4176-01-6

Usage

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

• 10395-49-0 (1S,4S,6R)-4-Methoxy-4,7,7-trimethyl-bicyclo[4.1.0]heptan-3-one 
• 10395-49-0 (1S,4R,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 
• 13466-78-9 3-carene 
• 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 
• 67-63-0 isopropyl alcohol 
• 22339-03-3 3(10)-caren-4β-ol 

Downstream Products

• 4176-01-6 trans-4-caranone 
• 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 
• 6909-21-3 (-)-cis-Caran-trans-(5)-ol 
• 5208-49-1 cis-4-carene 
• 21425-83-2 1.1.3-Trimethyl-3-brom-5-aethyl-cyclopentanon-(2) 
• 1740-97-2 2-methyl-4-isopropylphenol 
• 105497-91-4 (4R,6R)-4-isopropyl-6-methylcyclohex-2-en-1-one 
• 6617-28-3 phthalic acid mono-((1S,3R,4S)-caran-4-yl ester) 
• 5208-43-5 toluene-4-sulfonic acid-((1S,3R,4S)-caran-4-yl ester) 
• 4175-97-7 4-nitro-benzoic acid-((1S,3R,4S)-caran-4-yl ester) 
• 6617-28-3 phthalic acid mono-((1S,3R,4R)-caran-4-yl ester) 

Relevant academic research and scientific papers

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.

Facile entry to the tetracyclic 5-7-6-3 tigliane ring system

(equation presented) A tandem anionic 5-exo-dig cyclization/Claisen rearrangement sequence was used to effect a facile, "one-pot" conversion of an appropriately substituted 4-alkyn-1-ol to the tetracyclic carbon core structure of phorbol. The synthesis was conducted using readily available nonracemic starting materials to provide the target structure as a single enantiomer in high chemical yield.

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).

Molecular rearrangements of α-(trans)- and β-(cis)-3,4-epoxycaranes in acid media

Configuration of the oxirane ring in stereoisomeric 3,4-epoxycaranes affects the direction of their skeletal rearrangements in liquid (HSO3F-SO2FCl) and over solid (TiO2/SO42-) superacids; in the latter case, compounds postulated as intermediates in the liquid-phase process have been isolated.

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.

Synthesis of Some Conjugated Caradienes from 3-Carene by the Wittig Reaction and Their Reactivity in the Diels-Alder Reaction

The applicability of the Wittig reaction for the preparation of conjugated cis-caradienes was studied by the preparation of 4-methyl-3(10)-carene (27).The method was applied for the study of the synthesis of 3-vinyl-3-apocarene (6), 4-methylene-3(10)-carene (7), 4-methyl-2-methylene-3(10)-carene (8), 4-isopropenyl-3-carene (9) and 4-isopropenyl-3-caren-2a-ol (11) starting from 3-carene (20).The reactivity of conjugated cis-caradienes 6,7 and 9 in the Diels-Alder reaction has also been studied.

Transformations of 3-carene oxide at rhenium-containing catalysts

The transformations of 3-carene oxide at rhenium-containing catalysts were studied.The introduction of rhenium into the catalytic system significantly increases the reaction rate and leads to the formation of compounds not previously encountered in the products from the isomerization of 3-carene oxide, i.e., 3-carene, 3(10),4-caradiene, 3,3,6-trimethylcycloheptanone, and 3-caren-10-ol.

LIGHT-MEDIATED TRANSFORMATIONS OF OLEFINS INTO ALCOHOLS: REACTIONS OF HYDROXYL RADICALS WITH CYCLOALKENES

Reactions of hydroxyl radicals, generated by photodecomposition of hydrogen peroxide in acetonitrile, with a wide variety of cycloalkenes have been examined.The results show that the major reaction is the addition of hydroxyl radicals to the less substituted end of the double bond, furnishing the secondary alcohols.The reactivity pattern and the observed regio- and stereoselectivity clearly reveal that the steric parameters associated with the substrates play a dominant role in directing the addition reactions.More importantly, this study led to the development of a new methodology for the facile conversions of olefins essentially into secondary alcohols, and includes a few examples which demonstrate the potential of the method.

Studies on the Terpenoids and Related Alicyclic Compounds. XXXII. A Synthesis of Chiral Dimethylcyclopropane Derivatives, Versatile Chiral Synthons for Casbane, Lathyrane, and Ingenane-Type Diterpenoids, from (+)-3-Carene

A synthesis of chiral dimethylcyclopropane derivatives, useful for the synthesis of casbane, lathyrane, and ingenane-type diterpenoids, from easily available (+)-3-carene is described.The silyl enol ether (8) was derived from (-)-cis-4-caranone (7b), which was obtained from (+)-3-carene (6).Ozonolysis of 8 gave 9a and 10.The right half segment (11b) for a synthesis of crotonitenone (3) was formed from 9a in three steps.The epoxide (12) was isomerized to a mixture of the allylic alcohols (13a) and (14a), which was transformed to the ketone (20) in five steps.Methylation of 20 followed by phosphorylation and reduction gave (+)-cis-4-caranone (23) in about 40 percent overall yield from 12.The methylester (+)-(32b) and its enantiomer (-)-(34b) were synthesized from (+)-6.Ozonolysis of a mixture of the silyl enol ether (30) and (31) followed by methylation with diazomethane gave 32a, which was hydrolyzed to give the desired (+)-32b.The enantiomer (-)-34b was derived from 32a in five steps.