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196444

Sigma-Aldrich

(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:
2217-02-9
Molecular Weight:
154.25
Beilstein:
2038082
MDL number:
MFCD00003760
UNSPSC Code:
12352200
PubChem Substance ID:
24851760

Quality Level

100

Assay

96%

form

solid

mp

39-45 °C (lit.)

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.

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.

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

Certificates of Analysis (COA)

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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
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
M Miyazawa et al.
Xenobiotica; the fate of foreign compounds in biological systems, 37(9), 943-953 (2007-11-10)
The metabolism of (+)-fenchol was investigated in vitro using liver microsomes of rats and humans and recombinant cytochrome P450 (P450 or CYP) enzymes in insect cells in which human/rat P450 and NADPH-P450 reductase cDNAs had been introduced. The biotransformation of
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.
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