Thujone
Group of four possible stereoisomers found in various plants: a.o., absinthe and mint / From Wikipedia, the free encyclopedia
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Thujone (/ˈθuːdʒoʊn/ ⓘ[2]) is a ketone and a monoterpene that occurs predominantly in two diastereomeric (epimeric) forms: (−)-α-thujone and (+)-β-thujone.[3][4]
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Ball-and-stick model of (−)-α-thujone[1] | |||
Names | |||
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IUPAC names
α: (1S,4R,5R)-4-Methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one β: (1S,4S,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one | |||
Other names
Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1α,4α,5α)]- α-Thujone β-Thujone Thujone, cis 3-Thujanone, (1S,4R,5R)-(−)- Thujon 3-Thujanone, (−)- l-Thujone; 4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one-, (1S,4R,5R)- 3-Thujone; cis-Thujone (Z)-Thujone (−)-Thujone; Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)- NSC 93742 1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one | |||
Identifiers | |||
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3D model (JSmol) |
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4660369 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.013.096 | ||
EC Number |
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KEGG | |||
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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Properties | |||
C10H16O | |||
Molar mass | 152.237 g·mol−1 | ||
Density | 0.92 g/cm3 (β-thujone); 0.9116 g/cm3 (α-thujone) | ||
Melting point | <25 °C | ||
Boiling point | 203 °C (397 °F; 476 K) (alpha,beta-thujone) | ||
407 mg/L | |||
Hazards | |||
GHS labelling: | |||
Warning | |||
H302 | |||
P264, P270, P301+P312, P330, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Though it is best known as a chemical compound in the spirit absinthe, it is unlikely to be responsible for absinthe's alleged stimulant and psychoactive effects due to the small quantities present.[5][6][7]
Thujone acts on the GABAA receptor as an antagonist. As a competitive antagonist of GABAA receptor, thujone alone is considered to be convulsant,[8] though by interfering with the inhibitory transmitter GABA, it may convey stimulating, mood-elevating effects at low doses.[citation needed] It is also found in perfumery as a component of several essential oils.[citation needed]
In addition to the naturally occurring (−)-α-thujone and (+)-β-thujone, two other forms are possible: (+)-α-thujone and (−)-β-thujone. In 2016, they were found in nature as well,[9] in Salvia officinalis.
- (−)-α-thujone
- (+)-α-thujone
- (+)-β-thujone
- (−)-β-thujone