δ-Cadinol is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

, a

sesquiterpenoid Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modificati ...

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

produced by many plants as well as some animals and

microorganism A microorganism, or microbe,, ''mikros'', "small") and ''organism'' from the el, ὀργανισμός, ''organismós'', "organism"). It is usually written as a single word but is sometimes hyphenated (''micro-organism''), especially in olde ...

s. It is a white crystalline solid, soluble in

isopropyl ether Diisopropyl ether is secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industr ...

and

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

. It is an

epimer In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is ...

of α-cadinol. δ-Cadinol exists in nature as either of two

enantiomers In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical anti ...

distinguished by the prefixes (+)- and (−)-.Lars Westfelt (1970), "(−)-Torryeol ('δ-Cadinol')". ''Acta Chemica Scandinavica'' volume 24 issue 5 16181622 The (+)-isomer was identified by E. Shinozaki in 1922 from the leaves of ''

Torreya nucifera ''Torreya nucifera'' is a slow-growing, coniferous tree native to southern Japan and to South Korea's Jeju Island. It is also called Japanese torreya or Japanese nutmeg-yew. Description It grows to 15–25 m tall with a trunk up to 1.5 m diam ...

'' and originally named torreyol. The (−)-isomer was isolated in 1951 by Haagen-Smit and others from '' Pinus albicaulus'' and first called albicaulol. Its structure was determined in 1970 by Lars Westfelt. Other names were given to δ-cadinol based on its various biological sources before the structures were confirmed, including sesquigoyol for (+)-δ-cadinol and pilgerol for (−)-δ-cadinol. Lambertol is thought to be either (+)-δ-cadinol or (−)-δ-cadinol. Cedrelanol was originally thought to be identical to (−)-δ-cadinol but was later confirmed to have the structure of τ-cadinol.

Occurrence

δ-Cadinol is produced by the fungus '' Xylobolus frustulatus'' as long white needles when grown in

malt Malt is germinated cereal grain that has been dried in a process known as " malting". The grain is made to germinate by soaking in water and is then halted from germinating further by drying with hot air. Malted grain is used to make beer, wh ...

agar Agar ( or ), or agar-agar, is a jelly-like substance consisting of polysaccharides obtained from the cell walls of some species of red algae, primarily from ogonori (''Gracilaria'') and "tengusa" (''Gelidiaceae''). As found in nature, agar is ...

medium. It also occurs in many conifers, and in many other organisms including * ''

Achillea millefolium ''Achillea millefolium'', commonly known as yarrow () or common yarrow, is a flowering plant in the family Asteraceae. Other common names include old man's pepper, devil's nettle, sanguinary, milfoil, soldier's woundwort, and thousand seal. The ...

'' (6%) * ''

Cedrela odorata ''Cedrela odorata'' is a commercially important species of tree in the chinaberry family, Meliaceae, commonly known as Spanish cedar or Cuban cedar; it is also known as cedro in Spanish. Classification The genus ''Cedrela'' has undergone two m ...

'' * '' Clitocybe illudens'' (a

mushroom A mushroom or toadstool is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground, on soil, or on its food source. ''Toadstool'' generally denotes one poisonous to humans. The standard for the name "mushroom" is t ...

) * ''

Copaifera multijuga ''Copaifera'' is a genus of tropical plants in the legume family Fabaceae. The scientific name means "copal-bearer" (or more accurately, ''copaiba''-bearer), since economically important resins and essential oils can be acquired from them. They ...

'' (1%; a major contributor to the aroma of

copaiba Copaiba is a stimulant oleoresin obtained from the trunk of several pinnate-leaved South American leguminous trees (genus ''Copaifera''). The thick, transparent exudate varies in color from light gold to dark brown, depending on the ratio of resi ...

oil) * '' Dictyopteris divaricata'' (a

brown alga Brown algae (singular: alga), comprising the class (biology), class Phaeophyceae, are a large group of multicellular algae, including many seaweeds located in colder waters within the Northern Hemisphere. Brown algae are the major seaweeds of the ...

) * ''

Plebejus argyrognomon ''Plebejus argyrognomon'', common name Reverdin's blue is a butterfly of the family Lycaenidae. The species is named after Jacques-Louis Reverdin. Subspecies Subspecies include: * ''Plebeius argyrognomon argyrognomon'' Korb & Bolshakov, 2011 ...

'' (a

butterfly Butterflies are insects in the macrolepidopteran clade Rhopalocera from the Order (biology), order Lepidoptera, which also includes moths. Adult butterflies have large, often brightly coloured wings, and conspicuous, fluttering flight. The ...

; acts as a

pheromone A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavio ...

)

References

{{DEFAULTSORT:Cadinol, delta- Sesquiterpenes

Occurrence

See also

References