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247065

Sigma-Aldrich

(S)-cis-Verbenol

95%

Sinonimo/i:

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

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CHF 127.00
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CHF 406.00

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5 G
CHF 127.00
25 G
CHF 406.00

About This Item

Formula empirica (notazione di Hill):
C10H16O
Numero CAS:
Peso molecolare:
152.23
Beilstein:
2206582
Numero CE:
Numero MDL:
Codice UNSPSC:
12352000
ID PubChem:
NACRES:
NA.22

CHF 127.00


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Saggio

95%

Stato

solid

Attività ottica

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

Purezza ottica

ee: ≥50% (GLC)

Punto di fusione

62-65 °C (lit.)

Gruppo funzionale

hydroxyl

Stringa SMILE

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
WONIGEXYPVIKFS-YIZRAAEISA-N

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Descrizione generale

(S)-cis-verbenol is an aggregation pheromone component in the bark beetles.[1][2] It shows potent anti-oxidative and anti-inflammatory activities.[3]

Pittogrammi

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Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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J O Levin et al.
International archives of occupational and environmental health, 63(8), 571-573 (1992-01-01)
The renal elimination of verbenols after experimental exposure to (+) and (-)alpha-pinene was studied in humans following exposure to 10, 225, and 450 mg.m-3 terpene in an exposure chamber. The pulmonary uptake was about 60%. About 8% was eliminated unchanged
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
P J Rice et al.
Journal of economic entomology, 87(5), 1172-1179 (1994-10-01)
House flies, Musca domestica (L.), and their eggs were treated with 22 monoterpenoids to determine the topical, fumigant, and ovicidal activity of each compound. Fumigant activity of 14 monoterpenoids were examined further using red flour beetles, Tribolium castaneum (Herbst). Third-instar
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
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

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