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Supelco

(1S)-(−)-Verbenone

analytical standard

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Synonym(s):
(1S,5S)-2-Pinen-4-one, (1S,5S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one
Empirical Formula (Hill Notation):
C10H14O
CAS Number:
1196-01-6
Molecular Weight:
150.22
Beilstein:
1907623
EC Number:
214-807-2
MDL number:
MFCD00065445
PubChem Substance ID:
329770394
NACRES:
NA.24

grade

analytical standard

Quality Level

100

Assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D −170±12°, neat

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

refractive index

n20/D 1.496 (lit.)
n20/D 1.497

bp

227-228 °C (lit.)

density

0.975 g/mL at 20 °C (lit.)

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

storage temp.

2-8°C

SMILES string

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

InChI

1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m0/s1

InChI key

DCSCXTJOXBUFGB-JGVFFNPUSA-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

Monoterpenoid chiral building block.; Isomerization to 2(10)-pinen-4-one; Cyclopentannulation; Oxidative cleavage to pinononic acid

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Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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K.J. Moriarty et al.
Organometallics, 8, 1512-1512 (1989)
P.H.J. Carlsen et al.
Acta Chemica Scandinavica. Series B, 38, 501-501 (1984)
G. Ohloff et al.
Helvetica Chimica Acta, 60, 1496-1496 (1977)
R A Progar et al.
Journal of economic entomology, 106(1), 221-228 (2013-03-02)
Mountain pine beetle, Dendroctonus ponderosae Hopkins (Coleoptera: Curculionidae: Scolytinae), is among the primary causes of mature lodgepole pine, Pinus contorta variety latifolia mortality. Verbenone is the only antiaggregant semiochemical commercially available for reducing mountain pine beetle infestation of lodgepole pine.
Mitsuo Miyazawa et al.
Drug metabolism and disposition: the biological fate of chemicals, 31(8), 1049-1053 (2003-07-18)
(-)-Verbenone, a monoterpene bicyclic ketone, is a component of the essential oil from rosemary species such as Rosmarinus officinalis L., Verbena triphylla, and Eucalyptus globulus and is used for an herb tea, a spice, and a perfume. In this study
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