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T6330

Sigma-Aldrich

THI

Synonym(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

Empirical Formula (Hill Notation):
C9H14N2O5
CAS Number:
94944-70-4
Molecular Weight:
230.22
MDL number:
MFCD08752516
UNSPSC Code:
12352211
PubChem Substance ID:
329826636
NACRES:
NA.77

form

powder

Quality Level

100

color

white to light brown

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

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

InChI key

CQSIXFHVGKMLGQ-BWZBUEFSSA-N

Biochem/physiol Actions

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.

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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
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).
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)
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
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