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{{chembox |
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{{chembox |
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| Name = Patchoulol |
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| verifiedrevid = 406274116 |
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| ImageFile = Patchoulol.png |
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| Name = Patchoulol |
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| ImageSize = 240px |
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| ImageFile = Patchoulol.png |
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| ImageSize = 240px |
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| ImageFile1 = MinusPatchoulol-stickModel.png |
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| ImageFile1 = MinusPatchoulol-stickModel.png |
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| IUPACName = 3,4,4αβ,5,6β,7,8,8α-Octahydro-4α,8αβ,9,9-<br>tetramethyl-1,6-methanonaphthalen-1β(2H)-ol |
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| ImageName1 = |
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| OtherNames = Patchouli camphor;<br> (–)-patchoulol;<br> (1R,3R,6S,7S,8S)-patchoulol, patchouli alcohol |
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| PIN = (1''R'',4''S'',4a''S'',6''R'',8a''S'')-4,8a,9,9-Tetramethyldecahydro-1,6-methanonaphthalen-1-ol |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Patchouli camphor;<br/> (−)-Patchoulol;<br/> (1''R'',3''R'',6''S'',7''S'',8''S'')-Patchoulol;<br/> Patchouli alcohol |
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| SMILES = O23CC(1C(CC12C)C3(C)C)C |
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|Section1={{Chembox Identifiers |
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| CASNo = 5986-55-0 |
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| SMILES = O23CC(1C(CC12C)C3(C)C)C |
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| EINECS = 227-807-2 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 5986-55-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = HHH8CPR1M2 |
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| EINECS = 227-807-2 |
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| PubChem = 10955174 |
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| ChemSpiderID = 9130391 |
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| ChEBI = 7940 |
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| KEGG = C09705 |
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| 3DMet = B05588 |
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| 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 |
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| StdInChIKey = GGHMUJBZYLPWFD-CUZKYEQNSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>15</sub>H<sub>26</sub>O |
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| Formula = C<sub>15</sub>H<sub>26</sub>O |
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| MolarMass = 222.36 |
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| MolarMass = 222.36 |
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| Appearance = Hexagonal-trapezohedral crystals |
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| Appearance = white solid |
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| Density = 1.0284 |
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| Density = 1.0284 g/mL |
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| Solubility = practically insoluble |
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| Solubility = practically insoluble |
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| Solubility1 = soluble |
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| Solubility1 = soluble |
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| Solvent1 = ethanol |
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| Solvent1 = ethanol |
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| Solubility2 = soluble |
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| Solubility2 = soluble |
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| Solvent2 = diethyl ether |
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| tipo a merda que se poe no cu |
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| RefractIndex = 1.5029 |
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| Solvent2 = diethyl ether |
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| MeltingPtC = 56 |
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| RefractIndex = 1.5029 |
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| MeltingPt = 56 °C, 329 K, 133 °F<br>39-40 °C (racemic) |
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| MeltingPt_notes = (racemic) |
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| BoilingPtC = 140 |
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| BoilingPtC = 287-288 |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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<!-- | Section8 = {{Chembox Related |
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'''Patchoulol''' or '''patchouli alcohol''' (C<sub>15</sub>H<sub>26</sub>O) is a ] extracted from ] <ref>Deguerry F., Pastore L., Wu S., Clark A., Chappell J., Schalk M. The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases(2006) Archives of Biochemistry and Biophysics, 454 (2), pp. 123-136.</ref>. The (-)-] is one of the ]s responsible for the typical patchouli scent. Patchoulol is also used in the synthesis of the chemotherapy drug ]. |
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'''Patchoulol''' or '''patchouli alcohol''' (C<sub>15</sub>H<sub>26</sub>O) is a ] alcohol found in ].<ref>{{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}}</ref> Patchouli oil is an important material in perfumery. The (−)-] is one of the ]s responsible for the typical patchouli scent. Patchoulol is obtained by fermentation of leaves of ''Pogostemon cablin''.<ref name=KO>{{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 }}</ref> |
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Patchoulol is also used in the synthesis of the chemotherapy drug ].{{cn|date=November 2024}} |
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== Toxicology == |
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{{Empty section|date=July 2009}} |
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==Structure determination== |
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== See also == |
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Gal first isolated patchouli alcohol in 1869, and Montgolfier later formulated its chemical composition (correctly) as C<sub>15</sub>H<sub>26</sub>O.<ref>{{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}}</ref> Early structural investigation soon established the presence of a saturated tricyclic tertiary alcohol.<ref>{{cite book |author1=Simonsen, J. |author2=Barton, D. H. R. |title= The Terpenes |volume= 111 |publisher= Cambridge University Press, London |year= 1952}}</ref> After several years of careful degradation study, ] 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.<ref>{{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}}</ref> |
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octane motif.]] |
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However, ] and co-workers serendipitously discovered that Büchi's structure is in fact incorrect. Dunitz ''et al.'' had undertaken ] of the patchouli alcohol diester with ], 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'''.<ref>{{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}}</ref> 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 ] in Büchi's confirmatory synthesis. The rearranged molecule coincidentally exhibited the correct natural product architecture.<ref>{{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}}</ref> |
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== External links == |
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==See also== |
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==References== |
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{{Reflist}} |
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==External links== |
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