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

MedKoo CAT#: 581009

CAS#: 94944-70-4

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


Price and Availability

Size
Price

5mg
USD 560
Size
Price

10mg
USD 960
Size
Price

2-ATHBI (THI), purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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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


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


Technical Data

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).

Harmonized System Code:
293490


References

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.