112375-57-2

Basic information

• Product Name: (5E)-7-methyloct-5-enoyl chloride
• CAS NO: 112375-57-2
• Molecular Formula: C₉H₁₅ClO
• Molecular Weight: 174.6678
• Mol File: 112375-57-2.mol

Chemical Properties

• Boiling Point: 210.5°C at 760 mmHg
• Flash Point: 85.3°C
• Density: 0.972g/cm³
• Vapor Pressure: 0.191mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: (5E)-7-methyloct-5-enoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (5E)-7-methyloct-5-enoyl chloride(112375-57-2)
• EPA Substance Registry System: (5E)-7-methyloct-5-enoyl chloride(112375-57-2)

Safety Data

• Hazardous Substances Data: 112375-57-2(Hazardous Substances Data)

Upstream product

• 81077-23-8 (Z)-7-Methyl-oct-5-enoic acid 
• 14273-92-8 methyl 5-hydroxypentanoate 
• 112375-41-4 (Z)-methyl 7-methyloct-5-enoate 
• 61229-06-9 (E)-7-Methyloct-5-enoic acid 
• 59721-82-3 (E)-1-hydroxy-6-methylhept-4-ene 
• 112375-53-8 (E)-methyl 7-methyloct-5-enoate 
• 6026-86-4 methyl 4-formylbutanoate 
• 143211-14-7 (Z)-1-hydroxy-7-methyloct-5-ene 
• 143211-17-0 (E)-1-hydroxy-7-methyloct-5-ene 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 179617-47-1 trans-6-methyl-hept-4-enoic acid ethyl ester 
• 142331-60-0 (E)-7-methyl-5-octenenitrile 
• 179617-41-5 Methanesulfonic acid (E)-6-methyl-hept-4-enyl ester 

Downstream Products

• 112375-60-7 (Z)-N-(4-hydroxy-3-methoxybenzyl)-7-methyloct-5-enamide 
• 28789-35-7 Nordihydrocapsaicin 

Relevant articles and documents

A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement

Capsaicin, a main pungent principle of hot pepper, and its 15 analogs have been efficiently synthesized. The key step of this synthetic scheme is the orthoester Claisen rearrangement, which transformed allylic alcohols 2A-C to (E)-alkenoates 3A-C (E/Z > 100) in a highly stereoselective manner. The subsequent carbon chain elongations on 3 based on the cyanation or the malonic acid ester synthesis afforded (E)-alkenoic acids 8, which were converted to the corresponding acid chloride and then coupled with vanillylamine to give capsaicinoids. HPLC and CE (capillary electrophoresis) analyses of these capsaicinoids were also carried out.

An Alternate Synthesis of the Capsaicinoids

Five capsaicinoids, the pungent ingredients of hot peppers, have been efficiently synthesized by a method involving the Wittig reaction between isobutyl triphenylphosphorane and the appropriate lactols (3), followed by the nitrous acid-induced isomerization of the resultant (Z)-olefins (4) to (E)-olefins (5).

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.