25394-57-4

Basic information

• Product Name: N-ISOBUTYL-2,6,8-DECATRIENAMIDE
• Synonyms: N-ISOBUTYL-2,6,8-DECATRIENAMIDE;SPILANTHOL;AFFININ;(2E,6Z,8E)-N-Isobutyl-2,6,8-decatrienamide;SPILANTHOL(P);2,6,8-DecatrienaMide,N-(2-Methylpropyl)-, (2E,6Z,8E)-
• CAS NO: 25394-57-4
• Molecular Formula: C₁₄H₂₃NO
• Molecular Weight: 221.33900
• Mol File: 25394-57-4.mol

Chemical Properties

• Melting Point: 23°
• Boiling Point: bp0.2 141°; bp0.3-0.5 160-165°
• Flash Point: 234°C
• Appearance: /
• Density: 0.896g/cm³
• Vapor Pressure: 4.02E-06mmHg at 25°C
• Refractive Index: nD25 1.5134
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.07±0.46(Predicted)
• Stability: Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: N-ISOBUTYL-2,6,8-DECATRIENAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ISOBUTYL-2,6,8-DECATRIENAMIDE(25394-57-4)
• EPA Substance Registry System: N-ISOBUTYL-2,6,8-DECATRIENAMIDE(25394-57-4)

Safety Data

• Hazardous Substances Data: 25394-57-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
N-ISOBUTYL-2,6,8-DECATRIENAMIDE is used as a therapeutic agent for treating dry mouth (xerostomia). It acts as a saliva stimulant (sialogogue), helping to alleviate the symptoms of xerostomia by promoting saliva production in individuals suffering from this condition.
Used in Flavor and Fragrance Industry:
N-ISOBUTYL-2,6,8-DECATRIENAMIDE is used as a flavoring agent for its unique taste and aroma. Its distinct properties make it a valuable addition to the flavor and fragrance industry, where it can be used to enhance the sensory experience of various products.
Used in Cosmetics and Personal Care:
N-ISOBUTYL-2,6,8-DECATRIENAMIDE is used as an active ingredient in cosmetics and personal care products due to its potential benefits for skin health. Its biological activities may contribute to improved skin hydration, reduced inflammation, and enhanced skin barrier function.
Used in Agrochemicals:
N-ISOBUTYL-2,6,8-DECATRIENAMIDE can be used as a bioactive compound in the development of agrochemicals, such as pesticides and herbicides. Its unique chemical structure and biological activities may provide novel modes of action for controlling pests and weeds in agriculture.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 5177, 1984 DOI: 10.1016/S0040-4039(01)81556-2

InChI:InChI=1/C14H23NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h4-7,10-11,13H,8-9,12H2,1-3H3,(H,15,16)/b5-4+,7-6-,11-10+

Upstream product

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• 91061-06-2 trans,trans-Deca-2,8-dien-6-insaeure 
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• 628317-42-0 methyl 3-oxo-6,8-decadienoate 
• 1260673-09-3 methyl 3-hydroxy-6,8-decadienoate 
• 1260673-10-6 N-isobutyl-3-hydroxy-6,8-decadienamide 

Relevant articles and documents

A new approach for the total synthesis of spilanthol and analogue with improved anesthetic activity

A 5-step synthesis of spilanthol (affinin) is reported, where the route features complete control of alkene geometry during the assembling of the double bonds, with the use of a Sonogashira cross-coupling reaction, a Z-selective alkyne semi-reduction and a HWE olefination reaction as the key steps. A simplified analogue was also prepared in 4 steps. Both compounds were found to permeate dermatomed pig ear skin through an in vitro Franz-type diffusion cell. The simplified analogue presented a superior anesthetic effect in vivo, using the tail flick model, when compared to spilanthol and to the commercial standard EMLA. These results suggest that both spilanthol and its analogue could be useful as a topical anesthetic in clinical practice.

METHOD FOR MANUFACTURING SPILANTHOL AND INTERMEDIATE MANUFACTURING PRODUCT THEREFOR

Provided is an amide ester that is useful as an intermediate manufacturing product for an aroma compound such as spilanthol or the like. Also provided is a spilanthol manufacturing method using said amide ester. High-purity spilanthol can be manufactured by reacting an amide ester represented by general formula (1) with a basic compound. (In the formula, R1 represents a phenyl group that may be substituted with a C1-6 alkyl group and either a C1-4 alkyl group, a C1-4 alkoxy group, or a halogen atom; R2 represents a C1-8 hydrocarbon group; and the wavy lines represent cis configurations, trans configurations, or a mixture of the two configurations.)

Stereoselective Synthesis of 1,4-Disubstituted 1,3-Diene from Aldehyde Using Organotitanium Reagent

Organotitanium reagent generated from 1-t-butylthio-3-trimethylsilyl-1-propene condenses with aldehydes to give 1-t-butylthio-(E,Z)-1,3-alkadienes in a single step via (E)-erythro-β-hydroxysilane in a highly regio- and stereoselective manner. 1,4-Dialkyl-1,3-diene is obtained from the diene sulfide by crosscoupling reaction with Grignard reagent in the presence of nickel catalyst.The utility of the method is illustrated by application to the synthesis of Spilanthol, a naturally occurring insecticide from Spilanthese olerancae in five steps.

FACILE R0UTES TO NATURAL ACYCLIC POLIENES. SYNTHESES OF SPILANTHOL AND TRAIL PHEROMONE FOR TERMITE

The synthetic procedures for spilanthol and trail-following pheromone for a southern subterranean termite were described.The syntheses heavily depend on the new diene synthesis using titanium reagent.