Anethole, (Z)-

Base Information

• Chemical Name: Anethole, (Z)-
• CAS No.: 25679-28-1
• Deprecated CAS: 7677-68-1
• Molecular Formula: C10H12 O
• Molecular Weight: 148.205
• Hs Code.: 2909309090
• European Community (EC) Number: 247-181-4
• UNII: 78AWK1V4GL
• DSSTox Substance ID: DTXSID4058651
• Nikkaji Number: J55.375A
• Wikidata: Q27147814
• Metabolomics Workbench ID: 44592
• ChEMBL ID: CHEMBL1468832
• Mol file: 25679-28-1.mol

Synonyms:cis-Anethole;25679-28-1;(Z)-Anethole;(Z)-1-Methoxy-4-(prop-1-en-1-yl)benzene;cis-p-Propenylanisole;cis-p-Anethole;Anethole, cis;(Z-)-Anethole;ANISOLE, p-PROPENYL-, cis-;Anethole, (Z)-;1-methoxy-4-[(Z)-prop-1-enyl]benzene;78AWK1V4GL;Benzene, 1-methoxy-4-(1-propenyl)-, (Z)-;ANETHOLE, CIS-;EINECS 247-181-4;UNII-78AWK1V4GL;BRN 1209632;cis-p-Methoxy-beta-methylstyrene;DTXSID4058651;CHEBI:78412;1-methoxy-4-[(1Z)-prop-1-en-1-yl]benzene;E-anethole;trans-Anise camphor;Methoxy-4-propenylbenzene;1-Methoxy-4-propenylbenzene;4-06-00-03796 (Beilstein Handbook Reference);trans-1-(p-Methoxyphenyl)propene;Anistearoptene;1-(4-Methoxyphenyl)-1(3)-propene;Anethole, USAN;NCGC00091493-01;4-cis-propenyl-anisole;p-Propenylanisole, 8CI;p-Propenyl-trans-Anisole;CIS-ANETHOLE [MI];SCHEMBL57011;ghl.PD_Mitscher_leg0.374;1-(p-Methoxyphenyl)-Propene;Anisole, p-propenyl-, (Z)-;CHEMBL1468832;DTXCID0032283;FEMA 2086;1-Methoxy-4-(propenyl)-Benzene;1-Methoxy-4-(propen-1-yl)-Benzene;AKOS015840488;Anisole, p-propenyl-, (E)- (8CI);1-Methoxy-4-(1E)-1-propenyl-Benzene;1-Methoxy-4-(1-propenyl)benzene, 9CI;1-Methoxy-4-(1-propenyl)-(E)-Benzene;LS-20221;1-Methoxy-4-(1E)-1-propen-1-yl-Benzene;methyl 4-[(1Z)-prop-1-en-1-yl]phenyl ether;Q27147814

Chemical Property of Anethole, (Z)-

Chemical Property:

• Vapor Pressure: 0.0687mmHg at 25°C
• Melting Point: -22.5°
• Refractive Index: nD20 1.55455
• Boiling Point: 237.5°Cat760mmHg
• Flash Point: 88.4°C
• PSA: 9.23000
• Density: 0.959g/cm³
• LogP: 2.72830
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 148.088815002
• Heavy Atom Count: 11
• Complexity: 121

Purity/Quality:

99% ^*data from raw suppliers

Cis-Anethole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=CC=C(C=C1)OC
• Isomeric SMILES: C/C=C\C1=CC=C(C=C1)OC
• Uses: Flavoring agent in foods and beverages; in perfumery, particularly for soap and dentifrices; pharmaceutic aid (flavor).

Technology Process of Anethole, (Z)-

There total 64 articles about Anethole, (Z)- 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: 15.0%

Estragole (140-67-0) → cis-Anethole (25679-28-1,25086-72-0,63589-56-0) + 4-n-propylanisole (104-45-0) + E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8,25086-72-0,63589-56-0)

Guidance literature:

With borane-ammonia complex; iron(II)β-diketiminate complex; In benzene-d6; at 60 ℃; for 16h; Overall yield = 62 percent; Overall yield = 45.9 mg; Optical yield = 80.769 percent de; Inert atmosphere; Glovebox;

DOI:10.1002/chem.202004980

Reference yield:

4-methoxy-benzaldehyde (123-11-5) + ethyl iodide (75-03-6) → cis-Anethole (25679-28-1,25086-72-0,63589-56-0) + E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8,25086-72-0,63589-56-0)

Guidance literature:

With 1-(3,5-bis(trifluoromethyl)phenyl)phospholane-1-oxide; diphenylsilane; sodium t-butyl carbonate; In toluene; at 150 ℃; for 48h; Reagent/catalyst; Temperature; Overall yield = 63 %; Overall yield = 94 mg; Schlenk technique; Sealed tube; Inert atmosphere;

Reference yield:

Estragole (140-67-0) → cis-Anethole (25679-28-1,25086-72-0,63589-56-0) + E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8,25086-72-0,63589-56-0)

Guidance literature:

With tricarbonylbis(triphenylphosphine)ruthenium⁽⁰⁾; magnesium triflate; In ethanol; at 80 ℃; for 0.5h; Reagent/catalyst;

DOI:10.1002/cctc.201700687

upstream raw materials:

Estragole

6-methylphenanthridine

E-1-(4'-methoxyphenyl)prop-1-ene

1-methoxy-4-(prop-1-yn-1-yl)benzene

Downstream raw materials:

2-acetoxymercurio-1-(4-methoxyphenyl)-1-methoxypropane

(+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylbenzofuran

Z-1-(2-chloroethenyl)phenyl methyl ether

1-[(E)-2-chlorovinyl]-4-methoxybenzene

Refernces

• 1、 Kim, Daniel,Pillon, Guy,Diprimio, Daniel J.,Holland, Patrick L.. "Highly Z-Selective Double Bond Transposition in Simple Alkenes and Allylarenes through a Spin-Accelerated Allyl Mechanism". supporting information. p. 3070 - 3074. Retrieved 2021/03/08.
• 2、 Huang, Zhidao,Wang, Yulei,Leng, Xuebing,Huang, Zheng. "An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne cis-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis". supporting information. p. 4824 - 4836. Retrieved 2021/04/07.