Anethole

Base Information

• Chemical Name: Anethole
• CAS No.: 4180-23-8
• Deprecated CAS: 12002-40-3,8022-08-0,109957-71-3,57131-42-7
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• Hs Code.: 29093090
• European Community (EC) Number: 224-052-0,288-194-5,256-753-2,203-205-5
• NSC Number: 758626,209529,4018
• UN Number: 1993
• UNII: Q3JEK5DO4K
• DSSTox Substance ID: DTXSID9020087
• Nikkaji Number: J4.026F,J61.645A
• Wikipedia: Anethole
• Wikidata: Q255564
• NCI Thesaurus Code: C76862
• RXCUI: 17881
• Metabolomics Workbench ID: 55161
• ChEMBL ID: CHEMBL452630
• Mol file: 4180-23-8.mol

Synonyms:1-(4-methoxyphenyl)propene;1-methoxy-4-(1-propenyl)benzene;anethole;anethole, (E)-isomer;anethole, (Z)-isomer;p-propenylanisole;trans-anethole

Chemical Property of Anethole

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 1.33 hPa (63 °C)
• Melting Point: 20-21 °C(lit.)
• Refractive Index: n20/D 1.561(lit.)
• Boiling Point: 237.5 °C at 760 mmHg
• Flash Point: 88.4 °C
• PSA: 9.23000
• Density: 0.959 g/cm³
• LogP: 2.72830
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in benzene, ethyl acetate, acetone, carbon disulfide.
• Water Solubility.: practically insoluble
• 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
• Transport DOT Label: Combustible Liquid

Purity/Quality:

99% ^*data from raw suppliers

Anethole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N
• Statements: 43-51/53
• Safety Statements: 36/37-61

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: CC=CC1=CC=C(C=C1)OC
• Isomeric SMILES: C/C=C/C1=CC=C(C=C1)OC
• Description: (E)-Anethol is a phenylpropanoid that has been found in P. anisum seed oil and has antifungal and antioxidant activity. It is active against fermentatively growing S. cerevisiae under hypoxic, but not normoxic, conditions (MIC = 100 μg/ml), and against C. parapsilosis when used at a concentration of 15% w/w. (E)-Anethol has antioxidant activity in a Trolox equivalent antioxidant capacity (TEAC) assay but does not scavenge 2,2-diphenyl-1-picrylhydrazel (DPPH) radicals in a cell-free assay.
• Uses: flavoring agent in food, dentifrices, etc.; in perfumery for soap, etc.; in pharmaceuticals as flavor; in photography and in embedding materials in microscopy; some perfumery uses (fennei; absinthe; Hyacinth jacinthe; detergents; magnolia). Natural occurrence: star anise platelet aggregation inhibitor trans-Anethole is used to inhibits lung and forestomach carcinogenesis, used as carbon and energy supplement in the culture media of Pseudomonas putida strain. It is also used as used as a flavoring substance.

Technology Process of Anethole

There total 126 articles about Anethole 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%

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

Guidance literature:

With Polystyrene-supported 4-tert-butyl-2-(diisopropylphosphino)-1H-imidazole and ruthenium complex; In [⁽²⁾H₆]acetone; at 25 ℃; for 0.166667h; Reagent/catalyst; stereoselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/ol500327k

Reference yield: 99.0%

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:

cis-Anethole; 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; Reagent/catalyst; diastereoselective reaction; Catalytic behavior; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00072

Reference yield: 97.0%

1-bromo-4-methoxy-benzene (104-92-7) + potassium trifluoro(prop-1-en-2-yl)borate → E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8,25086-72-0,63589-56-0)

Guidance literature:

With potassium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In water; isopropyl alcohol; at 120 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

upstream raw materials:

Estragole

4-(3-chloro-allyl)-anisole

ethylmagnesium iodide

4-methoxy-benzaldehyde

Downstream raw materials:

p-methoxy-α-methylcinnamaldehyde

(E)-1-(4-hydroxyphenyl)propene

4-Propenyl-phenol

1-(4-methoxybenzylidene)-2-(4-nitrophenyl)hydrazine

Refernces

• 1、 Horky, Filip,Císa?ová, Ivana,?těpni?ka, Petr. "Synthesis, Reactivity, and Coordination of Semihomologous dppf Congeners Bearing Primary Phosphine and Primary Phosphine Oxide Groups". . p. 427 - 441. Retrieved 2021/02/06.
• 2、 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.