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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 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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Siyu Chen et al.
Scientific reports, 8(1), 14606-14606 (2018-10-04)
The microbiome has emerged as a new player on behavior, physiology and stress because of its significant effects on the brain-gut axis. The aim of this study was to increase our understanding of brain-gut function in dairy cows. We investigated
S J Gobin et al.
International journal of immunopharmacology, 14(4), 687-697 (1992-05-01)
2-Acetyl-4-tetrahydroxybutyl imidazole (THI), a component of the food colouring ammonia caramel, has been shown to produce a profound and rapid lymphopenia in peripheral blood in the rat. In order to investigate whether the cause of the lymphopenia was due to
Christopher J Thorpe et al.
PloS one, 13(3), e0194810-e0194810 (2018-03-27)
The importance of patch quality for amphibians is frequently overlooked in distribution models. Here we demonstrate that it is highly important for the persistence of endemic and endangered amphibians found in the threatened and fragile ecosystems that are the rocky
C de Heer et al.
Toxicology, 100(1-3), 203-211 (1995-06-26)
SCID mice engrafted with human fetal thymus and liver tissue fragments (SCID-hu mice) are currently considered as a new tool in human immunotoxicological risk assessment. Testing of various immunotoxicants exerting thymotoxicity via different intrathymic target cell types is necessary for
Jaap P P Saers et al.
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