Off-line mass spectrometric monitoring of HPLC effluents — an improved identification and quantitation method for mixtures of similar compounds: Natural capsaicinoids

Heresch, F.; Jurenitsch, J.

doi:10.1007/bf02302940

Cited by 31 publications

(11 citation statements)

References 12 publications

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“…The principle capsaicinoids present are 6,7‐dihydrocapsaicin ( 1 ) and capsaicin ( 2 ), amides between a unit of vanillylamine and a C 10 branched‐chain carboxylic acid. These compounds, which are responsible for the hot pungent taste, typically represent about 90 % of the capsaicinoid content of the fruits and the oleoresins derived therefrom, with the remaining 10 % being a mixture of various homologues 8, 9…”

Section: Introductionmentioning

confidence: 99%

Natural Deuterium Distribution in Branched-Chain Medium-Length Fatty Acids is Nonstatistical: A Site-Specific Study by Quantitative 2H NMR Spectroscopy of the Fatty Acids of Capsaicinoids

et al. 2002

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Quantitative 2H NMR spectroscopy has been used to determine the natural abundance site-specific 2H isotopic content of 6,7-dihydrocapsaicin (1) and capsaicin (2). Prior to analysis, the fatty acyl moieties were released as methyl 8-methylnonanoate (3) and methyl E-8-methylnon-6-enoate (4), respectively. A marked and similar nonstatistical isotopic distribution of (2)H is observed for both fatty acids. Notably, it can be seen that: 1) the isobutyl portion of 3 is more impoverished in 2H than the methylenic portion; 2) the isobutyl portion of 4 is more impoverished than that of 3; 3) an alternating pattern occurs in the (2H/1H)i between the C3 to C7 positions; and 4) the ethylenic hydrogens at C6 and C7 of 4 are, respectively, impoverished and unchanged relative to these positions in 3. These observations are compatible with the proposed biosynthetic origins of the different parts of 1 and 2, and with the view that 1 is a proximal precursor of 2. Furthermore, it can be suggested that, firstly, the hydrogen atoms at C3 to C7 originate alternatively from the substrate and from the environment and, secondly, that the Delta6-E desaturation is introduced by a mechanism closely mimicking that of the Z desaturation of higher plants.

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Section: Introductionmentioning

confidence: 99%

Natural Deuterium Distribution in Branched-Chain Medium-Length Fatty Acids is Nonstatistical: A Site-Specific Study by Quantitative 2H NMR Spectroscopy of the Fatty Acids of Capsaicinoids

et al. 2002

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“…Only trans-isomers of capsaicinoids with a double bond in a side chain were found in extracts of Capsicum fruits and no cis-isomers (Rangoonwala, 1969;Rangoonwala and Seitz, 1970;Jurenitsch et al, 1979b;Suzuki et al, 1980). Recently, there have been many more naturally occurring capsaicinoids identified such as homodihydrocapsaicin II (vanillylamide of 8-methyldecanoic acid), homocapsaicin II (vanillylamide of 8-methyldec-trans-6-enoic acid), vanillylamides of octanoic, nonanoic and decanoic acids which had, heretofore, been considered to be synthetic analogues (Jurenitsch et al, 1979b;Heresch and Jurenitsch, 1979), bishomocapsaicin and tris-homocapsaicin (Jurenitsch et al, 1979b) and nordihydrocapsaicin II (Jurenitsch and Woginger, 1982). These vanillylamides constitute the minor portion of total capsaicinoids in capsicum extracts (Jurenitsch et al, 1979a;Jurenitsch and Leinmuller, 1980) and have been assumed not to have much effect on total pungency.…”

Section: Introductionmentioning

confidence: 99%

Sensory Properties of Naturally Occurring Capsaicinoids

Krajewska

Powers

1988

Journal of Food Science

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Sensory evaluation of isolated natural capsaicinoids showed that there was a significant linear relationship between pungency and concentration. Detection thresholds were evaluated using an ASTM method. Pungency thresholds were calculated using the established relationships between pungency and concentration of individual compounds. Total pungency of a mixture of capsaicinoids was highly correlated with the sum of pungencies of individual capsaicinoids. Determination of the total pungency of Cupsicum extracts can be accomplished by adding the pungencies of individual capsaicinoids upon multiplication of their pungency threshold values by their respective concentrations.

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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%

“…A total of 28 reports, 2,5,7,11,13,[16][17][18]20,21,[23][24][25][26][30][31][32][33][34]39,44,46,50,51,58,64,68,72 including 17 patents, seem to draw attention to any and all of the isomers of homocapsaicin, without specificity. The next largest category of references, in contrast, does equate homocapsaicin and a specific isomer, albeit without explanation or evidence.…”

Section: Literature Analysismentioning

confidence: 99%

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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Off-line mass spectrometric monitoring of HPLC effluents — an improved identification and quantitation method for mixtures of similar compounds: Natural capsaicinoids

Cited by 31 publications

References 12 publications

Natural Deuterium Distribution in Branched-Chain Medium-Length Fatty Acids is Nonstatistical: A Site-Specific Study by Quantitative 2H NMR Spectroscopy of the Fatty Acids of Capsaicinoids

Natural Deuterium Distribution in Branched-Chain Medium-Length Fatty Acids is Nonstatistical: A Site-Specific Study by Quantitative 2H NMR Spectroscopy of the Fatty Acids of Capsaicinoids

Sensory Properties of Naturally Occurring Capsaicinoids

Homocapsaicin: nomenclature, indexing and identification

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