Thujone

Thujone
(−)-α-Thujone	(+)-β-Thujone
	; Ball-and-stick model of (−)-α-thujone
Names
	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
CAS Number	76231-76-0 (α,β-thujone) ; 546-80-5 (α-thujone) ; 471-15-8 (β-thujone) ;
3D model (JSmol)	(α-thujone): Interactive image; (β-thujone): Interactive image;
Beilstein Reference	4660369
ChEBI	CHEBI:9577 ;
ChEMBL	ChEMBL1444078;
ChemSpider	229574 (α-thujone) ; 82583 (β-thujone) ;
ECHA InfoCard	100.013.096
EC Number	214-405-7;
IUPHAR/BPS	5344;
KEGG	C09906;
PubChem CID	261491; 11027;
UNII	86HK1QRJ4K (α,β-thujone) ; R0SQ9G0DU5 (α-thujone) ; 8ZI5R3T54Q (β-thujone) ;
CompTox Dashboard (EPA)	DTXSID20859476 ;
	InChI 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 ; 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	152.237 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)
Solubility in water	407 mg/L
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	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). verify (what is ?) Infobox references

This article includes inline links to audio files. If you have trouble playing the files, see Wikipedia Media help.

Thujone (/ˈθuːdʒoʊn/ ^ⓘ^[2]) is a ketone and a monoterpene that occurs predominantly in two diastereomeric (epimeric) forms: (−)-α-thujone and (+)-β-thujone.^[3]^[4]

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 GABA_A receptor as an antagonist. As a competitive antagonist of GABA_A 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

^ Richert, Clemens; Krupp, Felix; Frey, Wolfgang (2020). "Absolute Configuration of Small Molecules by Co-Crystallization". Angew. Chem. Int. Ed. 59 (37): 15875–15879. doi:10.1002/anie.202004992. PMC 7540501. PMID 32441841.
^ Derived from the Ancient Greek θυία, thuj(a), a kind of cedar + -ωνη, -one, feminine patronymic for a chemical relative of acetone
^ Perry NB, Anderson RE, Brennan NJ, Douglas MH, Heaney AJ, McGimpsey JA, Smallfield BM (1999). "Essential Oils from Dalmatian Sage (Salvia officinalis L.): Variations among Individuals, Plant Parts, Seasons, and Sites". J. Agric. Food Chem. 47 (5): 2048–2054. Bibcode:1999JAFC...47.2048P. doi:10.1021/jf981170m. PMID 10552494.
^ Oppolzer W, Pimm A, Stammen B, Hume WE (1997). "Palladium-Catalysed Intramolecular Cyclisations of Olefinic Propargylic Carbonates and application to the diastereoselective synthesis of enantiomerically pure (−)-α-thujone". Helv. Chim. Acta. 80 (3): 623–639. doi:10.1002/hlca.19970800302.
^ Dettling A, Grass H, Schuff A, Skopp G, Strohbeck-Kuehner P, Haffner HT (2004). "Absinthe: attention performance and mood under the influence of thujone". J. Stud. Alcohol. 65 (5): 573–81. doi:10.15288/jsa.2004.65.573. PMID 15536765.
^ Absinthe Myths Finally Laid To Rest
^ Chemical Composition of Vintage Preban Absinthe with Special Reference to Thujone, Fenchone, Pinocamphone, Methanol, Copper, and Antimony Concentrations
^ Olsen, Richard W. (2000-04-25). "Absinthe and γ-aminobutyric acid receptors". Proceedings of the National Academy of Sciences of the United States of America. 97 (9): 4417–4418. Bibcode:2000PNAS...97.4417O. doi:10.1073/pnas.97.9.4417. ISSN 0027-8424. PMC 34311. PMID 10781032.
^ Williams, Jack D.; Yazarians, Jessica A.; Almeyda, Chelcie C.; Anderson, Kristin A.; Boyce, Gregory R. (23 May 2016). "Detection of the Previously Unobserved Stereoisomers of Thujone in the Essential Oil and Consumable Products of Sage (Salvia officinalis L.) Using Headspace Solid-Phase Microextraction–Gas Chromatography–Mass Spectrometry". Journal of Agricultural and Food Chemistry. 64 (21): 4319–4326. Bibcode:2016JAFC...64.4319W. doi:10.1021/acs.jafc.6b01065. PMID 27181395.

[1] Richert, Clemens; Krupp, Felix; Frey, Wolfgang (2020). "Absolute Configuration of Small Molecules by Co-Crystallization". Angew. Chem. Int. Ed. 59 (37): 15875–15879. doi:10.1002/anie.202004992. PMC 7540501. PMID 32441841.

[2] Derived from the Ancient Greek θυία, thuj(a), a kind of cedar + -ωνη, -one, feminine patronymic for a chemical relative of acetone

[3] Perry NB, Anderson RE, Brennan NJ, Douglas MH, Heaney AJ, McGimpsey JA, Smallfield BM (1999). "Essential Oils from Dalmatian Sage (Salvia officinalis L.): Variations among Individuals, Plant Parts, Seasons, and Sites". J. Agric. Food Chem. 47 (5): 2048–2054. Bibcode:1999JAFC...47.2048P. doi:10.1021/jf981170m. PMID 10552494.

[4] Oppolzer W, Pimm A, Stammen B, Hume WE (1997). "Palladium-Catalysed Intramolecular Cyclisations of Olefinic Propargylic Carbonates and application to the diastereoselective synthesis of enantiomerically pure (−)-α-thujone". Helv. Chim. Acta. 80 (3): 623–639. doi:10.1002/hlca.19970800302.

[pmid15536765-5] Dettling A, Grass H, Schuff A, Skopp G, Strohbeck-Kuehner P, Haffner HT (2004). "Absinthe: attention performance and mood under the influence of thujone". J. Stud. Alcohol. 65 (5): 573–81. doi:10.15288/jsa.2004.65.573. PMID 15536765.

[acs-6] Absinthe Myths Finally Laid To Rest

[7] Chemical Composition of Vintage Preban Absinthe with Special Reference to Thujone, Fenchone, Pinocamphone, Methanol, Copper, and Antimony Concentrations

[:0-8] Olsen, Richard W. (2000-04-25). "Absinthe and γ-aminobutyric acid receptors". Proceedings of the National Academy of Sciences of the United States of America. 97 (9): 4417–4418. Bibcode:2000PNAS...97.4417O. doi:10.1073/pnas.97.9.4417. ISSN 0027-8424. PMC 34311. PMID 10781032.

[williams2016-9] Williams, Jack D.; Yazarians, Jessica A.; Almeyda, Chelcie C.; Anderson, Kristin A.; Boyce, Gregory R. (23 May 2016). "Detection of the Previously Unobserved Stereoisomers of Thujone in the Essential Oil and Consumable Products of Sage (Salvia officinalis L.) Using Headspace Solid-Phase Microextraction–Gas Chromatography–Mass Spectrometry". Journal of Agricultural and Food Chemistry. 64 (21): 4319–4326. Bibcode:2016JAFC...64.4319W. doi:10.1021/acs.jafc.6b01065. PMID 27181395.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]