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Merck
CN

94882

(1S)-(−)-Verbenone

analytical standard

Synonym(s):

(1S,5S)-2-Pinen-4-one, (1S,5S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one

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About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
1196-01-6
Molecular Weight:
150.22
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329770394
EC Number:
214-807-2
Beilstein/REAXYS Number:
1907623
MDL number:
MFCD00065445

Key Documents

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Product Name

(1S)-(−)-Verbenone, analytical standard

InChI key

DCSCXTJOXBUFGB-JGVFFNPUSA-N

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

SMILES string

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

grade

analytical standard

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

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

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
Monoterpenoid chiral building block.; Isomerization to 2(10)-pinen-4-one; Cyclopentannulation; Oxidative cleavage to pinononic acid

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

185.0 °F - closed cup

flash_point_c

85 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0408
BCCK0486
BCCD8826
BCBZ4229
BCBW2664

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G. Ohloff et al.
Helvetica Chimica Acta, 60, 1496-1496 (1977)
P.H.J. Carlsen et al.
Acta Chemica Scandinavica. Series B, 38, 501-501 (1984)
K.J. Moriarty et al.
Organometallics, 8, 1512-1512 (1989)
Deepa S Pureswaran et al.
Journal of economic entomology, 105(1), 140-148 (2012-03-17)
We collected, identified, and quantified volatiles arising from individual gallery entrances of the monogamous bark beetle Dendroctonus frontalis Zimmermann. Samples were collected while the insects were mass attacking mature loblolly pines (Pinus taeda L.) in an established infestation in western
Chung Ju et al.
Biochemical and biophysical research communications, 431(3), 484-489 (2013-01-22)
Excessive generation of free radicals is regarded as a major detrimental factor in cerebral ischemic insults. Neurons are particularly vulnerable to oxidative stress due to their limited anti-oxidant capacity. As an important source of antioxidants in the brain, astroglia are
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