A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement

Kaga, Harumi; Goto, Kouhei; Takahashi, Tomiki; Hino, Masao; Tokuhashi, Takashi; Orito, Kazuhiko

doi:10.1016/0040-4020(96)00414-0

Cited by 31 publications

(21 citation statements)

References 22 publications

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“…The acyl moiety of capsiate is an 8-methylnon-6-enoic acid, and that of dihydrocapsiate is an 8-methylnonanoic acid. The acyl donors can be produced by chemical synthesis, 29,30) although the process is complicated and the yield is low. Furthermore, commercial products are too expensive for application to practical use.…”

Section: Ešects Of Water Content and Additivesmentioning

confidence: 99%

Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases

Kobata

Kawaguchi

Watanabe

2002

Bioscience, Biotechnology, and Biochemistry

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Section: Ešects Of Water Content and Additivesmentioning

confidence: 99%

Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases

Kobata

Kawaguchi

Watanabe

2002

Bioscience, Biotechnology, and Biochemistry

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“…71240-51-2, that will be described here with the abbreviated name (E)-6-ene-8-methyl homocapsaicin or (E)-6,8-HC. Only eight literature citations were found for this capsaicinoid, 12,15,37,38,42,[64][65][66] all of which were duplicates in the set of 70 references mentioned above.…”

Section: Literature Searchmentioning

confidence: 99%

“…179617-82-4, a single (formal) name, 6-decenamide, N-[(4-hydroxy-3methoxyphenyl)methyl]-9-methyl, (E)-, and, surprisingly, only one literature citation, a synthesis. 42 Each of the other two compounds has a unique Registry No. and one literature reference, both to a paper by Thompson.…”

Section: Literature Searchmentioning

confidence: 99%

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Homocapsaicin: nomenclature, indexing and identification

Thompson

2007

Flavour & Fragrance J

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The complete literature of homocapsaicin, one of the spicy principals of chilli pepper (Capsicum spp.), is reviewed and analysed. Name, structure, and topic searches in Chemical Abstracts and other relevant databases, conducted in September 2006, found 74 references to the homocapsaicin isomers. Nearly all resulted from searches on homocapsaicin or homocapsaicin I or 7-decenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-9-methyl, (7E)-, names treated, unfortunately, as synonyms by Chemical Abstracts. A mere nine citations were linked to the 6-ene homocapsaicin isomers. Of the 74 citations, 28 did not refer to a specific homocapsaicin isomer and another 27 provided no evidence for their particular structural assignments. Consequently, the name 'homocapsaicin isomer', meaning a homocapsaicin isomer with unspecified positions of the double bond and methyl group along the acyl chain, would be a more accurate indexing term for the majority (74%) of the literature. Only nine journal articles described analytical studies with convincing evidence for the existence of specific homocapsaicin isomers. These studies found (E)-6-ene-8-methyl homocapsaicin and (E)-6-ene-9-methyl homocapsaicin, but not the (E)-7-ene-9-methyl isomer, in chilli peppers. The need, relevant to all the capsaicinoids, for new nomenclature, better indexing, more accurate identification of isomers, and available chemical standards is presented, and suggestions for improvements are made.

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“…Different non-pungent analogues of capsaicin can be synthesized using aromatic ring containing different functional groups and acyl chain of varying lengths [38] The by-products were two highly pungent and some low pungent analogues having promising utilities. Commercial capsaicinoid production is achieved by heating chlorinated fatty acids and amines at temperatures between 140 ο C and 170 °C in the presence of low pressure [57][58][59]. Choi and Yoon, conveyed the use of bioisosterism to synthesize a capsaicin analogue, namely, 1-hydroxy-2-pyridone showing activity similar to it [39].…”

Section: Artificial Methods Of Capsaicin Productionmentioning

confidence: 99%

In vitro production of capsaicin through plant tissue culture

Swetnisha

2017

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Capsaicin, a secondary metabolite produced in capsicum, is in high demand in pharmaceutical industry because of its various medicinal properties. Currently, the supply of capsaicin depends upon its extraction from capsicum fruits. This limits the production of capsaicin as it depends upon agricultural produce. The current review has compiled information from various literature published on chemistry and importance of capsaicin along with its method of production. It also reviews the process of in vitro production of capsaicin through plant tissue culture, strategies of increasing capsaicin accumulation and its advantages over extraction from fruits and artificial synthesis.

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A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement

Cited by 31 publications

References 22 publications

Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases

Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases

Homocapsaicin: nomenclature, indexing and identification

In vitro production of capsaicin through plant tissue culture

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