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Merck
CN

T6330

THI

sphingosine-1-phosphate lyase inhibitor, powder

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
UNSPSC Code:
12352211
PubChem Substance ID:
329826636
NACRES:
NA.77
MDL number:
MFCD08752516
Form:
powder
Quality level:
100

Key Documents

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Product Name

THI,

SMILES string

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

InChI key

CQSIXFHVGKMLGQ-BWZBUEFSSA-N

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

form

powder

color

white to light brown

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

Quality Level

100

Related Categories

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.
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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000523096
0000523096
0000255823
0000255823
0000130647

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M G Bradbury et al.
Immunology, 87(1), 80-85 (1996-01-01)
2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI) is an immunosuppressive component of caramel food colouring that causes lymphopenia in mice and rats by an unknown mechanism. In this study we investigated some of the affects of THI on the murine immune system. Initially we showed
M G Bradbury et al.
Immunology and cell biology, 75(5), 497-502 (1998-01-16)
2-Acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl) imidazole (THI) is an immunomodulatory compound which causes a reversible lymphopenia in mice by an unknown mechanism. In this study, we investigated the whereabouts of cells lost from the blood and the spleen during THI treatment Homing studies following
V E Reeve et al.
The American journal of clinical nutrition, 61(3), 571-576 (1995-03-01)
Evidence exists implicating the epidermal ultraviolet B (UVB) photoproduct cis-urocanic acid as an immunogenic mediator of the systemic suppression of T cell-mediated immunity by UVB exposure. Cis-urocanic acid appears to act via histamine receptor pathways, and histamine receptor antagonists and
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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