e

Reference yield: 97.3%

sodium methylate (124-41-4) + 3-bromo-4-hydroxyphenylethyl alcohol (196081-78-4) → homovanillyl alcohol (2380-78-1)

Guidance literature:

With copper(I) bromide; In N,N-dimethyl-formamide; at 120 ℃; for 1h;

DOI:10.1080/00397910701575509

upstream raw materials:

methanol

cistanoside C

cistanoside D

1-<4-(benzyloxy)-3-methoxyphenyl>ethan-2-ol

Downstream raw materials:

3-Methoxy-4-hydroxyphenylaethanol(TMS)2

1-<4-(benzyloxy)-3-methoxyphenyl>ethan-2-ol

4-(2-acetoxyethyl)-2-methoxy-1-acetoxy-benzene

2-(4'-hydroxy-3'-methoxyphenyl)ethyl methyl carbonate

Refernces

• 1、 Pepper,Steck. "". . p. 2867,2874. Retrieved 1963.
• 2、 Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi. "Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates". . p. 838 - 847. Retrieved 2021/02/09.