patchoulol
{{chembox
| Watchedfields = changed
| verifiedrevid = 406274116
| Name = Patchoulol
| ImageFile = Patchoulol.png
| ImageSize = 240px
| ImageName =
| ImageFile1 = MinusPatchoulol-stickModel.png
| ImageSize1 =
| ImageName1 =
| PIN = (1R,4S,4aS,6R,8aS)-4,8a,9,9-Tetramethyldecahydro-1,6-methanonaphthalen-1-ol
| OtherNames = Patchouli camphor;
(−)-Patchoulol;
(1R,3R,6S,7S,8S)-Patchoulol;
Patchouli alcohol
|Section1={{Chembox Identifiers
| SMILES = O[C@@]23CC[C@@H]([C@@H]1C[C@@H](CC[C@@]12C)C3(C)C)C
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 5986-55-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = HHH8CPR1M2
| EINECS = 227-807-2
| PubChem = 10955174
| ChemSpiderID = 9130391
| ChEBI = 7940
| KEGG = C09705
| 3DMet = B05588
| StdInChI=1S/C15H26O/c1-10-5-8-15(16)13(2,3)11-6-7-14(15,4)12(10)9-11/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m0/s1
| StdInChIKey = GGHMUJBZYLPWFD-CUZKYEQNSA-N
}}
|Section2={{Chembox Properties
| Formula = C15H26O
| MolarMass = 222.36
| Appearance = white solid
| Density = 1.0284 g/mL
| Solubility = practically insoluble
| Solubility1 = soluble
| Solvent1 = ethanol
| Solubility2 = soluble
| Solvent2 = diethyl ether
| RefractIndex = 1.5029
| MeltingPtC = 56
| MeltingPt_notes = (racemic)
| BoilingPtC = 287-288
| pKa =
| Viscosity =
| Dipole =
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://www.lluche.com/eng/pdf/01185QQQQL_IN.pdf External MSDS]
}}
}}
Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli.{{cite journal |author1=Deguerry, F. |author2=Pastore, L. |author3=Wu, S. |author4=Clark, A. |author5=Chappell, J. |author6=Schalk, M. |title= The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases |journal= Archives of Biochemistry and Biophysics |year= 2006 |volume= 454 |issue= 2 |pages= 123–136 |doi= 10.1016/j.abb.2006.08.006 |pmid= 16970904}} Patchouli oil is an important material in perfumery.{{Cite web |title=Духи с запахом пачулей - Лучшие парфюмы с пачулями - Описания духов с ароматом пачулей - Парфюмерия с пачулями. |url=https://duhipatchouli.ru/ |access-date=2025-04-21 |website=duhipatchouli.ru}} The (−)-optical isomer is one of the organic compounds responsible for the typical patchouli scent. Patchoulol is obtained by fermentation of leaves of Pogostemon cablin.{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}
Patchoulol is also used in the synthesis of the chemotherapy drug Taxol.{{cn|date=November 2024}}
Structure determination
Gal first isolated patchouli alcohol in 1869, and Montgolfier later formulated its chemical composition (correctly) as C15H26O.{{cite journal |author1=Büchi, G. |author2=Erickson, R. E. |author3=Wakabyashi, N. |title= Terpenes. XVI. Constitution of Patchouli Alcohol and Absolute Configuration of Cedrene |journal= Journal of the American Chemical Society |year= 1961 |volume= 83 |issue=4 |pages= 927–938 |doi= 10.1021/ja01465a042}} Early structural investigation soon established the presence of a saturated tricyclic tertiary alcohol.{{cite book |author1=Simonsen, J. |author2=Barton, D. H. R. |title= The Terpenes |volume= 111 |publisher= Cambridge University Press, London |year= 1952}} After several years of careful degradation study, Büchi and co-workers proposed that patchouli alcohol had the structure 1. A subsequent synthesis of material which corresponded to an authentic sample of natural patchouli alcohol appeared to verify Büchi's proposal.{{cite journal |author1=Büchi, G. |author2=Macleod, W. D. |title= Synthesis of Patchouli Alcohol |journal= Journal of the American Chemical Society |year= 1962 |volume= 84 |issue=16 |pages= 3205–3206 |doi= 10.1021/ja00875a047}}
File:Proposed sequence patchouli alcohol.png
File:actual sequence patchouli alcohol.png
However, Dunitz and co-workers serendipitously discovered that Büchi's structure is in fact incorrect. Dunitz et al. had undertaken X-ray analysis of the patchouli alcohol diester with chromic 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" structure 1.{{cite journal |author= Dobler, M. |author2= Dunitz, J. D. |author3= Gubler, B. |author4= Weber, H. P. |author5= Büchi, G. |author6= Padilla, O. J. |name-list-style=amp |title= The Structure of Patchouli Alcohol |journal= Proc. Chem. Soc. |year= 1963 |volume= December |pages= 383 |doi= 10.1039/PS9630000357}} In a joint paper with Büchi, they collectively proposed that patchouli alcohol in fact had the novel structure 2. The discrepancy had resulted from an unanticipated skeletal rearrangement when patchoulene was treated with peroxy acid in Büchi's confirmatory synthesis. The rearranged molecule coincidentally exhibited the correct natural product architecture.{{cite journal |author1=Nicolaou, K. C. |author2=Snyder, S. A. |title= Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation |journal= Angewandte Chemie International Edition |year= 2005 |volume= 44 |issue=7 |pages= 1012–1044 |doi= 10.1002/anie.200460864 |pmid=15688428}}
See also
References
{{Reflist}}
External links
- [http://www.leffingwell.com/chirality/patchoulol.htm Chime 3D representation]