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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:
4695-62-9
Molecular Weight:
152.23
Beilstein:
2206555
EC Number:
225-160-0
MDL number:
MFCD00070689
UNSPSC Code:
85151701
PubChem Substance ID:
329757102
NACRES:
NA.24
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grade

analytical standard

Quality Level

100

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[1][2]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ7321
BCCD4729
BCBX0771
BCBT7523

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L.A. Paquette et al.
The Journal of Organic Chemistry, 57, 3965-3965 (1992)
P. Gosselin et al.
Tetrahedron Letters, 31, 3151-3151 (1990)
Philip C Bulman Page et al.
The Journal of organic chemistry, 67(22), 7787-7796 (2002-10-26)
The first two stable enantiomerically pure chiral N-H oxaziridines, derived from camphor and fenchone, are shown to act as electrophilic sources of nitrogen upon reaction with various carbon nucleophiles. Nitrogen is transferred, together with the camphor/fenchone unit, when deprotonated esters
Boris Steuer et al.
Phytochemical analysis : PCA, 14(5), 285-289 (2003-10-01)
The aim of this study was to investigate the accuracy and transferability of near-infrared (NIR) calibrations for estimating the content and composition of the volatile fraction in fennel fruits (Foeniculum vulgare Miller) as an example of medicinal and spice plants.
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
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