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Δ-Cadinol
Chemical compound From Wikipedia, the free encyclopedia
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δ-Cadinol is an organic compound, a sesquiterpenoid alcohol produced by many plants as well as some animals and microorganisms. It is a white crystalline solid, soluble in isopropyl ether and ethanol. It is an epimer of α-cadinol.
δ-Cadinol exists in nature as either of two enantiomers distinguished by the prefixes (+)- and (−)-.[1][2] The (+)-isomer was identified by E. Shinozaki in 1922 from the leaves of Torreya nucifera and originally named torreyol.[1] The (−)-isomer was isolated in 1951 by Haagen-Smit and others from Pinus albicaulus and first called albicaulol.[1] Its structure was determined in 1970 by Lars Westfelt.[2] 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.[2][3] Lambertol is thought to be either (+)-δ-cadinol or (−)-δ-cadinol.[2] Cedrelanol was originally thought to be identical to (−)-δ-cadinol but was later confirmed to have the structure of τ-cadinol.[4]
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Occurrence
δ-Cadinol is produced by the fungus Xylobolus frustulatus as long white needles when grown in malt agar medium.[5] It also occurs in many conifers,[1] and in many other organisms including
- Achillea millefolium (6%)[6]
- Cedrela odorata[1]
- Clitocybe illudens (a mushroom)[3]
- Copaifera multijuga (1%; a major contributor to the aroma of copaiba oil)[7]
- Dictyopteris divaricata (a brown alga)[1]
- Plebejus argyrognomon (a butterfly; acts as a pheromone)[8]
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See also
- α-Cadinol
- τ-Cadinol
References
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