δ-Cadinol is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

, 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 combinations. Biochemical modifications such ...

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

produced by many plants as well as some animals and

microorganism A microorganism, or microbe, is an organism of microscopic scale, microscopic size, which may exist in its unicellular organism, single-celled form or as a Colony (biology)#Microbial colonies, colony of cells. The possible existence of unseen ...

s. It is a white crystalline solid, soluble in

isopropyl ether Diisopropyl ether is a 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 indus ...

and

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

. 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 t ...

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

enantiomers In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

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 dia ...

'' 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 ''Xylobolus frustulatus'', commonly known as the ceramic fungus or ceramic parchment, is an inedible species of crust fungi, crust fungus in the Stereaceae family. The basidiocarp, fruit body forms small, hard, flat crust-like aggregations that r ...

'' as long white needles when grown in

malt Malt is any cereal grain that has been made to germinate by soaking in water and then stopped from germinating further by drying with hot air, a process known as "malting". Malted grain is used to make beer, whisky, malted milk, malt vinegar, ...

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" and " tengusa". As found in nature, agar is a mixture of two components, t ...

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. Growing to tall, it is characterized by small whitish flowers, a tall stem of fernlike leaves, and a pungent odor. The plan ...

'' (6%) * ''

Cedrela odorata ''Cedrela'' is a genus of several species in the mahogany family, Meliaceae. They are evergreen or dry-season deciduous trees with pinnate leaves, native to the tropical and subtropical New World, from southern Mexico south to northern Argentina ...

'' * '' Clitocybe illudens'' (a

mushroom A mushroom or toadstool is the fleshy, spore-bearing Sporocarp (fungi), fruiting body of a fungus, typically produced above ground on soil or another food source. ''Toadstool'' generally refers to a poisonous mushroom. The standard for the n ...

) * '' Copaifera multijuga'' (1%; a major contributor to the aroma of

copaiba Copaiba is an 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 resin to esse ...

oil) * '' Dictyopteris divaricata'' (a

brown alga Brown algae (: alga) are a large group of multicellular algae comprising the class Phaeophyceae. They include many seaweeds located in colder waters of the Northern Hemisphere. Brown algae are the major seaweeds of the temperate and polar reg ...

) * '' Plebejus argyrognomon'' (a

butterfly Butterflies are winged insects from the lepidopteran superfamily Papilionoidea, characterized by large, often brightly coloured wings that often fold together when at rest, and a conspicuous, fluttering flight. The oldest butterfly fossi ...

; 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