639086-18-3

Basic information

• Product Name: 2,4-Decadienamide, N-(2-methylpropyl)-, (2E,4Z)-
• CAS NO: 639086-18-3
• Molecular Formula: C14H25NO
• Molecular Weight: 223.359
• Mol File: 639086-18-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2,4-Decadienamide, N-(2-methylpropyl)-, (2E,4Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Decadienamide, N-(2-methylpropyl)-, (2E,4Z)-(639086-18-3)
• EPA Substance Registry System: 2,4-Decadienamide, N-(2-methylpropyl)-, (2E,4Z)-(639086-18-3)

Safety Data

• Hazardous Substances Data: 639086-18-3(Hazardous Substances Data)

Upstream product

• 4493-42-9 methyl (2E,4Z)-deca-2,4-dienoate 
• 118793-68-3 methyl (E)-dec-2-en-4-ynoate 
• 78651-48-6 (E)-dec-2-en-4-ynoic acid 
• 71256-94-5 (2E)-N-(2-methylpropyl)but-2-enamide 
• 3025-30-7 ethyl (2E,4Z)-2,4-decadienoate 
• 78-81-9 isobutylamine 
• 66-25-1 hexanal 
• 99083-26-8 (E)-(4-(isobutylamino)-4-oxobut-2-enyl)triphenylphosphonium bromide 
• 544-48-9 (2E,4Z)-decadienoic acid 

Downstream Products

• 18836-52-7 (2E,4E)-N-isobutyldecadienamide 

Relevant articles and documents

Stereoselective enzymatic synthesis of cis-pellitorine, a taste active alkamide naturally occurring in tarragon

The alkamide cis-pellitorine [(2E,4Z)-N-isobutyldeca-2,4-dienamide] that occurs naturally in tarragon was prepared in yields up to 80% by lipase-catalyzed conversion of ethyl 2E,4Z-decadienoate, the so-called pear ester, and isobutylamine both with and without the use of cosolvents. Of 13 different commercial enzyme preparations tested (lipases, proteases, esterases), only the lipase type B from Candida antarctica has a suitable activity. The reaction of the different geometric isomers of ethyl 2,4-decadienoate to the appropriate pellitorines shows a remarkable selectivity: the 2E,4Z ester is converted between 1.4 and 3.9 times faster than the 2E,4E isomer, and the relative yield of cis-pellitorine compared with trans-pellitorine is 5.7 to 16.3 times higher. In contrast to the better known frans-pellitorine, which at 10 ppm is only slightly tingling and numbing, cis-pellitorine shows very interesting pungent and warming sensations after tasting trials already in low concentrations of 10 ppm. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

PRODUCTION OF CIS-PELLITORIN AND USE AS A FLAVOURING

The invention relates to a method for producing 2E,4Z-decadienoic acid-N-isobutylamide (cis-pellitorin) and the use thereof as a pungent agent and a flavouring that generates heat, preferably in foodstuffs, oral hygiene or gourmet preparations.