36482-69-6

Basic information

• Product Name: [1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one
• Synonyms: [1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one;(-)-3α-Hydroxycaran-4-one;(1R,6β)-4β-Hydroxy-4α,7,7-trimethylbicyclo[4.1.0]heptane-3-one;[1S,6R,(-)]-3,7,7-Trimethyl-3α-hydroxybicyclo[4.1.0]heptane-4-one;Einecs 253-056-5
• CAS NO: 36482-69-6
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 253-056-5
• Mol File: 36482-69-6.mol

Chemical Properties

• Boiling Point: 253.1°Cat760mmHg
• Flash Point: 104.5°C
• Appearance: /
• Density: 1.081g/cm³
• CAS DataBase Reference: [1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: [1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one(36482-69-6)
• EPA Substance Registry System: [1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one(36482-69-6)

Safety Data

• Hazardous Substances Data: 36482-69-6(Hazardous Substances Data)

Usage

Uses

Used in Fragrance and Flavor Industry:
[1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one is used as a key ingredient in the fragrance and flavor industry for its pleasant odor. It contributes to the production of perfumes and food flavorings, enhancing the sensory experience of consumers.
Used in Pharmaceutical Production:
[1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one is also utilized in the production of pharmaceuticals, capitalizing on its potential benefits in the medical field. Its properties make it a valuable component in the development of new drugs and therapies.
Used as a Starting Material in Organic Synthesis:
[1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one serves as a starting material in organic synthesis, allowing for the creation of a variety of other chemical compounds with different applications.
Used in Antioxidant and Anti-Inflammatory Applications:
Due to its antioxidant and anti-inflammatory properties, [1R-(1alpha,4alpha,6alpha)]-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one has potential applications in the development of new pharmaceuticals targeting conditions that benefit from these properties, such as inflammation-related diseases and oxidative stress-related disorders.

InChI:InChI=1/C10H16O2/c1-9(2)6-4-8(11)10(3,12)5-7(6)9/h6-7,12H,4-5H2,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 498-15-7 (+)-Δ³-carene 
• 10395-46-7 (+)-3α,4β-caranediol 
• 57457-02-0 cis-3α,4α-caranediol 
• 67-64-1 acetone 
• 33116-78-8 (1S,3R)-(+)-3-hydroxy-4-isocaranyl tosylate 
• 10395-46-7 1S,3R,4S,6R-(+)-3β,4β-caranediol 
• 22556-08-7 trans-3,4-caranediol 
• 1266680-97-0 (5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 100-39-0 benzyl bromide 
• 513-38-2 Isobutyl iodide 
• 78-77-3 Isobutyl bromide 
• 542-69-8 1-iodo-butane 
• 109-65-9 1-bromo-butane 

Downstream Products

• 1266680-98-1 (3S,5aR,6aS,7aS)-3-benzyl-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 1266681-00-8 (3S,5aR,6aS,7aS)-3-(4-nitrobenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 1266681-01-9 (3S,5aR,6aS,7aS)-3-(4-bromobenzyl)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 1266681-16-6 (3S,5aR,6aS,7aS)-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(3-phenylpropyl)bicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 

Relevant articles and documents

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.

Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1s)-(+)-3-carene derived tricyclic iminolactone

A novel carene-based alanine-equivalent tricyclic iminolactone 16 has been synthesized via stereoselective dihydroxylation of the double bond, IBX oxidation of the secondary alcohol, esterification of the tertiary alcohol, deprotection of the resulting ester, and subsequent cyclization from commercially available (1S)-(+)-3-carene in 79% overall yield. The iminolactone 16 demonstrated high reactivity toward alkylation with a wide range of electrophiles at room temperature under phasetransfer catalysis conditions. The alkylated products were produced with excellent diastereoselectivities (>98% de) in good isolated yields (86-94%). High yields (83-91%) of optically pure (S)-R-methyl-R-substituted-R-amino acids were obtained by basic hydrolysis of the dialkylated iminolactones with the recovery of the chiral auxiliary 15 (78-87%).

MODIFIED OXIDATION OF (+)-3-CARENE BY POTASSIUM PERMANGANATE

The oxidation of (+)-3-carene under the conditions of phase-transfer catalysis has been studied.It has been shown that when the reaction is performed in acetic acid the keto acids (IIa) and (IIIa) and (-)-3α-hydroxycaran-4-one (IV) are formed.

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.