58917-26-3

Basic information

• Product Name: (S)-(+)-6-METHYL-5-HEPTEN-2-OL
• Synonyms: (S)-(+)-6-METHYL-5-HEPTEN-2-OL;(S)-6-METHYL-5-HEPTEN-2-OL;(S)-6-Methyl-5-heptene-2-ol;(2S)-6-Methyl-5-heptene-2-ol;(S)-2-Methyl-2-heptene-6-ol;[2S,(+)]-6-Methyl-5-heptene-2-ol;(S)-sulcatol;(S)-6-methylhept-5-en-2-ol
• CAS NO: 58917-26-3
• Molecular Formula: C₈H₁₆O
• Molecular Weight: 128.21
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds
• Mol File: 58917-26-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 78-80°C 15mm
• Flash Point: 67°C
• Appearance: /
• Density: 0,844 g/cm3
• Refractive Index: 1.4480
• BRN: 1720071
• CAS DataBase Reference: (S)-(+)-6-METHYL-5-HEPTEN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-6-METHYL-5-HEPTEN-2-OL(58917-26-3)
• EPA Substance Registry System: (S)-(+)-6-METHYL-5-HEPTEN-2-OL(58917-26-3)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 58917-26-3(Hazardous Substances Data)

Usage

General Description

(S)-(+)-6-Methyl-5-hepten-2-ol is a chemical compound with the molecular formula C8H16O. It is a colorless liquid with a sweet, floral, and citrus-like odor. (S)-(+)-6-METHYL-5-HEPTEN-2-OL is commonly used in the fragrance and flavor industry due to its pleasant scent. It is also used as a flavoring agent in various food products. Additionally, (S)-(+)-6-Methyl-5-hepten-2-ol has applications in the production of perfumes, soaps, and cosmetics. It can also be used as a precursor in the synthesis of other organic compounds.

Upstream product

• 4630-06-2 6-methylhept-5-en-2-ol 
• 32807-28-6 Methyl 4-chloroacetoacetate 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 

Downstream Products

• 87247-19-6 (S)-6-Methylheptan-2-ol 
• 7492-31-1 (R)-isometheptene mucate 
• 1620401-56-0 (R)-6-methylamino-2-methylheptene 
• 155326-45-7 (-)-(5S,8R,13S,16R)-pyrenophorol 
• 1373756-63-8 (3S,6S)-6-tert-butyldiphenylsilyloxyhept-1-en-3-ol 
• 1039357-66-8 (3R,6S)-6-para-methoxybenzyloxyhept-1-en-3-ol 

Relevant articles and documents

Enantioselective enzymatic resolution of racemic alcohols by lipases in green organic solvents

The effects of two eco-friendly solvents, 2-methyltetrahydrofuran (MeTHF) and cyclopentyl methyl ether (CPME), on the enzyme activity and enantioselectivity of Novozym 435, Candida rugosa lipase (CRL), Porcine pancreas lipase (PPL), Lipase AK, Lipase PS, and Lipozyme, a series of commercial lipases, in the enantioselective transesterfications of racemic menthol, racemic sulcatol and racemic α-cyclogeraniol were studied. Vinyl acetate was chosen as the acyl donor and the reactions were carried out at water activity 0.06. The activity of lipases in CPME was similar to that observed in other largely employed organic solvents [toluene and tert-butyl methyl ether (MTBE)], and was slightly lower in MeTHF. However, for most of the lipases tested, the enantioselectivity was higher in the eco-friendly solvents. Lipase AK exhibited a high enantioselectivity (E?=?232) for the resolution of racemic menthol but the reaction rate was low. Lipase formulation (the enzyme was frozen and lyophilized in potassium phosphate buffer without and with 5% (w/v) of sucrose, D-mannitol, or methoxy poly(ethylene glycol)) was tested with this lipase in order to improve its activity, which increased up to 4.5 times, compared to the untreated enzyme. CALB was found to be a useful biocatalyst for the resolution of racemic sulcatol, where high activity and enantioselectivity were obtained (E?≥?1000). For the resolution of the racemic primary alcohol α-cyclogeraniol, most of the lipases tested were active but not enantioselective, except lipase PS which displayed a moderate enantioselectivity (E?=?19). The effect of the presence of a low percentage of two ionic liquids (ILs) 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([BMIM][TFSI]) (5% (v/v)) and 1-Butyl-3-methylimidazoliumtetrafluoroborate ([BMIM][BF4]) (1% (v/v)) in the medium was also investigated. Only in the case of CRL the ILs slightly increased the enantioselectivity from E?=?91 to E?=?103 and E?=?120 for [BMIM][TFSI] and [BMIM][BF4], respectively. However, in all cases ILs caused a decrease of enzyme activity.

Orchestration of concurrent oxidation and reduction cycles for stereoinversion and deracemisation of sec-alcohols

Black and white are opposites as are oxidation and reduction. Performing an oxidation, for example, of a sec-alcohol and a reduction of the corresponding ketone in the same vessel without separation of the reagents seems to be an impossible task. Here we show that oxidative cofactor recycling of NADP + and reductive regeneration of NADH can be performed simultaneously in the same compartment without significant interference. Regeneration cycles can be run in opposing directions beside each other enabling one-pot transformation of racemic alcohols to one enantiomer via concurrent enantioselective oxidation and asymmetric reduction employing defined alcohol dehydrogenases with opposite stereo- and cofactor-preference. Thus, by careful selection of appropriate enzymes, NADH recycling can be performed in the presence of NADP+ recycling to achieve overall, for example, deracemisation of sec-alcohols or stereoinversion representing a possible concept for a "green" equivalent to the chemical-intensive Mitsunobu inversion.

Kinetic resolution of racemic secondary alcohols via oxidation with Yarrowia lipolytica strains

Cyclic and alicyclic racemic secondary alcohols are kinetically resolved via oxidation with Yarrowia lipolytica strains. The comparison of the oxidation reactions with the reductions of the corresponding ketones supports the hypothesis of the presence of