196444
(1R)-endo-(+)-Fenchyl alcohol
96%
Synonym(s):
(+)-Fenchol, (1R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol, 1,3,3-Trimethyl-2-norbornanol, Fenchyl alcohol
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About This Item
Empirical Formula (Hill Notation):
C10H18O
CAS Number:
Molecular Weight:
154.25
Beilstein:
2038082
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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Quality Level
Assay
96%
form
solid
mp
39-45 °C (lit.)
functional group
hydroxyl
SMILES string
CC1(C)[C@H]2CC[C@](C)(C2)[C@H]1O
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
InChI key
IAIHUHQCLTYTSF-OYNCUSHFSA-N
General description
(1R)-endo-(+)-Fenchyl alcohol is a bicyclic monoterpenoid that contains a fenchane skeleton. It is a commonly used volatile compound in fragrances and flavoring agents.[1]
Application
(1R)-endo-(+)-Fenchyl alcohol can be used to prepare other terpenoids such as (+)-(1R,2S)-10-hydroxyfenchol, (+)-(1R,2R,3S)-8-hydroxyfenchol, (-)-(1S,2S,6S)-6-exo-hydroxyfenchol, and (-)-(1R,2R,3R)-9-hydroxyfenchol.[1]
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
165.2 °F - closed cup
Flash Point(C)
74 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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D M Satterwhite et al.
The Journal of biological chemistry, 260(26), 13901-13908 (1985-11-15)
The conversion of geranyl pyrophosphate to (-)-endo-fenchol is considered to proceed by the initial isomerization of the substrate to (-)-(3R)-linalyl pyrophosphate and the subsequent cyclization of this bound intermediate. To test this stereochemical scheme, phosphatase-free preparations of (-)-endo-fenchol cyclase from
D Yang et al.
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 22(3), 128-131 (2003-02-11)
The essential oil isolated from the dried leaves of Lindera communis was analyzed by means of gas chromatography-mass(GC-MS) technique, the structures of 23 chemical components were identified from it in total, among these, (-)-spathulenol(relative content 22.50%), endo-1,3,3-trimethyl-2-norbornanol, acetate (10.06%), caryophyllene
R Croteau et al.
The Journal of biological chemistry, 263(30), 15449-15453 (1988-10-25)
The conversion of geranyl pyrophosphate to (-)-endo-fenchol is considered to proceed by the initial isomerization of the substrate to (-)-(3R)-linalyl pyrophosphate and the subsequent cyclization of this bound intermediate. Incubation of (1R)-[2-14C,1-3H]- and (1S)-[2-14C,1-3H]geranyl pyrophosphate with a preparation of (-)-endo-fenchol
S P Bhatia et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 46 Suppl 11, S157-S159 (2008-07-22)
A toxicologic and dermatologic review of fenchyl alcohol when used as a fragrance ingredient is presented.
Sergio Abbate et al.
Chirality, 21 Suppl 1, E242-E252 (2009-11-21)
The first well documented experiments of Near Infrared Vibrational Circular Dichroism (NIR-VCD) were performed around 1975. We review the thirty year history of NIR-VCD, encompassing both instrumental development and theoretical/computational methods that allow interpretation of experimental spectra, harvesting useful structural
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