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| Names | |
|---|---|
| Preferred IUPAC name (1R,4S,4aS,6R,8aS)-4,8a,9,9-Tetramethyldecahydro-1,6-methanonaphthalen-1-ol | |
| Other names Patchouli camphor; (−)-Patchoulol; (1R,3R,6S,7S,8S)-Patchoulol; Patchouli alcohol | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.025.279 |
| EC Number |
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| KEGG | |
| UNII | |
| |
| |
| Properties | |
| C15H26O | |
| Molar mass | 222.36 |
| Appearance | white solid |
| Density | 1.0284 g/mL |
| Melting point | 56 °C (133 °F; 329 K) (racemic) |
| Boiling point | 287–288 °C (549–550 °F; 560–561 K) |
| practically insoluble | |
| Solubility inethanol | soluble |
| Solubility indiethyl ether | soluble |
Refractive index (nD) | 1.5029 |
| Hazards | |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Patchoulol orpatchouli alcohol (C15H26O) is asesquiterpene alcohol found inpatchouli.[1] Patchouli oil is an important material in perfumery[2]. The (−)-optical isomer is one of theorganic compounds responsible for the typical patchouli scent. Patchoulol is obtained by fermentation of leaves ofPogostemon cablin.[3]
Patchoulol is also used in the synthesis of the chemotherapy drugTaxol.[citation needed]
Gal first isolated patchouli alcohol in 1869, and Montgolfier later formulated its chemical composition (correctly) as C15H26O.[4] Early structural investigation soon established the presence of a saturated tricyclic tertiary alcohol.[5] After several years of careful degradation study,Büchi and co-workers proposed that patchouli alcohol had the structure1. A subsequent synthesis of material which corresponded to an authentic sample of natural patchouli alcohol appeared to verify Büchi's proposal.[6]
![Actual sequence for the synthesis of patchouli alcohol. Contains embedded bicyclo[2.2.2]octane motif.](/mt/?noimg=&dark=on&url=http%3a%2f%2fwww.wikipedia.org%2fwiki%2fFile%3aActual_sequence_patchouli_alcohol.png)
However,Dunitz and co-workers serendipitously discovered that Büchi's structure is in fact incorrect. Dunitzet al. had undertakenX-ray analysis of the patchouli alcohol diester withchromic acid, intending to determine the Cr-O-C angles. In the course of their analysis they could not reconcile the X-ray evidence with the "known" structure1.[7] In a joint paper with Büchi, they collectively proposed that patchouli alcohol in fact had the novel structure2. The discrepancy had resulted from an unanticipated skeletal rearrangement when patchoulene was treated withperoxy acid in Büchi's confirmatory synthesis. The rearranged molecule coincidentally exhibited the correct natural product architecture.[8]
