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
• General Description: (Z)-Anethole, also known as cis-anethole, is a stereoisomer of anethole characterized by its cis-configuration around the double bond. It undergoes photoinduced electron transfer reactions, leading to isomerization, dimerization, and oxygenation when irradiated in the presence of electron acceptors. The isomerization occurs via triplet-state formation, while dimerization proceeds through a quasi-concerted cycloaddition of cation radicals, yielding cyclobutane dimers. Oxygen inhibits these processes, instead promoting the formation of oxygenated derivatives like p-anisaldehyde. Notably, the study rules out the involvement of an acyclic 1,4-cation radical in these reactions.

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

(4R*,5R*)-(+/-)-4,5-Dihydro-5-(4-methoxyphenyl)-4-methyl-3-isoxazolcarbonsaeure-ethylester

(4S*,5R*)-(+/-)-4,5-Dihydro-5-(4-methoxyphenyl)-4-methyl-3-isoxazolcarbonsaeure-ethylester

2-(1-(4-methoxyphenyl)propyl)-1-methyl-1H-indole-3-carbaldehyde

Refernces

Electron Transfer Induced Photoisomerization, Dimerization, and Oxygenation of trans- and cis-Anethole. The Role of Monomer and Dimer Cation Radicals

10.1021/ja00234a014

The study investigates the photoinduced electron transfer reactions of trans-anethole (t-A) and cis-anethole (c-A), focusing on their isomerization, dimerization, and oxygenation processes. When irradiated in the presence of electron acceptors like 9-cyanoanthracene (CA) or 9,10-dicyanoanthracene (DCA), both t-A and c-A undergo trans,cis isomerization and dimerization to form various cyclobutane dimers, with the dimer ratio being sensitive to reaction conditions. The presence of oxygen quenches isomerization and dimerization, leading to the formation of oxygenated products like p-anisaldehyde. The study concludes that isomerization occurs via reverse electron transfer to generate triplet anethole, while dimerization proceeds via quasi-concerted [2 + 1] cycloaddition of cation radicals. The results also suggest that an acyclic 1,4-cation radical is not involved in these reactions, as no [2 + 4] dimers or 1,2-dioxanes are detected.

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