Thujone

(−)-α-Thujone

(+)-β-Thujone

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
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

CAS Number

76231-76-0 (α,β-thujone)^N
546-80-5 (α-thujone)^N
471-15-8 (β-thujone)^N

3D model (Jmol)

(α-thujone): Interactive image
(β-thujone): Interactive image

ChEBI

CHEBI:9577^Y

ChemSpider

229574 (α-thujone)^Y
82583 (β-thujone)^Y

261491
11027

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^Y

Key: USMNOWBWPHYOEA-MRTMQBJTSA-N^Y
InChI=1/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

Key: USMNOWBWPHYOEA-MRTMQBJTBZ
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

Key: USMNOWBWPHYOEA-MRTMQBJTSA-N

SMILES

(α-thujone): O=C1[C@H](C)[C@@H]2[C@](C(C)C)(C1)C2
(β-thujone): C[C@@H]([C@@H](C2)[C@]2([C@@H](C)C)C1)C1=O

Properties

Chemical formula

C₁₀H₁₆O

Molar mass

152.24 g·mol⁻¹

Density

0.92 g/cm³ (β-thujone)

Melting point

<25 °C

Boiling point

201 °C (394 °F; 474 K) (β-thujone)

Solubility in water

407 mg/L

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Thujone (ⁱ/ˈθuːdʒoʊn/) is a ketone and a monoterpene that occurs naturally in two diastereomeric forms: (−)-α-thujone and (+)-β-thujone. It has a menthol odor. Though it is best known as a chemical compound in the spirit absinthe, which contains only small quantities of thujone, it is unlikely to be responsible for absinthe's alleged psychedelic effects. Thujone acts on GABA and as a component of several essential oils, is also used in perfumery.

In addition to the naturally occurring (−)-α-thujone and (+)-β-thujone, two other enantiomeric forms are possible: (+)-α-thujone and (−)-β-thujone:

(−)-α-thujone

(+)-α-thujone

(+)-β-thujone

(−)-β-thujone

Thujone is found in a number of plants, such as arborvitae (genus Thuja, hence the derivation of the name), Nootka cypress, some junipers, mugwort, oregano, common sage, tansy, and wormwood, most notably grand wormwood (Artemisia absinthium), usually as a mix of isomers in a 1:2 ratio. It is also found in various species of Mentha (mint).

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