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T6330

THI

Name: THI
Brand: SIGMA

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

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Sigma-Aldrich

T9033

Thapsigargine

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

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Effects of the color additive caramel color III and 2-acetyl-4(5)-tetrahydroxybutylimidazole (THI) on the immune system of rats.

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

Trabecular bone structure scales allometrically in the foot of four human groups.

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

Thermodynamics of standing and lying behavior in lactating dairy cows in freestall and parlor holding pens during conditions of heat stress.

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

Suppressive effect of 2-acetyl-4-tetrahydroxybutylimidazole on contact hypersensitivity in the Skh: HR hairless mouse.

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

Effect of oral and parenteral administration of B6 vitamers on the lymphopenia produced by feeding ammonia caramel or 2-acetyl-4(5)-(1,2,3,4-tetrahydroxy)butylimidazole to rats.

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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