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(1R,GR,SS)-6-Hydroxycaryophyllene (S)-6-hydroxystearate, a sesquiterpene alcohol esterified by the unusual fatty acid (S)(+)-6-hydroxystearic acid, has been isolated from the fruiting bodies of the Basidiomycete Lactarius subumbonatus. Both NMR data and AM1 calculations indicate that the caryophyllene macrocyclic ring adopts a beta beta conformation. The absolute configuration of the sesquiterpene moiety has been established by theoretical Circular Dichroism calculations (De Voe coupled oscillators theory) and that of the Salty acid by NMR studies of the (R)-2-methoxy-2-naphthylacetic acid (2-NMA) ester.

Fungal metabolites. 44 - Isolation of a new caryophyllane ester from Lactarius subumbonatus: Conformational analysis and absolute configuration

TOMA, LUCIO;VIDARI, GIOVANNI
1999-01-01

Abstract

(1R,GR,SS)-6-Hydroxycaryophyllene (S)-6-hydroxystearate, a sesquiterpene alcohol esterified by the unusual fatty acid (S)(+)-6-hydroxystearic acid, has been isolated from the fruiting bodies of the Basidiomycete Lactarius subumbonatus. Both NMR data and AM1 calculations indicate that the caryophyllene macrocyclic ring adopts a beta beta conformation. The absolute configuration of the sesquiterpene moiety has been established by theoretical Circular Dichroism calculations (De Voe coupled oscillators theory) and that of the Salty acid by NMR studies of the (R)-2-methoxy-2-naphthylacetic acid (2-NMA) ester.
1999
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
sì
WOS:000084006600008
Sì, ma tipo non specificato
Inglese
Internazionale
STAMPA
2059
2065
6
3
info:eu-repo/semantics/article
262
M., Clericuzio; Toma, Lucio; Vidari, Giovanni
1 Contributo su Rivista::1.1 Articolo in rivista
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1.1 Articolo in rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/455839
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