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Patchoulol information


Patchoulol
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
CAS Number
  • 5986-55-0 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B05588
ChEBI
  • CHEBI:7940
ChemSpider
  • 9130391
ECHA InfoCard 100.025.279 Edit this at Wikidata
EC Number
  • 227-807-2
KEGG
  • C09705
PubChem CID
  • 10955174
UNII
  • HHH8CPR1M2 checkY
CompTox Dashboard (EPA)
  • DTXSID9052266 Edit this at Wikidata
InChI
  • InChI=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
    Key: GGHMUJBZYLPWFD-CUZKYEQNSA-N
SMILES
  • O[C@@]23CC[C@@H]([C@@H]1C[C@@H](CC[C@@]12C)C3(C)C)C
Properties
Chemical formula
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)
Solubility in water
practically insoluble
Solubility in ethanol soluble
Solubility in diethyl ether soluble
Refractive index (nD)
1.5029
Hazards
Safety data sheet (SDS) 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

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.

  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.

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Patchoulol

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Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli. Patchouli oil is an important material in perfumery. The (−)-optical...

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Patchouli

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fermentation, or drying. The main chemical component of patchouli oil is patchoulol, a sesquiterpene alcohol. Leaves and twigs may be harvested several times...

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Patchoulol synthase

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Patchoulol synthase (EC 4.2.3.70) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase (patchoulol-forming). This enzyme catalyses...

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Sesquiterpene

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increasingly varied. Examples include longifolene, copaene and the alcohol patchoulol. The FPP backbone can be rearranged in several different ways and further...

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Ethanol

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Norpatchoulenol

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and thought to contribute significantly to the aroma of patchouli oil. Patchoulol Teisseire, P. (1973). "Chemistry of patchouli oil". Rivista Italiana Essenze...

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Glycerol

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Sorbitol

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Inositol

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Isopropyl alcohol

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Ethchlorvynol

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Erythritol

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Butanol

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Ethylene glycol

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Isomalt

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Xylitol

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Holton Taxol total synthesis

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compound . This epoxide can be obtained in two steps from the terpene patchoulol and also from borneol. The reaction sequence is also enantioselective...

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Cetyl alcohol

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Sugar alcohol

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Maltitol

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Benzyl alcohol

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Methanol

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Isoamyl alcohol

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