Patchoulol

Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli.[1] Patchouli oil is an important material in perfumery. The (−)-optical isomer is one of the organic compounds responsible for the typical patchouli scent. Patchoulol is also used in the synthesis of the chemotherapy drug Taxol.

Patchoulol
Names
IUPAC name
3,4,4αβ,5,6β,7,8,8α-Octahydro-4α,8αβ,9,9-tetramethyl-1,6-methanonaphthalen-1β(2H)-ol
Other names
Patchouli camphor;
(–)-patchoulol;
(1R,3R,6S,7S,8S)-patchoulol;
patchouli alcohol
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
ECHA InfoCard 100.025.279
EC Number
  • 227-807-2
KEGG
UNII
Properties
C15H26O
Molar mass 222.36
Appearance Hexagonal-trapezohedral crystals
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 in ethanol soluble
Solubility in diethyl ether soluble
1.5029
Hazards
Safety data sheet External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Structure determination

Patchouli alcohol was first isolated in 1869 by Gal and its chemical composition later correctly formulated as C15H26O by Montgolfier.[2] During early structural investigation the presence of a saturated tricyclic tertiary alcohol was established.[3] After several years of careful study Büchi and co-workers proposed the structure of patchouli alcohol to correspond to 1, based on degradation studies from his earlier work, verified later by synthesis of material which corresponded to the natural authentic sample of patchouli alcohol.[4]

Proposed sequence for the synthesis of patchouli alcohol.

A serendipitous finding by Dunitz and co-workers revealed a contradictory structure. They had undertaken an X-ray analysis of the patchouli alcohol diester of chromic acid, with the objective of determining the Cr-O-C angles. In the course of their analysis they found that the X-ray evidence could not be reconciled with the proposed structure 1.[5] Instead they proposed together with Büchi the novel structure 2. The discrepancy had resulted from an unanticipated skeletal rearrangement that had occurred in the Büchi synthesis when patchoulene was treated with peroxy acid, an operation that by accident generated the correct architecture of the natural product.[6]

Actual sequence for the synthesis of patchouli alcohol.

Contains embedded [2.2.2]propellane motif.

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See also

References
  1. Deguerry, F.; Pastore, L.; Wu, S.; Clark, A.; Chappell, J.; Schalk, M. (2006). "The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases". Archives of Biochemistry and Biophysics. 454 (2): 123–136. doi:10.1016/j.abb.2006.08.006. PMID 16970904.
  2. Büchi, G.; Erickson, R. E.; Wakabyashi, N. (1961). "Terpenes. XVI. Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene". Journal of the American Chemical Society. 83: 927. doi:10.1021/ja01465a042.
  3. Simonsen, J.; Barton, D. H. R. (1952). The Terpenes. Vol. 111. Cambridge University Press, London.
  4. Büchi, G.; Macleod, W. D. (1962). "Synthesis of Patchouli Alcohol". Journal of the American Chemical Society. 84: 3205–3206. doi:10.1021/ja00875a047.
  5. Dobler, M.; Dunitz, J. D.; Gubler, B., Weber, H. P.; Büchi, G.; Padilla, O. J. (1963). "The Structure of Patchouli Alcohol". Proc. Chem. Soc. December: 383. doi:10.1039/PS9630000357.CS1 maint: multiple names: authors list (link)
  6. Nicolaou, K. C.; Snyder, S. A. (2005). "Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation". Angewandte Chemie International Edition. 44: 1012–1044. doi:10.1002/anie.200460864. PMID 15688428.
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