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46208

Supelco

(+)-Fenchone

analytical standard

Synonym(s):

(+)-1,3,3-Trimethyl-2-norbornanone, (1S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
Molecular Weight:
152.23
Beilstein:
2206555
EC Number:
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

Assay

≥99.5% (sum of enantiomers, GC)

optical activity

[α]20/D +62±1°, neat

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.462

bp

63-65 °C/13 mmHg (lit.)

mp

5-7 °C (lit.)

density

0.945 g/mL at 20 °C (lit.)

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

SMILES string

CC1(C)[C@@H]2CC[C@@](C)(C2)C1=O

InChI

1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m1/s1

InChI key

LHXDLQBQYFFVNW-XCBNKYQSSA-N

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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

Highly purified (+)-fenchone; the keto function can be transformed in many ways

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

150.8 °F - closed cup

Flash Point(C)

66 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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P. Gosselin et al.
Tetrahedron Letters, 31, 3151-3151 (1990)
L.A. Paquette et al.
The Journal of Organic Chemistry, 57, 3965-3965 (1992)
Dirk W Lachenmeier et al.
Journal of agricultural and food chemistry, 56(9), 3073-3081 (2008-04-19)
Thirteen samples of authentic absinthe dating from the preban era (i.e., prior to 1915) were analyzed for parameters that were hypothesized as contributing to the toxicity of the spirit, including naturally occurring herbal essences (thujone, pinocamphone, fenchone), methanol, higher alcohols
Mitsuo Miyazawa et al.
Biological & pharmaceutical bulletin, 29(12), 2354-2358 (2006-12-05)
The in vitro metabolism of (+)-fenchone was examined in human liver microsomes and recombinant enzymes. Biotransformation of (+)-fenchone was investigated by gas chromatography-mass spectrometry. (+)-Fenchone was found to be oxidized to 6-exo-hydroxyfenchone, 6-endo-hydroxyfenchone and 10-hydroxyfenchone by human liver microsomal P450
Yoshio Kasashima et al.
Journal of oleo science, 58(8), 421-427 (2009-07-09)
Intramolecular etherification of 1,3-diols was investigated using iodine as a catalyst under solvent-free conditions. The reaction proceeded to completion in a heterogeneous system. Five-membered cyclic ethers were obtained by intramolecular cyclization of 1,3-diols with dehydration. A propella ether (11-oxatricyclo[4.4.3.0(1,6)]tridecane) was

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