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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

196444-5KG:
196444-VAR:
196444-500G:
196444-BULK:
196444-100G:
196444-5G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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