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Fenchol

Fenchol or 1,3,3-trimethyl-2-norbornanol is a monoterpenoid and an isomer of borneol. It is a colorless or white solid. It occurs widely in nature.

Fenchol[1]

(1R)-endo-(+)-Fenchol
Names
IUPAC name
(1R,2R,4S)-1,3,3-Trimethyl-2-norbornanol
Other names
Fenchyl alcohol
Identifiers
  • 1632-73-1 (unspecified isomer) Y
  • 2217-02-9 ((1R)-endo-(+))
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL3188732
ECHA InfoCard 100.015.127
  • 15406 (unspecified isomer)
  • 6997371 ((1R)-endo-(+))
UNII
  • 410Q2GK1HF
  • DTXSID1041970
  • InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1
    Key: IAIHUHQCLTYTSF-OYNCUSHFSA-N
  • CC1(C2CCC(C2)(C1O)C)C
Properties
C10H18O
Molar mass 154.253 g·mol−1
Density 0.942 g/cm3
Melting point 39 to 45 °C (102 to 113 °F; 312 to 318 K)
Boiling point 201 °C (394 °F; 474 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

The naturally occurring enantiomere (1R)-endo-(+)-fenchol is used extensively in perfumery. Fenchol gives basil its characteristic scent,[2][3] and comprises 15.9% of the volatile oils of some species of Aster.[4]

It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate.[5]

Oxidation of fenchol gives fenchone.

References edit

  1. ^ Datasheet at chemexper.com
  2. ^ "FES - (-)-endo-fenchol synthase, chloroplastic precursor - Ocimum basilicum (Sweet basil) - FES gene & protein". www.uniprot.org.
  3. ^ Kotan, Recep; Kordali, Saban; Cakir, Ahmet (August 2007). "Screening of antibacterial activities of twenty-one oxygenated monoterpenes". Zeitschrift für Naturforschung C. 62 (7–8): 507–513. doi:10.1515/znc-2007-7-808. PMID 17913064.
  4. ^ Matasyoh, Josphat C.; Kiplimo, Joyce J.; Karubiu, Nicholas M.; Hailstorks, Tiffany P. (2006). "Chemical composition and antimicrobial activity of essential oil of Tarchonanthus camphoratus". Food Chemistry. 101 (3): 1183–1187. doi:10.1016/j.foodchem.2006.03.021.
  5. ^ Satterwhite, D. M.; Wheeler, C. J.; Croteau, R. (15 November 1985). "Biosynthesis of monoterpenes. Enantioselectivity in the Enzymatic Cyclization of Linalyl Pyrophosphate to (-)-endo-Fenchol". The Journal of Biological Chemistry. 260 (26): 13901–8. doi:10.1016/S0021-9258(17)38661-1. PMID 4055764.

External links edit

  • 3D-image

fenchol, trimethyl, norbornanol, monoterpenoid, isomer, borneol, colorless, white, solid, occurs, widely, nature, endo, names, iupac, name, trimethyl, norbornanol, other, names, fenchyl, alcohol, identifiers, number, 1632, unspecified, isomer, y2217, endo, mod. Fenchol or 1 3 3 trimethyl 2 norbornanol is a monoterpenoid and an isomer of borneol It is a colorless or white solid It occurs widely in nature Fenchol 1 1R endo Fenchol Names IUPAC name 1R 2R 4S 1 3 3 Trimethyl 2 norbornanol Other names Fenchyl alcohol Identifiers CAS Number 1632 73 1 unspecified isomer Y2217 02 9 1R endo 3D model JSmol Interactive image ChEMBL ChEMBL3188732 ECHA InfoCard 100 015 127 PubChem CID 15406 unspecified isomer 6997371 1R endo UNII 410Q2GK1HF CompTox Dashboard EPA DTXSID1041970 InChI InChI 1S C10H18O c1 9 2 7 4 5 10 3 6 7 8 9 11 h7 8 11H 4 6H2 1 3H3 t7 8 10 m0 s1Key IAIHUHQCLTYTSF OYNCUSHFSA N SMILES CC1 C2CCC C2 C1O C C Properties Chemical formula C 10H 18O Molar mass 154 253 g mol 1 Density 0 942 g cm3 Melting point 39 to 45 C 102 to 113 F 312 to 318 K Boiling point 201 C 394 F 474 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references The naturally occurring enantiomere 1R endo fenchol is used extensively in perfumery Fenchol gives basil its characteristic scent 2 3 and comprises 15 9 of the volatile oils of some species of Aster 4 It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate 5 Oxidation of fenchol gives fenchone References edit Datasheet at chemexper com FES endo fenchol synthase chloroplastic precursor Ocimum basilicum Sweet basil FES gene amp protein www uniprot org Kotan Recep Kordali Saban Cakir Ahmet August 2007 Screening of antibacterial activities of twenty one oxygenated monoterpenes Zeitschrift fur Naturforschung C 62 7 8 507 513 doi 10 1515 znc 2007 7 808 PMID 17913064 Matasyoh Josphat C Kiplimo Joyce J Karubiu Nicholas M Hailstorks Tiffany P 2006 Chemical composition and antimicrobial activity of essential oil of Tarchonanthus camphoratus Food Chemistry 101 3 1183 1187 doi 10 1016 j foodchem 2006 03 021 Satterwhite D M Wheeler C J Croteau R 15 November 1985 Biosynthesis of monoterpenes Enantioselectivity in the Enzymatic Cyclization of Linalyl Pyrophosphate to endo Fenchol The Journal of Biological Chemistry 260 26 13901 8 doi 10 1016 S0021 9258 17 38661 1 PMID 4055764 External links edit3D image Retrieved from https en wikipedia org w index php title Fenchol amp oldid 1068647134, wikipedia, wiki, book, books, library,

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