Applications Of Argentation Solid Phase Extraction To The Capsaicinoids: Purification Of Commercial Standards And Isolation Of Homodihydrocapsaicin (8-methyl) From 'bhut Jolokia'

Title:
Applications Of Argentation Solid Phase Extraction To The Capsaicinoids: Purification Of Commercial Standards And Isolation Of Homodihydrocapsaicin (8-methyl) From 'bhut Jolokia'
Authors:
Thompson, Robert Q.; Loa, Kathleen
Abstract:
Argentation solid phase extraction was employed to purify commercial standards of capsaicin (6-ene-8-methyl) and dihydrocapsaicin (8-methyl). The purity was improved from 96.7% to 99.6% and from 89% to 96%, respectively, with 75% and 60% yield, respectively. Reversed phase solid phase extraction, argentation solid phase extraction, and preparative liquid chromatography with a C30 phase were used to isolate capsaicinoids from the fruits of 'Bhut Jolokia' peppers. The compounds capsaicin (6-ene-8-methyl) and dihydrocapsaicin (8-methyl) comprised 74% and 21% of the total mass of capsaicinoids. respectively. The remaining 5% of the capsaicinoids mass included the compounds: nordihydrocapsaicin (7-methyl), N-vanillylnonanamide, two homocapsaicin isomers, N-vanillyldecanamide, and two homodihydrocapsaicin isomers. All but one of these compounds were identified by comparison to known standards. The presence of homodihydrocapsaicin (8-methyl) was confirmed by its absorbance at 280 nm, electrospray ions at m/z 322 and m/z 137, elution just prior to homodihydrocapsaicin (9-methyl), and a carbon-13 NMR spectrum that matched predicted chemical shifts.
Citation:
Thompson, Robert Q., and Kathleen Loa. 2011. "Applications Of Argentation Solid Phase Extraction To The Capsaicinoids: Purification Of Commercial Standards And Isolation Of Homodihydrocapsaicin (8-methyl) From 'bhut Jolokia'." Food Chemistry 126(3): 1424-1430.
Publisher:
Elsevier
DATE ISSUED:
2011-06
Department:
Chemistry
Type:
article
PUBLISHED VERSION:
10.1016/j.foodchem.2010.11.128
PERMANENT LINK:
http://hdl.handle.net/11282/310138

Full metadata record

DC FieldValue Language
dc.contributor.authorThompson, Robert Q.en_US
dc.contributor.authorLoa, Kathleenen_US
dc.date.accessioned2013-12-23T16:26:20Z-
dc.date.available2013-12-23T16:26:20Z-
dc.date.issued2011-06en
dc.identifier.citationThompson, Robert Q., and Kathleen Loa. 2011. "Applications Of Argentation Solid Phase Extraction To The Capsaicinoids: Purification Of Commercial Standards And Isolation Of Homodihydrocapsaicin (8-methyl) From 'bhut Jolokia'." Food Chemistry 126(3): 1424-1430.en_US
dc.identifier.issn0308-8146en_US
dc.identifier.urihttp://hdl.handle.net/11282/310138-
dc.description.abstractArgentation solid phase extraction was employed to purify commercial standards of capsaicin (6-ene-8-methyl) and dihydrocapsaicin (8-methyl). The purity was improved from 96.7% to 99.6% and from 89% to 96%, respectively, with 75% and 60% yield, respectively. Reversed phase solid phase extraction, argentation solid phase extraction, and preparative liquid chromatography with a C30 phase were used to isolate capsaicinoids from the fruits of 'Bhut Jolokia' peppers. The compounds capsaicin (6-ene-8-methyl) and dihydrocapsaicin (8-methyl) comprised 74% and 21% of the total mass of capsaicinoids. respectively. The remaining 5% of the capsaicinoids mass included the compounds: nordihydrocapsaicin (7-methyl), N-vanillylnonanamide, two homocapsaicin isomers, N-vanillyldecanamide, and two homodihydrocapsaicin isomers. All but one of these compounds were identified by comparison to known standards. The presence of homodihydrocapsaicin (8-methyl) was confirmed by its absorbance at 280 nm, electrospray ions at m/z 322 and m/z 137, elution just prior to homodihydrocapsaicin (9-methyl), and a carbon-13 NMR spectrum that matched predicted chemical shifts.en_US
dc.publisherElsevieren_US
dc.identifier.doi10.1016/j.foodchem.2010.11.128-
dc.subject.departmentChemistryen_US
dc.titleApplications Of Argentation Solid Phase Extraction To The Capsaicinoids: Purification Of Commercial Standards And Isolation Of Homodihydrocapsaicin (8-methyl) From 'bhut Jolokia'en_US
dc.typearticleen_US
dc.identifier.journalFood Chemistryen_US
dc.identifier.volume126en_US
dc.identifier.issue3en_US
dc.identifier.startpage1424en_US
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