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Sigma-Aldrich

(−)-α-Thujone

≥96.0% (GC)

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Synonym(s):
(-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
Empirical Formula (Hill Notation):
C10H16O
Molecular Weight:
152.23
Beilstein:
4660369
EC Number:
208-912-2
MDL number:
MFCD00001313
PubChem Substance ID:
57653336
NACRES:
NA.22

Assay

≥96.0% (GC)

form

liquid

optical activity

[α]20/D −19.0±2.0°, neat

refractive index

n20/D 1.450

density

0.914 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2

InChI

1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1

InChI key

USMNOWBWPHYOEA-MRTMQBJTSA-N

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General description

(-)-α-Thujone, a monoterpene ketone found in the essential oil of Thuja occidentalis, shows potent antitumorigenic effect.

Biochem/physiol Actions

GABAA receptor antagonist.

Other Notes

Chiral building block

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

147.2 °F - closed cup

Flash Point(C)

64 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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J.P. Kutney et al.
Canadian Journal of Chemistry, 72, 1570-1570 (1994)
M J Eadie
The journal of the Royal College of Physicians of Edinburgh, 39(1), 73-78 (2009-10-17)
Absinthe is an alcoholic liquor containing extracts from the wormwood plant. It was widely consumed in France in the late nineteenth century. Its production was banned in 1915, partly because it was thought to cause neurological disturbances, including mental changes
K S Siveen et al.
International immunopharmacology, 11(12), 1967-1975 (2011-09-03)
Thujone, a naturally occurring monoterpene, was found to enhance the total WBC count, bone marrow cellularity, number of α-esterase positive cells, number of plaque forming cells in spleen and circulating antibody titer in Balb/c mice (1mg/kg body weight, intraperitoneally for
Hakam Alkhateeb et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 299(3), R804-R812 (2010-06-25)
Thujone is thought to be the main constituent of medicinal herbs that have antidiabetic properties. Therefore, we examined whether thujone ameliorated palmitate-induced insulin resistance in skeletal muscle. Soleus muscles were incubated for < or =12 h without or with palmitate
Haouari Mohsen et al.
Molecules (Basel, Switzerland), 14(4), 1585-1594 (2009-04-23)
The composition of the essential oil hydrodistilled from the aerial parts of 18 individual Artemisia herba-alba Asso. plants collected in southern Tunisia was determined by GC and GCMS analysis. The oil yield varied between 0.68% v/w and 1.93% v/w. One
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