1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE
![1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE Structure](CAS/GIF/94944-70-4.gif)
- CAS No.
- 94944-70-4
- Chemical Name:
- 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE
- Synonyms
- 2-Athbi;Inhibitor,inhibit,2 ATHBI,2ATHBI;2-Acetyl-5-tetrahydroxybutyl Imidazole;2-acetyl-4(5)-tetrahydroxybutylimidazole;2-Acetyl-5-tetrahydroxybutyl iMidazole (THI);2-Acetyl-4-tetrahydroxybutylimidazole Standard;2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)iMidazole, 97%;2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole, 97%,;(R,S,R)-2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)-imidazole;2-ACETYL-4(5)-(1,2,3,4-TETRAHYDROXYBUTYL)-IMIDAZOLE (THI)
- CBNumber:
- CB0371535
- Molecular Formula:
- C9H14N2O5
- Molecular Weight:
- 230.22
- MDL Number:
- MFCD03844698
- MOL File:
- 94944-70-4.mol
| 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. |
| CAS DataBase Reference | 94944-70-4 |
| FDA UNII | HW195J55G1 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302 | |||||||||
| Precautionary statements | P264-P270-P301+P312a-P330-P501a | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 22 | |||||||||
| WGK Germany | 3 | |||||||||
| HS Code | 29332900 | |||||||||
| NFPA 704 |
|
1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE price More Price(21)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | T6330 | THI | 94944-70-4 | 1mg | $210 | 2024-03-01 | Buy |
| Sigma-Aldrich | T6330 | THI | 94944-70-4 | 5mg | $853 | 2024-03-01 | Buy |
| Alfa Aesar | H63416 | 2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole, 97% | 94944-70-4 | 250mg | $2382 | 2024-03-01 | Buy |
| Cayman Chemical | 13222 | 2-Acetyl-5-tetrahydroxybutyl Imidazole ≥95% | 94944-70-4 | 500μg | $64 | 2024-03-01 | Buy |
| Cayman Chemical | 13222 | 2-Acetyl-5-tetrahydroxybutyl Imidazole ≥95% | 94944-70-4 | 1mg | $119 | 2024-03-01 | Buy |
1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE Chemical Properties,Uses,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
2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole used for treatment of autoimmune disorders.
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.
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) MacKenzie et al. (1992), Toxicity Studies of Caramel Colour III and 2-Acetyl-4(5)-Tetrahydroxybutylimidazole in F344 rats; Food Chem. Toxicol. 30 417 2) Ohtoyo et al. (2015), Sphingosine 1-phosphate lyase inhibition by 2-acetyl-4-(tetrahydroxybutyl)imidazole (THI) under conditions of vitamin B6 deficiency; Mol.Cell Biochem. 400 125 3) Gugasyan et al. (1998), Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole; Immunology 93 398 4) Schwab et al. (2005), Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients; Science 309 1735 5) Bradbury et al. (1997), The immunomodulatory compound 2-acetyl-4-tetrahydroxybutyl imidazole causes sequestration of lymphocytes in non-lymphoid tissue; Immunol. Cell Biol. 75 497
1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE Preparation Products And Raw materials
1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| Shanghai Acmec Biochemical Technology Co., Ltd. | +undefined18621343501 | product@acmec-e.com | China | 33349 | 58 |
| J & K SCIENTIFIC LTD. | 010-82848833 400-666-7788 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Alfa Aesar | 400-6106006 | saleschina@alfa-asia.com | China | 30132 | 84 |
| Hangzhou Sage Chemical Co., Ltd. | +86057186818502 13588463833 | info@sagechem.com | China | 10269 | 58 |
| Nanjing JinruiJiuAn Biotechnology Co., Ltd. | 025-58196018 800028039 | sales@fartop.net | China | 2231 | 55 |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4428 | 55 |
| ChemStrong Scientific Co.,Ltd | 0755-66853366 13670046396 | sales@chem-strong.com | China | 17982 | 56 |
| Shanghai Kewel Chemical Co., Ltd. | 021-64609169 18901607656 | greensnown@163.com | China | 9911 | 50 |