delta-cadinol

Also known as δ-cadinol, torreyol, albicaulol, pilgerol, sesquigoyol

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.

Chemical data

Formula: C15H26O
Molecular weight: 222.37 g/mol
IUPAC name: (1R,4S,4aR,8aS)-1,6-dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-ol
SMILES: CC1=C[C@H]2[C@@H](CC[C@@]([C@H]2CC1)(C)O)C(C)C
InChIKey: LHYHMMRYTDARSZ-ZQDZILKHSA-N
XLogP: 3.3
Polar surface area: 20.2 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

via PubChem

Wikidata facts

Mass: 222.198365

Show 3 more facts

isomeric SMILES: CC1=C[C@H]2[C@@H](CC[C@@]([C@H]2CC1)(C)O)C(C)C
chemical formula: C₁₅H₂₆O
canonical SMILES: CC1=CC2C(CCC(C2CC1)(C)O)C(C)C

Sources (1)

wikidata.org

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Encyclopedic overview

3 sections

Contents

Occurrence
See also
References

δ-Cadinol exists in nature as either of two enantiomers distinguished by the prefixes (+)- and (−)-. The (+)-isomer was identified by E. Shinozaki in 1922 from the leaves of Torreya nucifera 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.

Excerpted from Wikipedia’s “delta-cadinol” article, available under the CC BY-SA 4.0 licence.