English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Plus annual

Presents the access of premium content as premium feature

Premium Content

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools annual

Global: Zendy Free Plan

Global: Zendy Tools monthly

Global: Zendy Plus monthly

The first straightforward synthesis of 16-hydroxycapsaicin, 17-hydroxycapsaicin and 16,17-dehydrocapsaicin, the major aliphatic metabolites of capsaicin, is reported. The amidation of hept-6-enoic acid with vanillylamine hydrochloride, followed by olefin metathesis using 2-methylbut-3-en-2-ol as partner furnished 16-hydroxycapsaicin in 56.1% overall yield with excellent  E -selectivity. The  E -selective olefin metathesis of methyl hept-6-enoate with but-3-en-2-one led to α,β-unsaturated ketone compound, which was subject to Wittig reaction with Ph 3 P + MeBr - , providing the corresponding 1,3-diene derivative. After removing methyl group by hydrolysis and introducing hydroxyl group by hydroboration-oxidation, such diene could be further converted to 16,17-dehydrocapsaicin and 17-hydroxycapsaicin with overall yields of 35.6 and 7.8%, respectively.

A practical synthesis of three aliphatic metabolites of capsaicin: 16-Hydroxycapsaicin, 17-hydroxycapsaicin, and 16,17-dehydrocapsaicin