109-26-2

Basic information

• Product Name: 2,4-Decadienamide,N-(2-methylpropyl)-
• Synonyms: 2,4-Decadienamide,N-isobutyl- (7CI,8CI); N-Isobutyl-2,4-decadienamide
• CAS NO: 109-26-2
• Molecular Formula: C₁₄H₂₅NO
• Molecular Weight: 223.3544
• Mol File: 109-26-2.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 368.7°Cat760mmHg
• Flash Point: 224.6°C
• Density: 0.882g/cm³
• PKA: 15.49±0.46(Predicted)
• CAS DataBase Reference: 2,4-Decadienamide,N-(2-methylpropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Decadienamide,N-(2-methylpropyl)-(109-26-2)
• EPA Substance Registry System: 2,4-Decadienamide,N-(2-methylpropyl)-(109-26-2)

Safety Data

• Hazardous Substances Data: 109-26-2(Hazardous Substances Data)

Usage

General Description

2,4-Decadienamide, N-(2-methylpropyl)-, also known as 2-methyl-2-propylheptanamide, is a chemical compound that belongs to the class of amides. It is a colorless to light yellow liquid with a characteristic odor. This chemical is primarily used as a flavoring agent in the food industry, particularly in the production of beverages, baked goods, and confectionery products. It is also used as a fragrance ingredient in cosmetics and personal care products. Additionally, 2,4-Decadienamide, N-(2-methylpropyl)- has potential applications in the pharmaceutical and agricultural industries. However, it is important to handle and use this chemical with caution as it may cause skin and eye irritation, and it is harmful if swallowed. Therefore, proper safety precautions and handling procedures should be followed when working with this compound.

Upstream product

• 116724-23-3 deca-2c,4c-dienoic acid 
• 108965-86-2 methyl (2Z,4Z)-2,4-decadienoate 
• 169294-89-7 deca-2,4-diynoic acid 
• 68676-77-7 (2Z,4E)-deca-2,4-dienoic acid 
• 544-48-9 (2E,4Z)-decadienoic acid 
• 4493-42-9 methyl (2E,4Z)-deca-2,4-dienoate 
• 42997-45-5 deca-2t,4t-dienoyl chloride 
• 78-81-9 isobutylamine 
• 2548-87-0 (E)-2-Octenal 
• 119826-61-8 N-(Isobutyl)aminocarbonylmethyltriphenylarsonium bromide 
• 628-71-7 1-Heptyne 
• 110922-34-4 (E)-N-(2-methylpropyl)-3-iodoacrylamide 
• 71256-94-5 (2E)-N-(2-methylpropyl)but-2-enamide 
• 7328-33-8 methyl (2E,4E)-decadienoate 

Downstream Products

• 24738-52-1 deca-2E,4E-dienoic acid 4-hydroxy-2-phenylethylamide 

Relevant articles and documents

Ene Reaction of Pummerer-Type Reaction Intermediate and Synthesis of Pellitorine

Pummerer-type reaction intermediate 2 of α-(methylthio)acetic acid (1) has been found to react with 1-alkenes to afford ene adducts 3. Pellitorine S was synthesized from the adduct 3d.

Ene reaction with pummerer-type reaction intermediate of α-(methylthio)isobutyl acetamide: A new synthesis of pellitorine

Pummerer-type reaction intermediate 2 of α-(methylthio)isobutyl acetamide (1) has been found to react with 1-alkenes to afford ene adducts 3. Pellitorine 4 was synthesized from the adduct 3d.

A CONVENIENT STEREOSELECTIVE SYNTHESIS OF CONJUGATED DIENOIC ESTERS AND AMIDE

(2E,4E)-Dienoic esters and amides could be synthesized via the stereoselective isomerization of the corresponding 2-ynoic esters and amides, respectively, under the catalysis of ruthenium or iridium complexes.

Stereoselective synthesis of natural (2E,4E)-dienamides and their synthetic analogs

A procedure has been developed for stereoselective synthesis of a number of naturally occurring (2E,4E)-dienamides and their analogs via palladium-catalyzed reaction of (1E)-1-iodoalk-1-enes with acrylamides. Pleiades Publishing, Ltd., 2012.

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.

A synthetic approach to natural dienamides of insecticidal interest

An efficient synthesis of dienamides of insecticidal interest has been stereoselectively achieved featuring a Stille cross-coupling reaction as the key step.

USE OF TRANS-PELLITORIN IN THE FORM OF AN AROMATIC SUBSTANCE

The invention relates to the use of N-isobutylamide 2E, 4E-decadien acid (trans-pellitorin) in the form of an aromatic substance, in particular a saliva stimulating aromatic substance preferably for food, buccal hygiene or gustatory preparations. The preparations, semifinished products, compounds of odorant, aromatic and gustatory substances which contain trans-pellitorin and a method for the production of said trans-pellitorin are also disclosed.