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T6330

Sigma-Aldrich

THI

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C9H14N2O5
Numero CAS:
94944-70-4
Peso molecolare:
230.22
Numero MDL:
MFCD08752516
Codice UNSPSC:
12352211
ID PubChem:
329826636
NACRES:
NA.77

Stato

powder

Livello qualitativo

100

Colore

white to light brown

Solubilità

DMSO: 2 mg/mL, clear (warmed)

Temperatura di conservazione

2-8°C

Stringa SMILE

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
CQSIXFHVGKMLGQ-BWZBUEFSSA-N

Azioni biochim/fisiol

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.

Nota sulla preparazione

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
047M4622V
084M4625V
032M4626V
011M4614V

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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
Jaap P P Saers et al.
Journal of human evolution, 135, 102654-102654 (2019-08-30)
The human foot is highly derived relative to that of other hominoids and therefore a topic of intense research in paleoanthropology. While trabecular bone is thought to be highly plastic in response to habitual behavior, knowledge of how trabecular structure
K V Nordlund et al.
Journal of dairy science, 102(7), 6495-6507 (2019-04-30)
Heat load is a challenge for high-producing dairy cows, with adverse consequences on production, reproduction, and welfare. The objectives of this observational study in 2 commercial dairy herds were to determine the effects of environmental heat stress on standing and
V E Reeve et al.
International archives of allergy and immunology, 102(1), 101-106 (1993-01-01)
The compound 2-acetyl-4-tetrahydroxybutylimidazole (THI), a component of ammonia caramel, has been shown to cause lymphopenia and to impair several immune functions in rats and mice. In this study we show that THI effectively suppresses contact hypersensitivity dose responsively in the
S J Gobin et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 27(10), 627-630 (1989-10-01)
The ability of B6 vitamers to prevent the lymphopenic effects of ammonia caramel fed to rats has been evaluated. Diets containing 10 ppm pyridoxine or pyridoxal prevented the lymphopenia produced in rats consuming an 8% (w/v) solution of ammonia caramel
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