60593-11-5

Basic information

• Product Name: (S)-(+)-5-(1-HYDROXY-1-METHYLETHYL)-2-METHYL-2-CYCLOHEXEN-1-ONE
• Synonyms: 5-(1-Hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one;Carvone hydrate;(S)-(+)-CARVONE HYDRATE;(S)-(+)-5-(1-HYDROXY-1-METHYLETHYL)-2-METHYL-2-CYCLOHEXEN-1-ONE;(S)-(+)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cy;[S,(+)]-5-(1-Hydroxy-1-methylethyl)-2-methyl-2-cyclohexene-1-one
• CAS NO: 60593-11-5
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 186.25
• Mol File: 60593-11-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 40-42 °C(lit.)
• Boiling Point: 157-158 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.043 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00097mmHg at 25°C
• Refractive Index: n20/D 1.507(lit.)
• PKA: 14.74±0.29(Predicted)
• CAS DataBase Reference: (S)-(+)-5-(1-HYDROXY-1-METHYLETHYL)-2-METHYL-2-CYCLOHEXEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-5-(1-HYDROXY-1-METHYLETHYL)-2-METHYL-2-CYCLOHEXEN-1-ONE(60593-11-5)
• EPA Substance Registry System: (S)-(+)-5-(1-HYDROXY-1-METHYLETHYL)-2-METHYL-2-CYCLOHEXEN-1-ONE(60593-11-5)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• RIDADR: UN 2810 6.1/PG 2
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 60593-11-5(Hazardous Substances Data)

Usage

General Description

(S)-(+)-5-(1-HYDROXY-1-METHYLETHYL)-2-METHYL-2-CYCLOHEXEN-1-ONE is a chemical compound that belongs to the group of cyclohexenones. It is a chiral molecule with a specific stereochemistry, denoted by the (S)-(+)- prefix. (S)-(+)-5-(1-HYDROXY-1-METHYLETHYL)-2-METHYL-2-CYCLOHEXEN-1-ONE contains a cyclohexene ring with a hydroxyl and a methyl group attached, as well as an additional methyl group on the carbon adjacent to the hydroxyl. This chemical is commonly used as a building block in organic synthesis and can also be found as a flavoring agent in some food products. Its specific stereochemistry makes it an important starting material for the production of various pharmaceuticals and bioactive compounds.

InChI:InChI=1/C10H16O2/c1-7-4-5-8(6-9(7)11)10(2,3)12/h4,8,12H,5-6H2,1-3H3/t8-/m0/s1

Upstream product

• 38235-58-4 trans-sobrerol 
• 56423-45-1 (4S,8RS)-8,9-epoxy-p-menth-6-en-2-one 
• 7785-70-8 (+)-α-pinene 
• 32226-54-3 trans-sobrerol 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 

Downstream Products

• 499-75-2 carvacrol 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 111323-96-7 C₁₇H₂₄N₂O₃S 
• 2437-97-0 (+/-)-4,7,7-trimethyl-6-oxabicyclo<3.2.1>oct-3-ene 
• 38235-58-4 trans-sobrerol 
• 454-77-3 1(S)-5(S)-(+)-cis-sobrerol 

Relevant articles and documents

Formation of trans-verbenol and verbenone from α-pinene catalysed by immobilised Picea abies cells

Both enantiomers and the raceinate of α-pinene were transformed by Picea abies cells immobilised on alginate. The main products were cis- and trans-verbenol, the later being further transformed to verbenone. The enantiomeric purity of each product more or less corresponded to that of the substrate. Transformation by free cells was faster than that by the immobilised cells. The ratio of products differed to some extent between the transformation by tree and immobilised cells.

Palladium-catalyzed aerobic oxidative kinetic resolution of alcohols with an achiral exogenous base

Substitution of exogenous (-)-sparteine for a more practical achiral base in the aerobic oxidative kinetic resolution of secondary alcohols is described. Carbonate bases are the most effective of those screened and allow for effective kinetic resolution of benzylic, allylic, and aliphatic substrates. The procedure was also successfully extended to the oxidative desymmetrization of meso diols.

Pheromone Synthesis, CIV.- Synthesis of the Enantiomers of α-Phellandren-8-ol (p-Mentha-1,5-dien-8-ol), a Monoterpene from Bark Beetles

Enantiomerically pure (R)-α-phellandren-8-ol (p-mentha-1,5-dien-8-ol, 1a) was synthesized from (R)-carvone (2).Similarly (S)-1a was synthesized from (S)-2.