1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE

CAS NO.：94944-70-4
Empirical Formula: C9H14N2O5
Molecular Weight: 230.22
MDL number: MFCD03844698
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-06 19:41:26

What is 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE?

Description

THI (94944-70-4) was identified as a biologically active impurity in caramel food coloring.1 It is a potent inhibitor of sphingosine-1-phosphate (S1P) lyase.2 It disrupts lymphocyte egress from lymphoid tissue by interfering with S1P gradients.3,4 The novel immunomodulatory activity of THI and its biochemical mechanism may represent a new target for the development of new generation of immunosuppressants.5

The Uses of 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE

Sphingosine-1-phosphate (S1P) lyase catalyzes the irreversible decomposition of S1P to hexadecanaldehyde and phosphoethanolamine. 2-Acetyl-5-tetrahydroxybutyl imidazole (THI) is an inhibitor of S1P lyase. Because S1P lyase is primarily expressed in lymphatic tissue, treatment of mice with THI (50 μg/ml in drinking water) increases lymphoid tissue S1P concentrations 100-fold, reducing lymphocyte egress from thymus and peripheral lymphoid organs. The resulting lymphopenia is reversible following cessation of THI treatment. Reducing S1P lyase activity results in therapeutic levels of immunosuppression without the non-lymphoid lesions that result from synthetic S1P receptor agonists.

The Uses of 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE

2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole used for treatment of autoimmune disorders.

What are the applications of Application

2-Acetyl-4-tetrahydroxybutylimidazole is an SP-lyase inhibitor

Biochem/physiol Actions

2-Acetyl-5-tetrahydroxybutyl imidazole (THI) can block S1P lyase in vivo and up-regulates circulatory and tissue S1P levels. It has the ability to repress dystrophic muscle degeneration.

References

1) MacKenzie et al. (1992), Toxicity Studies of Caramel Colour III and 2-Acetyl-4(5)-Tetrahydroxybutylimidazole in F344 rats; Food Chem. Toxicol. 30 417 2) Ohtoyo et al. (2015), Sphingosine 1-phosphate lyase inhibition by 2-acetyl-4-(tetrahydroxybutyl)imidazole (THI) under conditions of vitamin B6 deficiency; Mol.Cell Biochem. 400 125 3) Gugasyan et al. (1998), Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole; Immunology 93 398 4) Schwab et al. (2005), Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients; Science 309 1735 5) Bradbury et al. (1997), The immunomodulatory compound 2-acetyl-4-tetrahydroxybutyl imidazole causes sequestration of lymphocytes in non-lymphoid tissue; Immunol. Cell Biol. 75 497

Properties of 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE

Melting point:	approximate 230℃ (dec.)
Boiling point:	613.5±65.0 °C(Predicted)
Density	1.536±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: soluble2mg/mL, clear (warmed)
pka	10.63±0.10(Predicted)
form	Powder
color	white to light brown
Water Solubility	Soluble in distilled water, DMSO (>5 mg/ml), clear (warmed), and PBS pH 7.2 (~0.15 mg/ml).
Stability:	Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.
CAS DataBase Reference	94944-70-4

Safety information for 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P330:Rinse mouth.