WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H571396
CAS#: 546-80-5
Description: 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.
Hodoodo Cat#: H571396
Name: Thujone
CAS#: 546-80-5
Chemical Formula: C10H16O
Exact Mass: 152.12
Molecular Weight: 152.240
Elemental Analysis: C, 78.90; H, 10.59; O, 10.51
This product is not in stock, which may be available by custom synthesis.
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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:
Biological target: | |
In vitro activity: | |
In vivo activity: |
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.
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 |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
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.