191670-18-5

Basic information

• Product Name: volicitin
• Synonyms: volicitin
• CAS NO: 191670-18-5
• Molecular Formula: C23H38N2O5
• Molecular Weight: 422.55822
• Mol File: 191670-18-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: volicitin(CAS DataBase Reference)
• NIST Chemistry Reference: volicitin(191670-18-5)
• EPA Substance Registry System: volicitin(191670-18-5)

Safety Data

• Hazardous Substances Data: 191670-18-5(Hazardous Substances Data)

Usage

Uses

(17S)-Volicitin is an insect elicitor.

Upstream product

• 51721-39-2 3-decyn-1-ol 
• 1642-49-5 dec-9-ynoic acid 
• 62285-66-9 methyl dec-9-ynoate 
• 100251-27-2 methyl 11-bromoundec-9-ynoate 
• 91966-51-7 11-hydroxy-9-undecynoic acid 
• 530099-04-8 (S)-17-Hydroxy-octadeca-9,12,15-triynoic acid methyl ester 
• 307524-20-5 (S)-17-hydroxylinolenic acid methyl ester 
• 530099-03-7 11-iodo-undec-9-ynoic acid methyl ester 
• 530099-02-6 (S)-3,6-heptadiyne-2-ol 
• 106031-47-4 11-bromo-undec-9-ynoic acid 
• 17696-11-6 8-bromooctanoic acid 
• 473451-78-4 methyl 15-[(tetrahydro-2H-pyran-2-yl)oxy]-9,12-pentadecadiynoate 
• 473451-79-5 methyl (9Z,12Z)-15-[(tetrahydro-2H-pyran-2-yl)oxy]-9,12-pentadecadienoate 
• 473451-81-9 methyl (9Z,12Z)-15-bromo-9,12-pentadecadienoate 

Relevant articles and documents

Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin

An efficient synthesis of N-(17S-hydroxylinolenoyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated.

Synthesis of volicitin: A novel three-component Wittig approach to chiral 17-hydroxylinolenic acid

A short stereoselective synthesis of both enantiomers of N-(17-hydroxylinolenoyl)-L-glutamine (volicitin) 12, an elicitor of plant volatile biosynthesis from beet armyworm salivary secretion, is described; the protected 17-hydroxylinolenic acid 4 moiety o