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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
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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

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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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
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
R Agrawal et al.
Biotechnology and bioengineering, 63(2), 249-252 (1999-04-01)
Variants of Aspergillus sp. and Penicillium sp. obtained after treatment with colchicine, ethyl methanesulphonate (EMS), or ultraviolet (UV) irradiation indicated varying levels of significant increases in their efficiency to transform alpha-pinene to verbenol. In case of Aspergillus sp. the UV-induced
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Global Trade Item Number

SKUGTIN
247065-5G04061825883847
247065-25G04061832718910