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247065

Sigma-Aldrich

(S)-cis-Verbenol

95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
18881-04-4
Molecular Weight:
152.23
Beilstein:
2206582
EC Number:
235-908-8
MDL number:
MFCD00065444
UNSPSC Code:
12352000
PubChem Substance ID:
24854847
NACRES:
NA.22

Assay

95%

form

solid

optical activity

[α]20/D −9° in chloroform
[α]20/D +10° in ethanol

optical purity

ee: ≥50% (GLC)

mp

62-65 °C (lit.)

SMILES string

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

InChI

1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9-/m0/s1

InChI key

WONIGEXYPVIKFS-YIZRAAEISA-N

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General description

(S)-cis-verbenol is an aggregation pheromone component in the bark beetles. It shows potent anti-oxidative and anti-inflammatory activities.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Ulrich Krings et al.
Journal of agricultural and food chemistry, 57(21), 9944-9950 (2009-10-13)
The enzymatic conversion of alpha-pinene to verbenols, verbenone, and minor volatile flavors was studied using submerged cultured cells, lyophilisate, and microsomal fractions of the edible basidiomycete Pleurotus sapidus . The similarity of the product range obtained by the bioconversions with
Jeremy D Allison et al.
Journal of economic entomology, 105(3), 923-929 (2012-07-21)
Stressed or damaged pine (Pinus sp.) trees in the southeastern United States are often colonized simultaneously by three southern Ips species (Coleoptera: Curculionidae: Scolytinae): small southern pine engraver, Ips avulsus (Eichhoff); sixspined ips, Ips calligraphus (Germar); and eastern fivespined ips
B Wang et al.
Bulletin of entomological research, 102(1), 71-77 (2011-07-23)
Interactions between invasive insects and their fungal associates have important effects on the behavior, reproductive success, population dynamics and evolution of the organisms involved. The red turpentine beetle (RTB), Dendroctonus valens LeConte (Coleoptera: Scolytinae), an invasive forest pest in China
Interconversion of verbenols and verbenone by identified yeasts isolated from the spruce bark beetle Ips typographus.
Leufven A, et al.
Journal of Chemical Ecology, 10(9), 1349-1361 (1984)
Martin N Andersson et al.
Journal of chemical ecology, 37(8), 899-911 (2011-07-14)
Orientation for insects in olfactory landscapes with high semiochemical diversity may be a challenging task. The partitioning of odor plumes into filaments that are interspersed with pockets of 'clean air' may help filament discrimination and upwind flight to attractive sources
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