492458-54-5

Basic information

• Product Name: 1,2-Cyclohexanediol, 4-(2R)-oxiranyl-, (1R,2R,4S)- (9CI)
• Synonyms: 1,2-Cyclohexanediol, 4-(2R)-oxiranyl-, (1R,2R,4S)- (9CI)
• CAS NO: 492458-54-5
• Molecular Formula: C8H14O3
• Molecular Weight: 158.19496
• Product Categories: ALCOHOL
• Mol File: 492458-54-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Cyclohexanediol, 4-(2R)-oxiranyl-, (1R,2R,4S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclohexanediol, 4-(2R)-oxiranyl-, (1R,2R,4S)- (9CI)(492458-54-5)
• EPA Substance Registry System: 1,2-Cyclohexanediol, 4-(2R)-oxiranyl-, (1R,2R,4S)- (9CI)(492458-54-5)

Safety Data

• Hazardous Substances Data: 492458-54-5(Hazardous Substances Data)

Usage

Explanation

The molecular formula represents the number of atoms of each element present in a molecule of the compound.

Explanation

The compound consists of a six-membered cyclohexane ring with two hydroxyl groups at the 1 and 2 positions and an epoxide group at the 4 position.

Explanation

The stereochemistry of the compound is defined by the arrangement of atoms in three-dimensional space, with the R and S descriptors indicating the configuration of the chiral centers.

Explanation

The compound is a liquid at room temperature, with no color and no distinct smell.

Explanation

The compound is used in various industries due to its versatile chemical properties, including the production of pharmaceuticals, fragrances, and other organic compounds. It also serves as a solvent and is used in the synthesis of polymers and resins.

Explanation

The compound's chemical properties, such as its reactivity with different reagents, make it a valuable and versatile compound in the chemical industry.

Explanation

As with any chemical compound, it is essential to be aware of potential hazards and follow appropriate safety precautions when handling, storing, or using 1,2-Cyclohexanediol, 4-(2R)-oxiranyl-, (1R,2R,4S)(9CI).

Structure

Cyclohexane ring with two hydroxyl (-OH) groups and an epoxide functional group

Stereochemistry

(1R,2R,4S)

Physical State

Colorless, odorless liquid

Industrial Applications

Pharmaceutical precursor, fragrances, organic compounds, solvent, polymers, and resins

Chemical Properties

Reactivity with various reagents, versatile in the chemical industry

Safety

Potential hazards and precautions should be considered

Relevant articles and documents

Stereochemical aspects in the 4-vinylcyclohexene biotransformation with rat liver microsomes and purified cytochrome P450s: Diepoxide formation and hydrolysis

The stereochemical course of the biotransformation of 1,2-monoepoxides of 4-vinylcyclohexene (2 and 3) by liver microsomes from control and induced rats and by purified P4502B1 and P4502E1 has been determined. The epoxidation of monoepoxides cis-4-vinylcyclohexene 1,2-epoxide (2) and trans-4-vinylcyclohexene 1,2-epoxide (3) gives the corresponding eight isomeric diepoxides cis-4-vinylcyclohexene diepoxide (9) and trans-4-vinylcyclohexene diepoxide (10). The stereoselectivity of this process is affected by P450 induction. Phenobarbital is able to enhance the yield of epoxidation to give preferentially diepoxide (1R,2S,4R,7R)-trans-10b. This enantiomer is also formed as nearly the sole product by P450-catalyzed epoxidation of (1R,2S,4R)-trans-3b, the monoepoxide that, as a consequence of the selective formation from 4-vinylcyclohexene and/or reduced elimination by epoxide hydrolase, tends to accumulate in rat. Also, the P4502B1 but not 2E1, in a reconstituted system, is able to perform the epoxidation of (1R,2S,4R)-trans-3b to produce selectively the same diepoxide. Diepoxides cis-9 and trans-10 are biotransformed by mEH catalyzed hydrolysis. Although the hydrolysis of diepoxides 9 is characterized by a lower substrate enantioselection, the reaction of diepoxides 10 occurs with a good substrate enantioselectivity favoring the hydrolysis of the epoxides (1R,2S,4R,7S)-trans-10b and (1S,2R,4S,7S)-trans-10a. Diepoxide (1R,2S,4R,7R)-trans-10b is therefore the isomer primarily formed by P450-catalyzed oxidation of monoepoxide trans-3, and it is also the compound showing the lower propensity to undergo mEH-catalyzed hydrolysis. On the basis of this result, the ovotoxicity of 4-vinylcyclohexene is expected to be due to the stereoisomer diepoxide (1R,2S,4R,7R)-trans-10b, whose biological reactivity, via cross-linking, may be strongly different to the other isomer diepoxides, being dependent by its specific conformation.