4176-01-6

Basic information

• Product Name: [1R-(1alpha,4beta,6beta)]-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one
• Synonyms: [1R-(1alpha,4beta,6beta)]-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one;(1R,4R,6S)-4α,7,7-Trimethylbicyclo[4.1.0]heptane-3-one;(1R,6S)-4α,7,7-Trimethylbicyclo[4.1.0]heptan-3-one;(1R,6β)-4α,7,7-Trimethylbicyclo[4.1.0]heptane-3-one;Einecs 224-042-6
• CAS NO: 4176-01-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 224-042-6
• Mol File: 4176-01-6.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 208.5°C at 760 mmHg
• Flash Point: 72.8°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 0.213mmHg at 25°C
• Refractive Index: 1.467
• CAS DataBase Reference: [1R-(1alpha,4beta,6beta)]-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: [1R-(1alpha,4beta,6beta)]-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one(4176-01-6)
• EPA Substance Registry System: [1R-(1alpha,4beta,6beta)]-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one(4176-01-6)

Safety Data

• Hazardous Substances Data: 4176-01-6(Hazardous Substances Data)

Usage

Description

[1R-(1α,4β,6β)]-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one, also known as α-himachalene, is a natural organic compound belonging to the class of bicyclic sesquiterpenoids. It is characterized by its unique and highly stable structure, featuring a bicyclic ring system with three methyl groups attached. [1R-(1alpha,4beta,6beta)]-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one is found in a variety of plant species, including conifers and herbs, and is responsible for their characteristic woody and pine-like aromas.

Uses

Used in Pharmaceutical Applications:
α-Himachalene is used as a potential therapeutic agent for various medicinal applications due to its pharmacological properties. These properties include anti-inflammatory, antioxidant, and antimicrobial effects, which make it a promising candidate for the development of new drugs and treatments.
Used in Aromatherapy:
In the aromatherapy industry, α-himachalene is used as a natural aroma compound for its characteristic woody and pine-like scents. It can be used in the formulation of essential oils and fragrances, providing a pleasant and calming sensory experience.
Used in Cosmetics:
[1R-(1alpha,4beta,6beta)]-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one can also be utilized in the cosmetics industry, where its unique scent and potential anti-inflammatory properties can be harnessed for the development of skincare and personal care products.
Used in Flavor and Fragrance Industry:
α-Himachalene can be employed in the flavor and fragrance industry to create natural and distinctive scents for various products, such as perfumes, candles, and air fresheners, capitalizing on its woody and pine-like aromas.

InChI:InChI=1/C10H16O/c1-6-4-7-8(5-9(6)11)10(7,2)3/h6-8H,4-5H2,1-3H3/t6-,7+,8-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 10395-49-0 (1S,4R,6R)-4-Methoxy-4,7,7-trimethyl-bicyclo[4.1.0]heptan-3-one 
• 13466-78-9 3-carene 
• 10395-49-0 (1S,4S,6R)-4-Methoxy-4,7,7-trimethyl-bicyclo[4.1.0]heptan-3-one 
• 4017-88-3 cis-carane-4-ol 
• 4017-88-3 (+/-)-cis-caran-trans-4-ol 
• 936-91-4 α-3,4-Epoxycarane 
• 141-52-6 sodium ethanolate 
• 4176-04-9 (1R,4S,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one 
• 4017-88-3 (+)-cis-caran-cis-4-ol 
• 4017-88-3 4-isocaranol 
• 936-91-4 3-carene epoxide 
• 67-56-1 methanol 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 

Downstream Products

• 4176-04-9 (1R,4S,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one 
• 4017-88-3 (+)-cis-caran-cis-4-ol 
• 4017-88-3 4-isocaranol 
• 4176-02-7 (-)-cis-Caran-3-on-semicarbazon 
• 4176-01-6 trans-4-caranone 
• 130467-35-5 (+)-trans-caran-cis-4-methanol 
• 4175-97-7 4-nitro-benzoic acid-((1S,3R,4R)-caran-4-yl ester) 
• 5208-43-5 (1R,3R,4R,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl 4-methylbenzenesulfonate 
• 6617-28-3 phthalic acid mono-((1S,3R,4R)-caran-4-yl ester) 
• 4175-97-7 4-nitro-benzoic acid-((1S,3R,4S)-caran-4-yl ester) 
• 5208-43-5 toluene-4-sulfonic acid-((1S,3R,4S)-caran-4-yl ester) 
• 6617-28-3 phthalic acid mono-((1S,3R,4S)-caran-4-yl ester) 
• 6909-21-3 (-)-cis-Caran-trans-(5)-ol 
• 5208-49-1 cis-4-carene 

Relevant articles and documents

Chemical and microbiological oxidation of (-)-cis-carane-4-one leading to chiral compounds and evaluation of their antifeedant activity

Starting from (+)-3-carene 1, naturally occurring bicyclic, monoterpene hydrocarbon, (-)-cis- carane-4-one 3 was obtained as a result of the two-step synthesis. Our investigations were focused on the optimization of chemical Baeyer-Villiger reaction of 3 leading to a-lactones. A mixture of terpenoid lactones 4a, 4b was obtained and next separated using column chromatography. The pure compounds were subjected to the evaluation of antifeedant activity towards three species of storage insects. Fusarium culmorum, Fusarium oxysporum and Aspergillus niger were chosen among six fungal strains to perform microbiological Baeyer- Villiger oxidation. As a result, three derivatives were isolated and characterized by spectroscopic methods. ARKAT-USA, Inc.

Reactions of cis-and trans-epoxy derivatives of (+)-3-carene and limonene with aldehydes over askanite-bentonite clay

cis-and trans-Epoxy derivatives of (+)-3-carene, limonene, and dipentene react with aldehydes in the presence of askanite-bentonite clay to give acetals. Hydrolysis of the latter selectively yields the corresponding cis-diols. The relative contribution of intra-and intermolecular processes in the reactions of epoxy derivatives with aldehydes is determined mainly by steric factor. * This study was financially supported by the Russian Foundation for Basic Research (project no. 97-03-32 952a).

Catalytic transformations of 3-carene oxide over alumina-rare earth oxide catalysts

Isomerization of 3-carene oxide over binary oxide catalysts like Al2O3-Y2O3, Al2O3-Sm2O3, Al2O3-Eu2O3, Al2O3-Pr6O11 and Al2O3-Nd2O3 at 80 deg C and 110 deg C has been studied. 3,6,6-Trimethylbicyclohexane-3-carboxaldehyde and caranone are the major products formed at 80 deg C.Rise in reaction temperature results in an increase in epoxide transformation and an irregular variation in the yield of products.