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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

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. 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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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