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Merck
CN

46198

(+)-Fenchol

analytical standard

Synonym(s):

(1R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol, Fenchyl alcohol

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
2217-02-9
Molecular Weight:
154.25
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329757098
MDL number:
MFCD00003760
Beilstein/REAXYS Number:
2038082

Key Documents

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Product Name

(+)-Fenchol, analytical standard

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

SMILES string

CC1(C)[C@H]2CC[C@](C)(C2)[C@H]1O

InChI key

IAIHUHQCLTYTSF-OYNCUSHFSA-N

grade

analytical standard

assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D +11.0±0.5°, c = 10% in ethanol

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

bp

201-202 °C (lit.)

mp

43-46 °C

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Other Notes

Chiral building block

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

165.2 °F - closed cup

flash_point_c

74 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB9706
BCBW2671
BCBR2430V

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A.A. van der Zeijden et al.
Synthesis, 847-847 (1996)
Y. Yuasa et al.
Tetrahedron, 48, 3473-3473 (1992)
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
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