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

CAS No.：94944-70-4

Important Notice

This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
This product is intended solely for non-clinical research, process development, quality studies, further chemical processing, or chemical synthesis. It must not be used in drug-product manufacturing, clinical trials, clinical diagnosis, or administration to humans or animals, or be sold, used as an input, submitted for regulatory filing, or released as an API or pharmaceutical material.
The purchaser must not use this product, or supply it to another party, for personal consumption, sports or fitness, weight loss, health supplements, food, or animal feed.

View the full Disclaimer

Other grades of this product :

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

Product Name:	1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE
Synonyms:	1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE;2-acetyl-4(5)-tetrahydroxybutylimidazole;2-ACETYL-4(5)-(1,2,3,4-TETRAHYDROXYBUTYL)-IMIDAZOLE (THI);2-Athbi;(1'R,2'S,3'R)-2-acetyl-4(5)-(1',2',3',4'-tetrahydroxy-1'-butyl)imidazole;Ethanone, 1-(4-(1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)-, (1R-(1R,2S,3R*))-;2-Acetyl-5-tetrahydroxybutyl Imidazole;Ethanone, 1-[5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-iMidazol-2-yl]-
CAS:	94944-70-4
MF:	C9H14N2O5
MW:	230.22
EINECS:
Product Categories:
Mol File:	94944-70-4.mol

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

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

Hazard Codes	Xn
Risk Statements	22
WGK Germany	3
HS Code	29332900

MSDS Information

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

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

1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE Preparation Products And Raw materials

Raw materials

(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochloride-->NA-->1,3-Dithiolane-2-carboxaldehyde, 2-methyl--->Intermediate-->1-Amino-1-deoxy-D-fructose Acetate-->alpha-Ethoxyacrylonitrile-->D-Glucosamine hydrochloride-->Methanol

Welcome！

Please leave a message for us or use the following ways to contact us, we will reply to you as soon as possible, and provide you with the most sincere service, thank you.

NO. 18 ,Wujiang Road, Wulidian Street, Jiangbei District, Chongqing
+86-23-6139-8061 +86-13650506873
danny@chemdad.com sales@chemdad.com
www.chemdad.com
WhatsApp +86-13650506873