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W506907

Sigma-Aldrich

(1S)-(−)-Verbenone

≥93%

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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
UNSPSC Code:
12164502
PubChem Substance ID:
24902029
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009

Assay

≥93%

optical activity

[α]20/D −140°, c = 10 in ethanol

refractive index

n20/D 1.496 (lit.)

bp

227-228 °C (lit.)

density

0.975 g/mL at 20 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

camphoraceous; minty; spicy

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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Related Categories

Application

  • Anti-Inflammatory and Antinociceptive Activities of the Essential Oil of Tagetes parryi A. Gray (Asteraceae) and Verbenone.: This article reports on the anti-inflammatory and pain-relief effects of (1S)-(−)-Verbenone as part of the essential oil of Tagetes parryi, suggesting potential therapeutic applications for pain management and inflammation (González-Velasco et al., 2022).

Disclaimer

For R&D or non-EU Food use. Not for retail sale.

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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.
Michael Pescheck et al.
Journal of industrial microbiology & biotechnology, 36(6), 827-836 (2009-03-27)
A closed gas loop bioprocess was developed to improve fungal biotransformation of monoterpenes. By circulating monoterpene-saturated process gas, the evaporative loss of the volatile precursor from the medium during the biotransformation was avoided. Penicillium solitum, isolated from kiwi, turned out
Christopher J Fettig et al.
Journal of economic entomology, 105(5), 1668-1680 (2012-11-20)
The western pine beetle, Dendroctonus brevicomis LeConte (Coleoptera: Curculionidae, Scolytinae), is a major cause of ponderosa pine, Pinus ponderosa Douglas ex Lawson, mortality in much of western North America. We review several years of research that led to the identification
Dorothea Kaufmann et al.
The Journal of pharmacy and pharmacology, 63(10), 1368-1371 (2011-09-09)
Inhibition of acetylcholinesterase (AChE) is a common treatment for early stages of the most general form of dementia, Alzheimer's disease. In this study selected components of essential oils, which carry a variety of important functional groups, were tested for their
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