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Merck

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
Assay:
95%
Form:
solid

Key Documents

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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)

Quality Level

200

mp

62-65 °C (lit.)

functional group

hydroxyl

Related Categories

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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In-Young Choi et al.
Free radical research, 44(5), 541-551 (2010-03-11)
(S)-cis-verbenol, a natural metabolite from (-)-alpha-pinene of host pine tree, has been suggested to have anti-ischemic activity. However, the exact mechanism for the anti-ischemic activity of (S)-cis-verbenol remains unclear yet. In the present study, (S)-cis-verbenol reduced cerebral ischemic injury caused
T Røstelien et al.
Chemical senses, 30(5), 443-461 (2005-05-27)
Moths of the subfamily Heliothinae are suitable models for comparative studies of plant odour information encoded by the olfactory system. Here we identify and functionally classify types of olfactory receptor neurons by means of electrophysiological recordings from single receptor neurons
Marica Lindmark-Henriksson et al.
Journal of natural products, 66(3), 337-343 (2003-03-29)
alpha-Pinene, both as the pure enantiomers and as the racemate, was transformed mainly to trans-verbenol by treatment with a Picea abies suspension cell culture. These reactions were followed by a slow transformation of the verbenol to verbenone, which was not
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
Deepa S Pureswaran et al.
Die Naturwissenschaften, 95(1), 33-44 (2007-07-31)
Aggregation via pheromone signalling is essential for tree-killing bark beetles to overcome tree defenses and reproduce within hosts. Pheromone production is a trait that is linked to fitness, so high individual variation is paradoxical. One explanation is that the technique
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