ChemicalBook CAS DataBase List 1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone

1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone

Product Name1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone
CAS94944-70-4
CBNumberCB0371535
MFC9H14N2O5
MW230.22
MDL NumberMFCD03844698
MOL File94944-70-4.mol
MSDS FileSDS

Chemical Properties

Melting point	approximate 230℃ (dec.)
Boiling point	613.5±65.0 °C(Predicted)
Density	1.536±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: soluble2mg/mL, clear (warmed)
form	Powder
pka	10.63±0.10(Predicted)
color	white to light brown
Water Solubility	Soluble in distilled water, DMSO (>5 mg/ml), clear (warmed), and PBS pH 7.2 (~0.15 mg/ml).
Stability	Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.
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
InChIKey	CQSIXFHVGKMLGQ-BWZBUEFSSA-N
SMILES	CC(=O)c1nc(c[nH]1)[C@@H](O)[C@H](O)[C@H](O)CO
CAS DataBase Reference	94944-70-4
FDA UNII	HW195J55G1
UNSPSC Code	12352211
NACRES	NA.77

Safety

Symbol(GHS)

Signal word

Warning

Hazard statements

H302

Precautionary statements

P264-P270-P301+P312a-P330-P501a

Hazard Codes

Risk Statements

WGK Germany

HS Code

29332900

Storage Class

11 - Combustible Solids

NFPA 704:

	1
2		0

1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone Price

Product number	Packaging	Price	Product description	Buy
Sigma-Aldrich T6330	1mg	$232	THI	Buy
Sigma-Aldrich T6330	5mg	$941	THI	Buy
Cayman Chemical 13222	500μg	$71	2-Acetyl-5-tetrahydroxybutyl Imidazole ≥95%	Buy
Cayman Chemical 13222	1mg	$131	2-Acetyl-5-tetrahydroxybutyl Imidazole ≥95%	Buy
Cayman Chemical 13222	5mg	$547	2-Acetyl-5-tetrahydroxybutyl Imidazole ≥95%	Buy

1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone Chemical Properties,Usage,Production

Description

THI (94944-70-4) was identified as a biologically active impurity in caramel food coloring.1 It is a potent inhibitor of sphingosine-1-phosphate (S1P) lyase.2 It disrupts lymphocyte egress from lymphoid tissue by interfering with S1P gradients.3,4 The novel immunomodulatory activity of THI and its biochemical mechanism may represent a new target for the development of new generation of immunosuppressants.5

Uses

Sphingosine-1-phosphate (S1P) lyase catalyzes the irreversible decomposition of S1P to hexadecanaldehyde and phosphoethanolamine. 2-Acetyl-5-tetrahydroxybutyl imidazole (THI) is an inhibitor of S1P lyase. Because S1P lyase is primarily expressed in lymphatic tissue, treatment of mice with THI (50 μg/ml in drinking water) increases lymphoid tissue S1P concentrations 100-fold, reducing lymphocyte egress from thymus and peripheral lymphoid organs. The resulting lymphopenia is reversible following cessation of THI treatment. Reducing S1P lyase activity results in therapeutic levels of immunosuppression without the non-lymphoid lesions that result from synthetic S1P receptor agonists.

Uses

2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole used for treatment of autoimmune disorders.

Biochem/physiol Actions

2-Acetyl-5-tetrahydroxybutyl imidazole (THI) can block S1P lyase in vivo and up-regulates circulatory and tissue S1P levels. It has the ability to repress dystrophic muscle degeneration.

References

[1] K.M. MACKENZIE . Toxicity studies of Caramel Colour III and 2-acetyl-4(5)-tetrahydroxybutylimidazole in F344 rats[J]. Food and Chemical Toxicology, 1992, 30 5: Pages 417-425. DOI:10.1016/0278-6915(92)90069-w
[2] MAMORU OHTOYO. Sphingosine 1-phosphate lyase inhibition by 2-acetyl-4-(tetrahydroxybutyl)imidazole (THI) under conditions of vitamin B6 deficiency.[J]. Molecular and Cellular Biochemistry, 2015, 400 1-2: 125-133. DOI:10.1007/s11010-014-2268-z
[3] GUGASYAN‡. Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole[J]. Immunology, 2001, 93 3: 398-404. DOI:10.1046/j.1365-2567.1998.00434.x
[4] SUSAN R. SCHWAB. Lymphocyte Sequestration Through S1P Lyase Inhibition and Disruption of S1P Gradients[J]. Science, 2005, 309 5741. DOI:10.1126/science.1113640
[5] MG BRADBURY CR P MR Qiu. The immunomodulatory compound 2-acetyl-4-tetrahydroxybutyl imidazole causes sequestration of lymphocytes in non-lymphoid tissues[J]. Immunology & Cell Biology, 1997, 75 5: 497-502. DOI:10.1038/icb.1997.77

1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone synthesis

Preparation Products And Raw materials

1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
J & K SCIENTIFIC LTD.	18210857532 18210857532	jkinfo@jkchemical.com	China	96815	76
Alfa Aesar	400-6106006	saleschina@alfa-asia.com	China	30103	84
Hangzhou Sage Chemical Co., Ltd.	+86057186818502 13588463833	info@sagechem.com	China	10265	58
Nanjing JinruiJiuAn Biotechnology Co., Ltd.	025-58196018 800028039	sales@fartop.net	China	2227	55
Guangzhou Isun Pharmaceutical Co., Ltd	020-39119399 18927568969	isunpharm@qq.com	China	4773	55
Quality Control Solutions Ltd.	0755-66853366 13670046396	orders@qcsrm.com	China	18188	56
Shanghai Kewel Chemical Co., Ltd.	021-64609169 18901607656	greensnown@163.com	China	9883	50
Chizhou Kailong Import and Export Trade Co., Ltd.		xg01_gj@163.com	China	9413	50
Sigma-Aldrich	021-61415566 800-8193336	orderCN@merckgroup.com	China	51389	80
Lanzhou Angeli Biochemical Technology Co., Ltd.	0931-8235634 13321316780	1455540579@qq.com	China	957	55

View Latest Prices from 1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone manufacturers

1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanone Spectrum

94944-70-4, 1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]ethanoneRelated Search

Send Inquiry