δ-Cadinol
| Names | |
|---|---|
| IUPAC name
(1S,4S)-1,6-Dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-ol
| |
| Other names
Torreyol
1-epi-α-Cadinol 1β-Cadin-4-en-10-ol | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C 15H 26O | |
| Molar mass | 222.37 g/mol |
| Appearance | White crystalline needles |
| Melting point | 138 to 139 °C (280 to 282 °F; 411 to 412 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
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]
Occurrence
[edit | edit source]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]
See also
[edit | edit source]References
[edit | edit source]- ^ a b c d e f Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c d Lars Westfelt (1970), "(−)-Torryeol ('δ-Cadinol')". Acta Chemica Scandinavica volume 24 issue 5 16181622 Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).