31467-60-4

Basic information

• Product Name: CIS 8-METHYLNON-6-ENOIC ACID
• Synonyms: (CIS)-8-METHYLNON-6-ENOIC ACID;(6Z)-8-Methyl-;(6Z)-8-methyl-6-nonenoic acid;(6Z)-8-methylnon-6-enoic acid;ZK-B
• CAS NO: 31467-60-4
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• Product Categories: Aliphatics
• Mol File: 31467-60-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 107-109 °C(Press: 3.5 Torr)
• Appearance: /
• Density: 0.934±0.06 g/cm3(Predicted)
• PKA: 4.75±0.10(Predicted)
• CAS DataBase Reference: CIS 8-METHYLNON-6-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: CIS 8-METHYLNON-6-ENOIC ACID(31467-60-4)
• EPA Substance Registry System: CIS 8-METHYLNON-6-ENOIC ACID(31467-60-4)

Safety Data

• Hazardous Substances Data: 31467-60-4(Hazardous Substances Data)

Usage

Chemical Properties

CIS 8-METHYLNON-6-ENOIC ACID is Light Yellow Oil

Uses

CIS 8-METHYLNON-6-ENOIC ACID is used in the synthesis of Capsaicin analogues, useful for their anti-tumor activity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 3477, 1989 DOI: 10.1021/jo00275a040

Upstream product

• 112375-42-5 methyl (6Z)-8-methylnon-6-enoate 
• 4224-70-8 6-bromohexanoic acid 
• 50889-29-7 (5-carboxypentyl)triphenylphosphonium bromide 
• 78-84-2 isobutyraldehyde 
• 148999-69-3 (6-methoxy-6-oxohexyl)triphenylphosphonium bromide 
• 4547-43-7 methyl 6-hydroxycaproate 
• 6654-36-0 methyl 6-oxohexanoate 
• 502-44-3 hexahydro-2H-oxepin-2-one 

Downstream Products

• 59320-77-3 trans-8-methyl-6-nonenoic acid 
• 205687-01-0 capsiate 
• 1073340-78-9 4-t-butyldimethylsilyloxy-3-methoxybenzyl (E)-8-methylnon-6-enoate 
• 95636-02-5 (E)-8-Methylnon-6-enoic acid chloride 
• 404-86-4 capsaicin 
• 25775-90-0 cis-capsaicin 
• 19408-84-5 dihydrocapsaicin 

Relevant articles and documents

Aliphatic hydroxylation and epoxidation of capsaicin by cytochrome P450 CYP505X

Microbial cytochrome P450 enzymes (CYPs) are able to mimic the metabolism of human CYPs. One challenge is to identify the respective drug metabolites and to compare substrate specificities to those of the human enzymes. In this study, a class VIII self-sufficient CYP from Aspergillus fumigatus (CYP505X) and variants of this enzyme were heterologously expressed in E. coli. The substrate scope of the variants was determined using active pharmaceutical ingredients (APIs) and (hetero)cyclic compounds. Capsaicin – the active compound in chili peppers – was oxidized most efficiently (4.36 μM/min) in a whole cell mediated biotransformation. The products were isolated, purified and their structures elucidated by 1D and 2D NMR. The two major metabolites showed modifications on the lipophilic side chain. Specifically, capsaicin was hydroxylated at position 8 to give (E)-8-hydroxy-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide and epoxidized at the double bond to give N-(4-hydroxy-3-methoxybenzyl)-5-(3-isopropyloxiran-2-yl)-pentanamide.

PRODUCTION METHOD OF CAPSINOID BY DEHYDRATING CONDENSATION, STABILIZING METHOD OF CAPSINOID, AND CAPSINOID COMPOSITION

In the production methods of capsinoid by esterification using an enzyme, a method of conveniently obtaining capsinoid in a high yield in a short time without using a dehydrating agent is provided. In addition, a method of stable preservation of produced capsinoid by purifying the obtained capsinoid under stable conditions is provided. A fatty acid represented by the formula (1) and a hydroxymethylphenol represented by the formula (2) are condensed without solvent or in a low-polar solvent, using an enzyme as a catalyst to give an ester compound represented by the formula (3). In addition, a fatty acid represented by the formula (4) is added to the ester compound represented by the formula (3) for stabilization. wherein each symbol is as defined in the specification.

The Capsaicinoids: Their Separation, Synthesis, and Mutagenicity

Capsaicin (1b), the pungent ingredient in many varietes of Capsicums has recently been implicated as a possible carcinogen.When obtained from natural sources 1b is always accompanied by a number of related homologues.We have isolated seven of these homologues, characterized them, and synthesized them by a general and unique route developed in our laboratories.Also reported are mutagenicity data for 1b and an extract of red pepper as measured by the Ames assay and the V-79 mammalian cell assay.