22556-08-7

Basic information

• Product Name: [1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol
• Synonyms: [1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol;EINECS 245-075-2;(1R)-1-Methyl-4β,5β-isopropylidenecyclohexane-1β,2α-diol;(1S,3R,6R)-3,7,7-Trimethylbicyclo[4.1.0]heptane-3β,4α-diol
• CAS NO: 22556-08-7
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.24872
• EINECS: 245-075-2
• Mol File: 22556-08-7.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 272.8°Cat760mmHg
• Flash Point: 126.6°C
• Appearance: /
• Density: 1.091g/cm³
• CAS DataBase Reference: [1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: [1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol(22556-08-7)
• EPA Substance Registry System: [1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol(22556-08-7)

Safety Data

• Hazardous Substances Data: 22556-08-7(Hazardous Substances Data)

Usage

General Description

The chemical "[1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol" is a bicyclic organic compound with a molecular formula C10H18O2. It is a stereochemically complex molecule with four chiral centers, resulting in several diastereomers. [1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol is known for its biological activity and is often used in pharmaceutical research. It is also used as a starting material for the synthesis of various natural products and pharmaceuticals. The compound has potential applications in medicine, drug development, and the production of functional materials. Its unique structure and biological properties make it a valuable target for further research and development.

Upstream product

• 498-15-7 (+)-Δ³-carene 
• 10395-46-7 1S,3R,4S,6R-(+)-3β,4β-caranediol 
• 67-64-1 acetone 
• 79-21-0 peracetic acid 
• 93-59-4 Perbenzoic acid 
• 2311-91-3 monoperoxyphthalic acid 
• 13466-78-9 3-carene 
• 936-91-4 (1S,3R,4S,6R)-3,4-epoxycarane 
• 936-91-4 α-3,4-Epoxycarane 
• 64-17-5 ethanol 
• 936-91-4 3-carene epoxide 
• 67-63-0 isopropyl alcohol 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 

Downstream Products

• 10309-65-6 (-)-4α-acetoxy-3β-hydroxy-trans-carane 
• 13124-69-1 4,7,7-trimethylbicyclo[4.1.0]heptan-3-one 
• 809286-04-2 (R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester 
• 809286-03-1 (S)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester 
• 58930-63-5 (3¹R,3³S)-3²,3²-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid 
• 24348-06-9 (+)-3β-hydroxy-4-caranone 
• 4017-83-8 (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 
• 36482-69-6 (1R,4S,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-one 
• 10395-46-7 (+)-3α,4β-caranediol 
• 33116-78-8 (1S,3R)-(+)-3-hydroxy-4-isocaranyl tosylate 
• 863225-01-8 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2R)-2-fluoro-2-[3-(phenylcarbonyl)phenyl]propionate 
• 863225-02-9 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2S)-2-fluoro-2-[3-(phenylcarbonyl)phenyl]propionate 
• 863224-97-9 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2R)-2-fluoro-2-(3-fluoro-4-phenylphenyl)propionate 

Relevant articles and documents

Sustainable catalytic protocols for the solvent free epoxidation and: Anti -dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H2O2 as oxidant

A tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and α-pinene oxide on a multigram scale, with the catalyst being recycled three times to produce 3-carene oxide. Epoxidation of the less reactive disubstituted alkene bonds of terpene substrates could be achieved by carrying out catalytic epoxidation reactions at 50 °C. Methods have been developed that enable direct epoxidation of untreated crude sulfate turpentine to afford 3-carene oxide, α-pinene oxide and β-pinene oxide. Treatment of crude epoxide products (no work-up) with a heterogeneous acid catalyst (Amberlyst-15) results in clean epoxide hydrolysis to afford their corresponding terpene-anti-diols in good yields.

Syntheses of the optically active terpene hydroxyphenylselenides

The optically active hydroxyphenylselenides derived from the p-menthane, carane, and pinane systems have been obtained. Two methods of hydroxyphenylselenides synthesis have been compared. The first method is based on the reaction of alkenes with N-(phenylseleno)succinimide in the presence of water, and the second from epoxides as a result of the reaction with sodium benzeneselenolate. The influence of the substrate structures on the composition of the obtained products has been demonstrated.

INTRODUCTION OF OXYGENATED FUNCTIONAL GROUPS INTO 3-CARENE AND 2-PINENE BY CULTURED CELLS

The biotransformation of the monoterpene hydrocarbons 3-carene and 2-pinene by cell suspension cultures of Nicotiana tabacum and Catharanthus roseus was investigated.The cultures have the ability to regio- and enantioselectively introduce the oxygenated functional groups into the C=C double bond and the allylic positions of the substrates. - Key words: Nicotiana tabacum; Solanaceae; Catharanthus roseus; Apocyanaceae; cultured cells; biotransformation; epoxidation; hydroxylation; carene; pinene.