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Merck
CN

247065

(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
UNSPSC Code:
12352000
NACRES:
NA.22
PubChem Substance ID:
24854847
EC Number:
235-908-8
Beilstein/REAXYS Number:
2206582
MDL number:
MFCD00065444

Key Documents

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Product Name

(S)-cis-Verbenol, 95%

InChI key

WONIGEXYPVIKFS-YIZRAAEISA-N

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

SMILES string

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

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.)

functional group

hydroxyl

Quality Level

200

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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP0449
SHBN7440
SHBM7964
SHBM6059
SHBH6778

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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
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
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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