alpha-Asarone

Base Information

• Chemical Name: alpha-Asarone
• CAS No.: 2883-98-9
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• Hs Code.: 29093090
• European Community (EC) Number: 207-788-7,220-743-6
• NSC Number: 107257
• UNII: DQY9PNE5FK
• DSSTox Substance ID: DTXSID00871878
• Nikkaji Number: J7.927H,J70.975A
• Wikipedia: Asarone
• Wikidata: Q419658
• Pharos Ligand ID: NRS8FK5NYLJ2
• Metabolomics Workbench ID: 44897
• ChEMBL ID: CHEMBL333306
• Mol file: 2883-98-9.mol

Synonyms:(E)-asarone;(Z)-asarone;1,2,4-trimethoxy-5-propenylbenzene, z-;2,4,5-trimethoxypropen-1-ylbenzene;alpha-asarone;asarone;asarone, (E)-isomer;asarone, (Z)-isomer;benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (E)-;benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (Z)-;benzene, 1,2,4-trimethoxy-5-(1E)-1-propen-1-yl-;beta-asarone;cis-beta-asarone;cis-isoasarone;cis-isoelemicin;gamma-asarone;isoasarone;trans-asarone

Chemical Property of alpha-Asarone

Chemical Property:

• Appearance/Colour: monoclinic needles from water
• Vapor Pressure: 0.0026mmHg at 25°C
• Melting Point: 57-61 °C(lit.)
• Refractive Index: 1.526
• Boiling Point: 296 °C at 760 mmHg
• Flash Point: 107.7 °C
• PSA: 27.69000
• Density: 1.028 g/cm³
• LogP: 2.74550
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in chloroform, methanol.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 203

Purity/Quality:

97% ^*data from raw suppliers

trans-α-Asarone ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Other Insecticides
• Canonical SMILES: CC=CC1=CC(=C(C=C1OC)OC)OC
• Isomeric SMILES: C/C=C/C1=CC(=C(C=C1OC)OC)OC
• Uses: α-Asarone was used in the synthesis of series of α-asarone isomers and were investigated for their hypolipidemic and antiplatelet activities. α-Asarone was used in the synthesis of series of α-asarone isomers and were investigated for their hypolipidemic and antiplatelet activities. It is used in the synthesis of anti-inflammatory neolignan. Also used in lignan syntheses for antiallergic agents. It is clinically used as medication for treating epilepsy, cough, bronchitis and asthma. It exhibits neuroprotective, anti-oxidative, anticonvulsive and cognitive enhancing action.

Technology Process of alpha-Asarone

There total 45 articles about alpha-Asarone 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%

C12H16O3 (5273-86-9) → α-asarone (2883-98-9)

Guidance literature:

C₁₂H₁₆O₃; With cobalt(II) chloride; 2,2'-bis(diphenylphosphino)diphenylamine; In toluene; at 20 ℃; for 0.0833333h; Schlenk technique; Inert atmosphere;

With sodium triethylborohydride; In toluene; at 20 ℃; for 1h; diastereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00072

Reference yield: 97.0%

(E)-1-bromo-4,5-dimethoxy-2-(prop-1-en-1-yl)benzene (65720-03-8) + sodium methylate (124-41-4) → α-asarone (2883-98-9)

Guidance literature:

With copper(I) bromide; In N,N-dimethyl-formamide; for 18h; Reflux;

DOI:10.1080/00304948.2012.715061

Reference yield: 95.0%

1-(2,4,5-Trimethoxyphenyl)propan-1-ol (29652-82-2) → α-asarone (2883-98-9)

Guidance literature:

With sodium acetate; acetic anhydride; for 3h; Heating;

upstream raw materials:

C₁₂H₁₆O₃

dimethyl sulfate

3-Hydroxy-2-methyl-3-(2,4,5-trimethoxy-phenyl)-propionic acid

1-allyl-2,4,5-trimethoxybenzene

Downstream raw materials:

γ-diasarone

1-(2,4,5-Trimethoxyphenyl)-1,2-dihydroxypropane

C₁₂H₁₆O₃

asaraldehyde