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MedKoo Cat#: 581009 | Name: 2-ATHBI
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Description:

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

2-ATHBI, also known as 2-Acetyl-4-tetrahydroxybutyl Imidazole or THI, is an inhibitor of S1P lyase.

Chemical Structure

2-ATHBI
2-ATHBI
CAS#94944-70-4

Theoretical Analysis

MedKoo Cat#: 581009

Name: 2-ATHBI

CAS#: 94944-70-4

Chemical Formula: C9H14N2O5

Exact Mass: 230.0903

Molecular Weight: 230.22

Elemental Analysis: C, 46.95; H, 6.13; N, 12.17; O, 34.75

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
THI, 2-Acetyl-4-tetrahydroxybutyl Imidazole; 2-ATHBI.
IUPAC/Chemical Name
1-[5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl]-ethanone
InChi Key
CQSIXFHVGKMLGQ-BWZBUEFSSA-N
InChi Code
InChI=1S/C9H14N2O5/c1-4(13)9-10-2-5(11-9)7(15)8(16)6(14)3-12/h2,6-8,12,14-16H,3H2,1H3,(H,10,11)/t6-,7-,8-/m1/s1
SMILES Code
CC(C1=NC=C([C@@H](O)[C@H](O)[C@H](O)CO)N1)=O
Appearance
Solid powder
Purity
>95% (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 230.22 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: Wang L, Ren B, Liu Y, Lu Y, Chang F, Yang L. 2-acetyl-4-tetrahydroxybutylimidazole and 4-methylimidazole in caramel colours, vinegar and beverages in China. Food Addit Contam Part B Surveill. 2015;8(3):163-8. doi: 10.1080/19393210.2015.1027286. Epub 2015 May 8. PubMed PMID: 25832559. 2: Elsinghorst PW, di Salvo ML, Parroni A, Contestabile R. Inhibition of human pyridoxal kinase by 2-acetyl-4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)imidazole (THI). J Enzyme Inhib Med Chem. 2015 Apr;30(2):336-40. doi: 10.3109/14756366.2014.915396. Epub 2014 Jun 5. PubMed PMID: 24899377. 3: Wang J, Schnute WC. Simultaneous quantitation of 2-acetyl-4-tetrahydroxybutylimidazole, 2- and 4-methylimidazoles, and 5-hydroxymethylfurfural in beverages by ultrahigh-performance liquid chromatography-tandem mass spectrometry. J Agric Food Chem. 2012 Feb 1;60(4):917-21. doi: 10.1021/jf204476x. Epub 2012 Jan 18. PubMed PMID: 22224586. 4: Ohtoyo M, Tamura M, Machinaga N, Muro F, Hashimoto R. Sphingosine 1-phosphate lyase inhibition by 2-acetyl-4-(tetrahydroxybutyl)imidazole (THI) under conditions of vitamin B6 deficiency. Mol Cell Biochem. 2015 Feb;400(1-2):125-33. doi: 10.1007/s11010-014-2268-z. Epub 2014 Nov 9. PubMed PMID: 25381637. 5: Klejdus B, Moravcová J, Lojková L, Vacek J, Kubán V. Solid-phase extraction of 4(5)-methylimidazole (4MeI) and 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)-imidazole (THI) from foods and beverages with subsequent liquid chromatographic-electrospray mass spectrometric quantification. J Sep Sci. 2006 Feb;29(3):378-84. PubMed PMID: 16544879. 6: Lojková L, Klejdus B, Moravcová J, Kubán V. Supercritical fluid extraction (SFE) of 4(5)-methylimidazole (4-MeI) and 2-acetyl-4(5)-(1,2,3,4)-tetrahydroxybutyl-imidazole (THI) from ground-coffee with high-performance liquid chromatographic-electrospray mass spectrometric quantification (HPLC/ESI-MS). Food Addit Contam. 2006 Oct;23(10):963-73. PubMed PMID: 16982517. 7: Goscinny S, Hanot V, Trabelsi H, Van Loco J. Determination of caramel colorants' by-products in liquid foods by ultra-high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2014;31(10):1652-60. doi: 10.1080/19440049.2014.940609. Epub 2014 Aug 28. PubMed PMID: 25060737. 8: Nguyen-Tran DH, Hait NC, Sperber H, Qi J, Fischer K, Ieronimakis N, Pantoja M, Hays A, Allegood J, Reyes M, Spiegel S, Ruohola-Baker H. Molecular mechanism of sphingosine-1-phosphate action in Duchenne muscular dystrophy. Dis Model Mech. 2014 Jan;7(1):41-54. doi: 10.1242/dmm.013631. Epub 2013 Sep 25. PubMed PMID: 24077965; PubMed Central PMCID: PMC3882047. 9: Bradbury MG, Doherty KV, Parish CR, Lyons AB. The immunosuppressive compound 2-acetyl-4-tetrahydroxybutyl imidazole inhibits the allogeneic mixed lymphocyte reaction by sequestration of a recirculating subpopulation of T cells. Immunology. 1996 Jan;87(1):80-5. PubMed PMID: 8666439; PubMed Central PMCID: PMC1383971. 10: Moretton C, Crétier G, Nigay H, Rocca JL. Heart-cutting two-dimensional liquid chromatography methods for quantification of 2-acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole in Class III caramel colours. J Chromatogr A. 2008 Jul 11;1198-1199:73-9. doi: 10.1016/j.chroma.2008.04.081. Epub 2008 May 14. PubMed PMID: 18538331. 11: Phillips JA, Paine AJ. Effect of pyridoxine on the disposition and lymphopenic effects of 2-acetyl-4(5)-tetrahydroxybutyl imidazole in the rat. Xenobiotica. 1990 Jun;20(6):555-62. PubMed PMID: 2219951. 12: Gobin SJ, Paine AJ. Effect of oral and parenteral administration of B6 vitamers on the lymphopenia produced by feeding ammonia caramel or 2-acetyl-4(5)-(1,2,3,4-tetrahydroxy)butylimidazole to rats. Food Chem Toxicol. 1989 Oct;27(10):627-30. PubMed PMID: 2606399. 13: Reeve VE, Boehm-Wilcox C, Bosnic M, Rozinova E. Suppressive effect of 2-acetyl-4-tetrahydroxybutylimidazole on contact hypersensitivity in the Skh: HR hairless mouse. Int Arch Allergy Immunol. 1993;102(1):101-6. PubMed PMID: 8400881. 14: Gobin SJ, Paine AJ. Effects of 2-acetyl-4-tetrahydroxybutyl imidazole (THI) on the thymus of rats. Thymus. 1992 Aug;20(1):17-30. PubMed PMID: 1519312. 15: Gugasyan R, Clouston D, Mandel T, Wicks I. Prevention of splenic granuloma formation in adjuvant arthritis by 2-acetyl-4-tetrahydroxybutylimidazole (THI). Immunol Lett. 1997 Aug;58(3):133-8. PubMed PMID: 9293393. 16: Kröplien U. Quantitative analysis of 2-acetyl-4(5)-tetrahydroxybutylimidazole. J Chromatogr. 1986 Jul 18;362(2):286-90. PubMed PMID: 3745368. 17: Lawrence JF, Charbonneau CF. Direct method for the determination of 2-acetyl-4(5)-tetrahydroxybutylimidazole in caramel colours and beers by high-performance liquid chromatography with absorbance detection. J Chromatogr. 1987 Oct 16;407:405-7. PubMed PMID: 3429516. 18: Yu XQ, Kramer J, Moran L, O'Neill E, Nouraldeen A, Oravecz T, Wilson AG. Pharmacokinetic/pharmacodynamic modelling of 2-acetyl-4(5)-tetrahydroxybutyl imidazole-induced peripheral lymphocyte sequestration through increasing lymphoid sphingosine 1-phosphate. Xenobiotica. 2010 May;40(5):350-6. doi: 10.3109/00498251003611376. PubMed PMID: 20175664. 19: Houben GF, van den Berg H, Kuijpers MH, Lam BW, van Loveren H, Seinen W, Penninks AH. Effects of the color additive caramel color III and 2-acetyl-4(5)-tetrahydroxybutylimidazole (THI) on the immune system of rats. Toxicol Appl Pharmacol. 1992 Mar;113(1):43-54. PubMed PMID: 1553755. 20: Schwab SR, Pereira JP, Matloubian M, Xu Y, Huang Y, Cyster JG. Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients. Science. 2005 Sep 9;309(5741):1735-9. PubMed PMID: 16151014.