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About This Item
Empirical Formula (Hill Notation):
C9H14N2O5
CAS Number:
Molecular Weight:
230.22
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
THI, 2-acetyl-5-tetrahydroxybutyl imidazole, powder
assay
>98% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (857393P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 857393P
lipid type
sphingolipids
bioactive lipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
[nH]1c(ncc1[C@@H](O)[C@H](O)[C@H](O)CO)C(=O)C
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
InChI key
CQSIXFHVGKMLGQ-BWZBUEFSSA-N
General description
2-Acetyl-5-tetrahydroxybutyl imidazole (THI) is an inhibitor of sphingosine-1-phosphate lyase (S1P lyase).
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.
Packaging
5 mL Amber Glass Screw Cap Vial (857393P-1mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Molecular mechanism of sphingosine-1-phosphate action in Duchenne muscular dystrophy
Nguyen TDH, et al.
Disease models & mechanisms, 7(1), 41-54 (2014)
Incomplete inhibition of sphingosine 1-phosphate lyase modulates immune system function yet prevents early lethality and non-lymphoid lesions.
Vogel P, et al.
PLoS ONE, 4(1) (2009)
The immunosuppressive compound 2-acetyl-4-tetrahydroxybutyl imidazole inhibits the allogeneic mixed lymphocyte reaction by sequestration of a recirculating subpopulation of T cells.
Bradbury MG, et al.
Immunology, 87, 80-85 (1996)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 857393P-1MG | 04061835191406 |