alpha-Cyperone

Base Information

• Chemical Name: alpha-Cyperone
• CAS No.: 473-08-5
• Molecular Formula: C15H22O
• Molecular Weight: 218.339
• Hs Code.: 29143990
• UNII: ZL24SG1C2D
• DSSTox Substance ID: DTXSID60197086
• Nikkaji Number: J11.889C
• Wikidata: Q72461262
• Metabolomics Workbench ID: 125686
• ChEMBL ID: CHEMBL1939885
• Mol file: 473-08-5.mol

Synonyms:2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-1,4a-dimethyl-7-(1-methylethenyl)-, (4aS-cis)-;Eudesma-4,11-dien-3-one (7CI,8CI);a-Cyperone (6CI);(+)-a-Cyperone;a-Cyperone,(+)-;

Chemical Property of alpha-Cyperone

Chemical Property:

• Vapor Pressure: 0.000319mmHg at 25°C
• Melting Point: 232 °C
• Refractive Index: 1.503
• Boiling Point: 320.4 °C at 760 mmHg
• Flash Point: 142.8 °C
• PSA: 17.07000
• Density: 0.97 g/cm³
• LogP: 4.04830
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 375

Purity/Quality:

98% ^*data from raw suppliers

Alpha Cyperone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2CC(CCC2(CCC1=O)C)C(=C)C
• Isomeric SMILES: CC1=C2C[C@@H](CC[C@]2(CCC1=O)C)C(=C)C
• Uses: (+)-α-Cyperone is used as an anti-inflammatory agent, isolated from the rhizomes of Cyperus rotundus.

Technology Process of alpha-Cyperone

There total 33 articles about alpha-Cyperone 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: 82.0%

Imidazole-1-carbothioic acid O-((1S,3S,8aS)-3-isopropenyl-5,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl) ester (148706-53-0) → eudesma-4,11-dien-3-one (473-08-5)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; for 2h; Heating;

DOI:10.1016/S0957-4166(00)80168-8

Reference yield: 78.0%

<1S,4R>-1-methyl-1-(3-pentanone)-4-isopropenyl-2-oxocyclohexane (108032-82-2) → eudesma-4,11-dien-3-one (473-08-5)

Guidance literature:

With potassium hydroxide; In ethanol; at 25 ℃;

DOI:10.1016/S0040-4020(01)82058-5

Reference yield: 51.0%

α-cyperene (17627-30-4) → eudesma-4,11-dien-3-one (473-08-5)

Guidance literature:

With pyridine; tert.-butylhydroperoxide; N-hydroxy-3,4,5,6-tetrachlorophthalimide; lithium perchlorate; In acetone; chemoselective reaction; Electrochemical reaction;

DOI:10.1038/nature17431

upstream raw materials:

(2R,5R)-5-isopropenyl-2-methylcyclohexanone

4-penten-3-one

(R)-5-Isopropenyl-2-methyl-2-(3-oxo-pentyl)-cyclohexanone

<1S,4R>-1-methyl-1-(3-pentanone)-4-isopropenyl-2-oxocyclohexane

Downstream raw materials:

r-eudesmol

(+)-chrysanthemol

(2R,4aS,7R)-1,4a-dimethyl-7-(prop-1-en-2-yl)2,3,4,4a5,6,7,8-octahydronaphthalen-2-ol

β-rotunol

Refernces

• 1、 Agami, Claude,Kadouri-Puchot, Catherine,Guen, Valerie Le. "Synthesis of Homochiral α-Cyperone via Enantioselective Catalysis". . p. 641 - 644. Retrieved 1993.
• 2、 Park, Ju-Young,Shin, Young-Gyun,Kim, Kee-Won,Kwon, Young-Bae,Yoon, Sung-Hwa. "Syntheses of 7-substituted a-cyperone derivatives for selective sigma-1 receptor over cannabinoid-1 receptor binding affinities". . p. 3499 - 3502. Retrieved 2014/01/06.
• 3、 Xiong, Zhaoming,Yang, Jiong,Li, Yulin. "An efficient asymmetric route to eudesmane acids. Total synthesis of (+)-12-hydroxy-α-cyperone, (+)-12-oxo-α-cyperone and (+)-3-oxoeudesma-4,11(13)-dien-12-oic acid". . p. 2607 - 2612. Retrieved 2007/10/03.