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MedKoo Cat#: 571396 | Name: Thujone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Thujone is a major component of absinthe drink. It has neurotoxic properties. It inhibits the gamma-aminobutyric acid A (GABA(A)) receptor causing excitation and convulsions in a dose-dependent manner. It may have potential to treat osteoporosis.

Chemical Structure

Thujone
Thujone
CAS#546-80-5

Theoretical Analysis

MedKoo Cat#: 571396

Name: Thujone

CAS#: 546-80-5

Chemical Formula: C10H16O

Exact Mass: 152.1201

Molecular Weight: 152.24

Elemental Analysis: C, 78.90; H, 10.59; O, 10.51

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Thujone; Absinthol
IUPAC/Chemical Name
1-Isopropyl-4-methylbicyclo(3.1.0)hexan-3-one
InChi Key
USMNOWBWPHYOEA-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3
SMILES Code
O=C1CC2(C(C)C)CC2C1C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 152.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Pelkonen O, Abass K, Wiesner J. Thujone and thujone-containing herbal medicinal and botanical products: toxicological assessment. Regul Toxicol Pharmacol. 2013 Feb;65(1):100-7. doi: 10.1016/j.yrtph.2012.11.002. Epub 2012 Nov 28. Review. PubMed PMID: 23201408. 2: Küpeli Akkol E, İlhan M, Ayşe Demirel M, Keleş H, Tümen I, Süntar İ. Thuja occidentalis L. and its active compound, α-thujone: Promising effects in the treatment of polycystic ovary syndrome without inducing osteoporosis. J Ethnopharmacol. 2015 Jun 20;168:25-30. doi: 10.1016/j.jep.2015.03.029. Epub 2015 Mar 27. PubMed PMID: 25818694. 3: Rivera EM, Cid MP, Zunino P, Baiardi G, Salvatierra NA. Central α- and β-thujone: similar anxiogenic-like effects and differential modulation on GABAA receptors in neonatal chicks. Brain Res. 2014 Mar 25;1555:28-35. doi: 10.1016/j.brainres.2014.01.039. Epub 2014 Jan 30. PubMed PMID: 24486357. 4: Zhou Y, Liu JQ, Zhou ZH, Lv XT, Chen YQ, Sun LQ, Chen FX. Enhancement of CD3AK cell proliferation and killing ability by α-Thujone. Int Immunopharmacol. 2016 Jan;30:57-61. doi: 10.1016/j.intimp.2015.11.027. Epub 2015 Dec 1. PubMed PMID: 26655741. 5: Williams JD, Yazarians JA, Almeyda CC, Anderson KA, Boyce GR. 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. J Agric Food Chem. 2016 Jun 1;64(21):4319-26. doi: 10.1021/acs.jafc.6b01065. Epub 2016 May 23. PubMed PMID: 27181395. 6: Gesell A, Blaukopf M, Madilao L, Yuen MM, Withers SG, Mattsson J, Russell JH, Bohlmann J. The gymnosperm cytochrome P450 CYP750B1 catalyzes stereospecific monoterpene hydroxylation of (+)-sabinene in thujone biosynthesis in western redcedar. Plant Physiol. 2015 May;168(1):94-106. doi: 10.1104/pp.15.00315. Epub 2015 Mar 31. PubMed PMID: 25829465; PubMed Central PMCID: PMC4424034. 7: Czyzewska MM, Mozrzymas JW. Monoterpene α-thujone exerts a differential inhibitory action on GABA(A) receptors implicated in phasic and tonic GABAergic inhibition. Eur J Pharmacol. 2013 Feb 28;702(1-3):38-43. doi: 10.1016/j.ejphar.2013.01.032. Epub 2013 Jan 31. PubMed PMID: 23376563. 8: Creed C, Mollhagen A, Mollhagen N, Pszczolkowski MA. Artemisia arborescens "Powis Castle" extracts and α-thujone prevent fruit infestation by codling moth neonates. Pharm Biol. 2015;53(10):1458-64. doi: 10.3109/13880209.2014.985796. Epub 2015 Apr 8. PubMed PMID: 25853962. 9: Waidyanatha S, Johnson JD, Hong SP, Robinson VG, Gibbs S, Graves SW, Hooth MJ, Smith CS. Toxicokinetics of α-thujone following intravenous and gavage administration of α-thujone or α- and β-thujone mixture in male and female F344/N rats and B6C3F1 mice. Toxicol Appl Pharmacol. 2013 Sep 1;271(2):216-28. doi: 10.1016/j.taap.2013.05.001. Epub 2013 May 10. PubMed PMID: 23669748. 10: Nikolić B, Vasilijević B, Mitić-Ćulafić D, Vuković-Gačić B, Knežević-Vukćević J. Comparative study of genotoxic, antigenotoxic and cytotoxic activities of monoterpenes camphor, eucalyptol and thujone in bacteria and mammalian cells. Chem Biol Interact. 2015 Dec 5;242:263-71. doi: 10.1016/j.cbi.2015.10.012. Epub 2015 Oct 19. PubMed PMID: 26482939. 11: El Montassir D, Aamouche A, Vanthuyne N, Jean M, Vanloot P, Taourirte M, Dupuy N, Roussel C. Attempts to separate (-)-α-thujone, (+)-β-thujone epimers from camphor enantiomers by enantioselective HPLC with polarimetric detection. J Sep Sci. 2013 Mar;36(5):832-9. doi: 10.1002/jssc.201200907. Epub 2013 Feb 4. PubMed PMID: 23378105. 12: Dybowski MP, Dawidowicz AL. The determination of α- and β-thujone in human serum - Simple analysis of absinthe congener substance. Forensic Sci Int. 2016 Feb;259:188-92. doi: 10.1016/j.forsciint.2015.12.015. Epub 2015 Dec 19. PubMed PMID: 26773227. 13: Abass K, Reponen P, Mattila S, Pelkonen O. Metabolism of α-thujone in human hepatic preparations in vitro. Xenobiotica. 2011 Feb;41(2):101-11. doi: 10.3109/00498254.2010.528066. Epub 2010 Nov 18. PubMed PMID: 21087116. 14: Siveen KS, Kuttan G. Augmentation of humoral and cell mediated immune responses by Thujone. Int Immunopharmacol. 2011 Dec;11(12):1967-75. doi: 10.1016/j.intimp.2011.08.006. Epub 2011 Aug 30. PubMed PMID: 21884824. 15: Torres A, Vargas Y, Uribe D, Carrasco C, Torres C, Rocha R, Oyarzún C, San Martín R, Quezada C. Pro-apoptotic and anti-angiogenic properties of the α /β-thujone fraction from Thuja occidentalis on glioblastoma cells. J Neurooncol. 2016 May;128(1):9-19. doi: 10.1007/s11060-016-2076-2. Epub 2016 Feb 22. PubMed PMID: 26900077. 16: Siveen KS, Kuttan G. Thujone inhibits lung metastasis induced by B16F-10 melanoma cells in C57BL/6 mice. Can J Physiol Pharmacol. 2011 Oct;89(10):691-703. doi: 10.1139/y11-067. Epub 2011 Sep 9. PubMed PMID: 21905822. 17: Bielenberg J. [Thujone]. Med Monatsschr Pharm. 2007 Sep;30(9):322-6. Review. German. PubMed PMID: 17912872. 18: Lachenmeier DW, Walch SG. The choice of thujone as drug for diabetes. Nat Prod Res. 2011 Dec;25(20):1890-2. doi: 10.1080/14786419.2011.622279. Epub 2011 Oct 11. PubMed PMID: 21988529. 19: Szczot M, Czyzewska MM, Appendino G, Mozrzymas JW. Modulation of GABAergic synaptic currents and current responses by α-thujone and dihydroumbellulone. J Nat Prod. 2012 Apr 27;75(4):622-9. doi: 10.1021/np200863q. Epub 2012 Feb 24. PubMed PMID: 22364543. 20: National Toxicology Program. Toxicology and carcinogenesis studies of alpha,beta-thujone (CAS No. 76231-76-0) in F344/N rats and B6C3F1 mice (gavage studies). Natl Toxicol Program Tech Rep Ser. 2011 Nov;(570):1-260. PubMed PMID: 22127327.

View History

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