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T6330

Sigma-Aldrich

THI

Synonyme(s) :

2-ATHBI, 2-Acetyl-4-tetrahydroxybutyl Imidazole; 1-[5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl]-ethanone

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About This Item

Formule empirique (notation de Hill):
C9H14N2O5
Numéro CAS:
94944-70-4
Poids moléculaire :
230.22
Numéro MDL:
MFCD08752516
Code UNSPSC :
12352211
ID de substance PubChem :
329826636
Nomenclature NACRES :
NA.77

Forme

powder

Niveau de qualité

100

Couleur

white to light brown

Solubilité

DMSO: 2 mg/mL, clear (warmed)

Température de stockage

2-8°C

Chaîne SMILES 

CC(=O)c1nc(c[nH]1)[C@@H](O)[C@H](O)[C@H](O)CO

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

Clé InChI

CQSIXFHVGKMLGQ-BWZBUEFSSA-N

Actions biochimiques/physiologiques

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.
THI is an inhibitor of sphingosine-1-phosphate lyase and acts as an immunosuppressant. 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.

Notes préparatoires

THI is soluble in DMSO at a concentration that is greater than 5 mg/ml.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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T E Mandel et al.
Clinical and experimental immunology, 88(3), 414-419 (1992-06-01)
The effect of oral administration of THI, a compound present in ammonia caramel food colouring, was studied in spontaneous and induced murine diabetes mellitus. Continuous administration of THI at 400 ppm in drinking water reduced the prevalence of spontaneous diabetes
Shenhe Liu et al.
Frontiers in genetics, 10, 209-209 (2019-03-29)
Heat stress has a detrimental effect on the physiological and production performance of buffaloes. Elucidating the underlying mechanisms of heat stress is challenging, therefore identifying candidate genes is urgent and necessary. We evaluated the response of buffaloes (n = 30)
Yuri M Klyachkin et al.
Stem cells translational medicine, 4(11), 1333-1343 (2015-09-16)
Acute myocardial infarction (AMI) triggers mobilization of bone marrow (BM)-derived stem/progenitor cells (BMSPCs) through poorly understood processes. Recently, we postulated a major role for bioactive lipids such as sphingosine-1 phosphate (S1P) in mobilization of BMSPCs into the peripheral blood (PB).
G F Houben et al.
Toxicology and applied pharmacology, 113(1), 43-54 (1992-03-01)
Administration of ammonia caramel color (AC) to rats may decrease blood lymphocyte counts, specifically in rats fed a diet low in vitamin B6. This effect is associated with 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI). To characterize and compare the effects of AC and THI
G F Houben et al.
Fundamental and applied toxicology : official journal of the Society of Toxicology, 20(1), 30-37 (1993-01-01)
Administration of the color additive caramel color III (AC) may cause a reduction in total white blood cell counts in rats due to reduced lymphocyte counts. Beside lymphopenia, several other effects in rat have been described. The effects are caused
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