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W506907

Sigma-Aldrich

(1S)-(−)-Verbenone

≥93%

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
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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Vitaly Kovalenko et al.
Chirality, 31(10), 865-869 (2019-08-09)
R/S mixture of monoterpene alcohol cis-verbenol can be separated in preparative scale by its conversion into phthalic mono-ester and subsequent crystallization of its diastereomeric salts with (R)-α-methylbenzylamine and (S)-α-methylbenzylamine. Finally, basic methanolysis of the resolved phthalic mono-esters results (S)-cis-verbenol and
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
Christopher J Fettig et al.
Journal of economic entomology, 105(1), 149-160 (2012-03-17)
Currently, techniques for managing western pine beetle, Dendroctonus brevicomis LeConte (Coleoptera: Curculionidae, Scolytinae), infestations are limited to tree removals (thinning) that reduce stand density and presumably host susceptibility, and/or the use of insecticides to protect individual trees. There continues to
Nancy E Gillette et al.
Environmental entomology, 41(6), 1575-1586 (2013-01-17)
In an attempt to improve semiochemical-based treatments for protecting forest stands from bark beetle attack, we compared push-pull versus push-only tactics for protecting lodgepole pine (Pinus contorta Douglas ex Loudon) and whitebark pine (Pinus albicaulis Engelm.) stands from attack by
Zulfa Yoosuf-Aly et al.
Chemical communications (Cambridge, England), 48(56), 7040-7042 (2012-06-12)
The enzyme-guided asymmetric synthesis of (+)-verbenone from geranyl diphosphate in a simple two-step, one pot transformation highlights the potential of chemoenzymatic procedures for the generation of high-value terpenoids.
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