gamma-Asarone

Base Information

• Chemical Name: gamma-Asarone
• CAS No.: 5353-15-1
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• Hs Code.: 2909309090
• UNII: D4G4B8R48N
• DSSTox Substance ID: DTXSID10201743
• Nikkaji Number: J391.784C
• Wikidata: Q27155291
• Metabolomics Workbench ID: 44094
• Mol file: 5353-15-1.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 gamma-Asarone

Chemical Property:

• Vapor Pressure: 0.00424mmHg at 25°C
• Melting Point: 25 °C
• Boiling Point: 287.7°Cat760mmHg
• Flash Point: 95.4°C
• PSA: 27.69000
• Density: 1.011g/cm³
• LogP: 2.44090
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 193

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1CC=C)OC)OC

Technology Process of gamma-Asarone

There total 12 articles about gamma-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: 87.0%

1,2,4-trimethoxy-benzene (135-77-3) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Guidance literature:

With carbon monoxide; In nitromethane; at 25 ℃; for 20h; under 760 Torr;

DOI:10.1016/S0040-4039(00)96742-X

Reference yield: 60.0%

methylallylether (627-40-7) + C9H11F3O5SSi → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Guidance literature:

With cesium fluoride; In tetrahydrofuran; at 50 ℃; for 28h; Inert atmosphere;

DOI:10.1002/ejoc.202001499

Reference yield: 43.0%

2,4,5-trimethoxycinnamyltosylhydrazone (437761-99-4) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Guidance literature:

With sodium tetrahydroborate; In acetic acid; at 90 - 120 ℃; for 12h;

DOI:10.1021/np010559s

upstream raw materials:

methanol

1,2-dimethoxy-4-(2-propenyl)benzene

3,4-dimethoxyphenol

allyl bromide

Downstream raw materials:

asaraldehyde

trans 2,4,5-trimethoxy cinnamaldehyde

2-(2,4,5-trimethoxyphenyl)acetaldehyde

1-propyl-2,4,5-trimethoxybenzene

Refernces

• 1、 Zhang, Jian,Mu, Keman,Yang, Peng,Feng, Xinqian,Zhang, Di,Fan, Xiangyu,Wang, Qiantao,Mao, Shengjun. "Synthesis, antiepileptic effects, and structure-activity relationships of α-asarone derivatives: In vitro and in vivo neuroprotective effect of selected derivatives". . . Retrieved 2021/08/03.
• 2、 Schuch, Dominik,Fries, Patrick,Doenges, Maike,Perez, Barbara Menendez,Hartung, Jens. "Reductive and brominative termination of alkenol cyclization in aerobic cobalt-catalyzed reactions". supporting information; experimental part. p. 12918 - 12920. Retrieved 2009/12/05.