18836-52-7

Usage

Uses

Used in Pharmaceutical Industry:
Pellitorine is used as a therapeutic agent for the treatment of hyperlipidemia and diabetes. Its ACAT inhibitory activity helps in reducing cholesterol synthesis and absorption, while its α-Glucosidase inhibitory activity aids in lowering postprandial blood glucose levels.

Synthesis Reference(s)

Synthetic Communications, 18, p. 77, 1988 DOI: 10.1080/00397918808057822Tetrahedron Letters, 29, p. 3949, 1988 DOI: 10.1016/S0040-4039(00)80390-1

InChI:InChI=1/C14H25NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h8-11,13H,4-7,12H2,1-3H3,(H,15,16)/b9-8+,11-10+

Upstream product

• 33966-50-6 SEC-BUTYLAMINE 
• 159766-46-8 E,E-2,4-decadienoic acid 
• 129377-79-3 N-isobutyl-dec-2-ynamide 
• 693-25-4 n-pentylmagnesium bromide 
• 79695-54-8 (E)-2-Benzenesulfinyl-dec-4-enoic acid isobutyl-amide 
• 3025-30-7 ethyl (2E,4Z)-2,4-decadienoate 
• 81442-45-7 2-methylthio-4-decenoic isobutyl amide 
• 139615-76-2 [((E)-Nona-1,3-diene)-2-sulfonyl]-benzene 
• 20334-54-7 2-chloro-octanal 
• 110922-33-3 (E)-N-(2-methylpropyl)-3-bromoacrylamide 
• 54542-97-1 (E)-1-heptenyldiisobutylaluminium 
• 60595-37-1 (E)-1-iodohept-1-ene 
• 35143-37-4 N-(2-methylpropyl)prop-2-enamide 
• 179949-87-2 (E)-4-(Toluene-4-sulfonyl)-but-2-enoic acid isobutyl-amide 

Downstream Products

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

Relevant academic research and scientific papers

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.

Conjugated dienamides, methods of production thereof, compositions containing same and uses thereof

Described are mixtures of at least four of the alkadienamides defined according to the structure: wherein R represents C1 - C2 n-alkyl; R1 is 2-methyl-1-propyl and R2 is hydrogen, or R1 and R2 taken together is a moiety having the formula wherein n is 4 or 5, or compositions containing substantial concentrations of such mixtures, prepared according to novel processes: (a) extraction of a ground substantially dried fruit of one of the Piper species, Piper longum Linn orPiper peepuloides; (b) natural product-forming synthesis; or (c) synthetic product-forming synthesis. Also described are uses of the thus-formed products for augmenting, enhancing or imparting an aroma, taste, chemesthetic effect and/or antibacterial effect in or to a consumable material and/or in the oral cavity and/or on the mammalian epidermis.

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.

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.

Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg-Baecklund reaction

A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a-1n by the recently developed one-flask Ramberg-Baecklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of sulfide 6 gave the corresponding sulfone 2. Treatment of the sulfone 2 with the dibromodifluoromethane in the presence of alumina-supported potassium hydroxide in dichloromethane solution afforded unsaturated amide alkaloids 1a-1n. To the best of our knowledge, the synthesis of 1e and 1i was reported for the first time.

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.

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 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.

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.

Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology

The Sakai aryl aldehyde - cyclic ketone aldol - Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substituents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal-cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal-cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids. The Sakai aryl aldehyde - cyclic ketone aldol - Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substitutents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal-cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal-cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids.