473-08-5

Basic information

• Product Name: alpha-Cyperone
• Synonyms: α-cyperone;A-CYPERONE;(4aS,7R)-1,4a-Dimethyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one;(4aS-cis)-4,4a,5,6,7,8-Hexahydro-1,4a-dimethyl-7-(1-methylethenyl)-2(3H)-naphthalenone;alpha-Cyperone;2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-1,4a-;dimethyl-7-(1-methylethenyl)-,(4aS,7R)-;(4aS)-4,4a,5,6,7,8-Hexahydro-7β-isopropenyl-1,4aβ-dimethylnaphthalene-2(3H)-one
• CAS NO: 473-08-5
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.33
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 473-08-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 232 °C
• Boiling Point: 320.4 °C at 760 mmHg
• Flash Point: 142.8 °C
• Appearance: /
• Density: 0.97 g/cm³
• Vapor Pressure: 0.000319mmHg at 25°C
• Refractive Index: 1.503
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: alpha-Cyperone(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Cyperone(473-08-5)
• EPA Substance Registry System: alpha-Cyperone(473-08-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 473-08-5(Hazardous Substances Data)

Usage

Description

alpha-Cyperone, also known as (+)-α-Cyperone, is a natural compound derived from the rhizomes of Cyperus rotundus, a plant commonly found in various regions around the world. It possesses anti-inflammatory properties and has been the subject of research for its potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
alpha-Cyperone is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate pain. It is particularly useful in the treatment of conditions characterized by inflammation, such as arthritis and other musculoskeletal disorders.
Used in Traditional Medicine:
In addition to its modern pharmaceutical applications, alpha-Cyperone has been utilized in traditional medicine for centuries, particularly in the treatment of various inflammatory conditions. Its natural origin and proven efficacy make it a valuable component in the development of alternative and complementary therapies.
Used in Research and Development:
Due to its potent anti-inflammatory properties, alpha-Cyperone is also used as a subject of research and development in the pharmaceutical and biotechnology industries. Scientists are exploring its potential for the development of new drugs and therapies targeting inflammation-related diseases and conditions.

InChI:InChI=1/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3/t12-,15+/m1/s1

Upstream product

• 141871-26-3 (1'R,4'aS,7'S,8'aR)-7'-Isopropenyl-1',4'a-dimethyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-ol 
• 1629-58-9 4-penten-3-one 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 38043-97-9 1-Keto-α-cyperon 
• 20084-99-5 (2R,4aS,7R)-1,4a-dimethyl-7-(prop-1-en-2-yl)2,3,4,4a5,6,7,8-octahydronaphthalen-2-ol 
• 148706-53-0 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 
• 108032-82-2 <1S,4R>-1-methyl-1-(3-pentanone)-4-isopropenyl-2-oxocyclohexane 
• 192993-39-8 (R)-5-Isopropenyl-2-methyl-2-(3-oxo-pentyl)-cyclohexanone 
• 5524-05-0 (2R,5R)-5-isopropenyl-2-methylcyclohexanone 
• 17627-30-4 α-cyperene 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 1618-78-6 6-epi-α-Santonin 
• 18172-86-6 methyl (11S)-3-oxo-7αH-eudesma-1,4-dien-12-oate 
• 18172-87-7 methyl (11S)-3-oxo-eudesm-4-en-13-oate 

Downstream Products

• 23665-63-6 β-cyperone 
• 23665-82-9 eudesma-4,11-dien-3-one-(2,4-dinitro-phenylhydrazone) 
• 355010-41-2 (+)-α-cyperone tosylhydrazone 
• 68961-96-6 2β-(t-butyldimethylsilyloxy)eudesma-4,11-dien-3β-ol 
• 473-16-5 r-eudesmol 
• 113773-90-3 (+)-chrysanthemol 
• 104154-15-6 2-[(2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]acrylaldehyde 
• 28399-17-9 (+)-Eudesma-3,11⁽¹³⁾-dien-12-oic acid 
• 13902-07-3 eudesm-4-en-11-ol 
• 119765-86-5 11-hydroxy-4,5-seco-endesmane-4,5-dione 
• 77521-40-5 kudtriol 
• 473-13-2 α-selinene 
• 176776-01-5 (1R,4R,6R,8aR)-6-(1-Hydroxy-1-methyl-ethyl)-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol 
• 176665-72-8 2-[(2R,4aS,7R,8S)-4a,8-Dimethyl-7-(2-nitro-phenylselanyl)-2,3,4,4a,7,8-hexahydro-naphthalen-2-yl]-propan-2-ol 

Relevant articles and documents

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Scalable and sustainable electrochemical allylic C-H oxidation

New methods and strategies for the direct functionalization of C-H bonds are beginning to reshape the field of retrosynthetic analysis, affecting the synthesis of natural products, medicines and materials. The oxidation of allylic systems has played a prominent role in this context as possibly the most widely applied C-H functionalization, owing to the utility of enones and allylic alcohols as versatile intermediates, and their prevalence in natural and unnatural materials. Allylic oxidations have featured in hundreds of syntheses, including some natural product syntheses regarded as € classics €. Despite many attempts to improve the efficiency and practicality of this transformation, the majority of conditions still use highly toxic reagents (based around toxic elements such as chromium or selenium) or expensive catalysts (such as palladium or rhodium). These requirements are problematic in industrial settings; currently, no scalable and sustainable solution to allylic oxidation exists. This oxidation strategy is therefore rarely used for large-scale synthetic applications, limiting the adoption of this retrosynthetic strategy by industrial scientists. Here we describe an electrochemical C-H oxidation strategy that exhibits broad substrate scope, operational simplicity and high chemoselectivity. It uses inexpensive and readily available materials, and represents a scalable allylic C-H oxidation (demonstrated on 100 grams), enabling the adoption of this C-H oxidation strategy in large-scale industrial settings without substantial environmental impact.

Stereoselective total synthesis of (-)-α-eudesmol, a P/Q-type calcium channel blocker

Practical and stereoselective total synthesis of (-)-αeudesmol 1, a P/Q-type calcium channel blocker, has been achieved with the key step being a cyclopropane ring opening accompanying introduction of a hydroxyl group. (+)-Carissone is used as a key intermediate.

An efficient and stereoselective synthesis of (+)-α-cyperone

An efficient and stereoselective three step synthesis of (+)-α-cyperone 1 is described. The key step involves a stereoselective Michael addition of chiral imine to (R)-dihydrocarvone.