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247065

Sigma-Aldrich

(S)-cis-Verbenol

95%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H16O
Número de CAS:
18881-04-4
Peso molecular:
152.23
Beilstein/REAXYS Number:
2206582
EC Number:
235-908-8
MDL number:
MFCD00065444
UNSPSC Code:
12352000
PubChem Substance ID:
24854847
NACRES:
NA.22

Quality Level

200

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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
SHBP0449
SHBN7440
SHBM7964
SHBM6059
SHBH6778

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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
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
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
Longwa Zhang et al.
Environmental entomology, 38(2), 472-477 (2009-04-25)
The red turpentine beetle, Dendroctonus valens LeConte (Coleoptera: Curculionidae: Scolytinae), has caused extensive mortality of Pinus tabuliformis Carrière in north central China. The electrophysiological and behavioral activities of the four bark beetle pheromones, frontalin, exo-brevicomin, trans-verbenol, and cis-verbenol, singly or
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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