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463494 (R,S,R)-2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)-imidazole

Specifications
References
Purity
≥96%
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
1-[5-[(1R,2S,3R)-1,2,3,4-Tetrahydroxybutyl]-1H-imidazol-2-yl]-ethanone; [1R-(1R*,2S*,3R*)]-1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]-ethanone; 2-ATHBI

(R,S,R)-2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)-imidazole (THI) inhibits sphinogosine-1-phosphate (S1P) lyase for treatment of autoimmune disorders. Sphingosine-1-phosphate (S1P) lyase catalyzes the irreversible decomposition of S1P to hexadecanaldehyde and phosphoethanolamine. Reducing S1P lyase activity results in therapeutic levels of immunosuppression without the non-lymphoid lesions that result from synthetic S1P receptor agonists. 2-Acetyl-4-tetrahydroxybutyl imidazole (THI) is known to induce peripheral blood lymphopenia in rats. Studies in rats have also reported that THI can affect lymphocyte migration and degradation.

Synonyms
1-[5-[(1R,2S,3R)-1,2,3,4-Tetrahydroxybutyl]-1H-imidazol-2-yl]-ethanone; [1R-(1R*,2S*,3R*)]-1-[4-(1,2,3,4-Tetrahydroxybutyl)-1H-imidazol-2-yl]-ethanone; 2-ATHBI
CAS No
94944-70-4
Molecular Formula
C₉H₁₄N₂O₅
Molecular Weight
230.22
Appearance
Off-white to light brown solid
Purity
≥96%
Melting Point
>200ºC (dec.)
Solubility
Aqueous Acid (Slightly, Heated), DMSO (Slightly, Heated)
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
References
Zhang, H., et al.: Tetrahedron, 69, 4041 (2013); Bagdanoff, J.T., et al.: J. Med. Chem., 53, 8650 (2010); Bagdanoff, J.T., et al.: J. Med. Chem., 52, 3941 (2009)
USBio References
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