24348-06-9

Usage

Uses

Used in Fragrance Industry:
[1R-(1α,4β,6α)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one is used as a fragrance ingredient for its pleasant, woody odor. It is commonly utilized in the production of perfumes, colognes, and other scented products, contributing to their overall aroma.
Used in Flavor Industry:
In the flavor industry, [1R-(1α,4β,6α)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one is used as a flavoring agent. It is added to various food and beverage products to enhance their aroma and taste, providing a unique and desirable sensory experience for consumers.
Used in Cosmetic Industry:
[1R-(1α,4β,6α)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one is also employed in the cosmetic industry, where it serves as a key ingredient in the formulation of scented products such as lotions, creams, and other personal care items. Its woody odor adds a pleasant and appealing fragrance to these products, making them more attractive to consumers.

Upstream product

• 22556-08-7 trans-3,4-caranediol 
• 936-91-4 3-carene epoxide 
• 498-15-7 (+)-Δ³-carene 
• 10395-46-7 1S,3R,4S,6R-(+)-3β,4β-caranediol 
• 93-59-4 Perbenzoic acid 
• 2311-91-3 monoperoxyphthalic acid 

Relevant academic research and scientific papers

Oxidation of terpenoid diols with chlorine dioxide: Preparation of ketols and α-chlorohydroxyketones of carane and pinane structures

Vicinal terpenoid diols of carane- and pinane-type structures have been oxidized with chlorine dioxide in pyridine to form the corresponding ketols in the preparative yield of 52-72%, the selectivity of α-hydroxyketones formation being 80-90%. It has been shown that the diols reactivity towards oxidation with ClO2 depends mainly on the stereochemistry of hydroxy groups. The catalysts, VO(acac)2, Mo(CO6), and MoCl 5 have practically no effect on the oxidation process. When the reaction has been performed in dimethylformamide, the hydroxyketone chlorination occurred at high conversion.

SYNTHESIS OF METHYL 1R-CIS-2,2-DIMETHYL-3-(2-OXOPROPYL)CYCLOPROPANECARBOXYLATE, AN INTERMEDIATE FOR SYNTHETIC PYRETHROIDS

Synthesis of keto ester (1) from (+)-3-carene is described.Ring cleavage is effected by the Beckmann Fragmentation.

Chromic Acid Oxidation of Some Oxiranes

Oxiranes derived from some alkenes, with olefinic bonds present in different stereoelectronic environments, have been treated with Cr(VI)-reagents.The major products obtained have been identified and their formation rationalized.In some cases, the method becomes synthetically useful for C-C bond cleavage.

STEREOCHEMISTRY OF THE CARANE SYSTEM. OXIDATION PRODUCTS OF ISOMERIC 3,4-CARANEDIOLS OBTAINED FROM (+)-3-CARENE

Oxidation of four isomeric 3,4-caranediols has been carried out and reaction products have been investigated.It has been found that cis-diols rather form cyclic ketals than are oxidized under conditions of the Jones reaction.The key intermediate for syntheses of chrysanthemic acid, (-)-2-acetonyl-3,3-dimethylcyclopropaneacetic acid was obtained exclusively by oxidation of (-)-3β,4α-caranediol.

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.

A New Synthesis of 1R-cis-2,2-Dimethyl-3-(2-oxopropyl)cyclopropanocarboxylic Acid from (+)-3-Carene

The title carboxylic acid (VII) has been obtained in good yield via the hydrogen peroxide epoxidation of furfurylidene derivative (IV) of the ketol intermediate (III) from (+)-3-carene (I) followed by oxidative cleavage with potassium permanganate.