2-Acetyl-4(5)-tetrahydroxybutylimidazole

Base Information

• Chemical Name: 2-Acetyl-4(5)-tetrahydroxybutylimidazole
• CAS No.: 94944-70-4
• Molecular Formula: C9H14 N2 O5
• Molecular Weight: 230.221
• Hs Code.: 29332900
• European Community (EC) Number: 687-101-9
• UNII: HW195J55G1
• DSSTox Substance ID: DTXSID20241695
• Nikkaji Number: J828.010J
• Wikidata: Q27088980
• ChEMBL ID: CHEMBL488336
• Mol file: 94944-70-4.mol

Synonyms:2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole;2-acetyl-4(5)-tetrahydroxybutylimidazole;2-acetyl-4-tetrahydroxybutylimidazole;2-ATHBI

Chemical Property of 2-Acetyl-4(5)-tetrahydroxybutylimidazole

Chemical Property:

• Vapor Pressure: 6.58E-16mmHg at 25°C
• Melting Point: approximate 230℃ (dec.)
• Boiling Point: 613.5°Cat760mmHg
• PKA: 10.63±0.10(Predicted)
• Flash Point: 324.8°C
• PSA: 126.67000
• Density: 1.536g/cm³
• LogP: -1.64020
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble2mg/mL, clear (warmed)
• Water Solubility.: Soluble in distilled water, DMSO (>5 mg/ml), clear (warmed), and PBS pH 7.2 (~0.15 mg/ml).
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 230.09027155
• Heavy Atom Count: 16
• Complexity: 250

Purity/Quality:

99.0%Min ^*data from raw suppliers

(R,S,R)-2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)-imidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=NC=C(N1)C(C(C(CO)O)O)O
• Isomeric SMILES: CC(=O)C1=NC=C(N1)[C@H]([C@@H]([C@@H](CO)O)O)O
• 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. 2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole used for treatment of autoimmune disorders.

Technology Process of 2-Acetyl-4(5)-tetrahydroxybutylimidazole

There total 16 articles about 2-Acetyl-4(5)-tetrahydroxybutylimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

2-ethoxyacrylonitrile (19479-65-3) + 1-amino-1-deoxy-D-arabino-hexulose acetate (6333-49-9,54990-71-5) → (1'R,2'S,3'R)-2-acetyl-4(5)-(1',2',3',4'-tetrahydroxy-1'-butyl)imidazole (94944-70-4)

Guidance literature:

2-ethoxyacrylonitrile; With sodium methylate; In methanol; at 20 ℃; for 3.25h;

1-amino-1-deoxy-D-arabino-hexulose acetate; In methanol; at 20 ℃; for 6.25h;

With methanol; water; sodium methylate; acetic acid; more than 3 stages;

Reference yield: 82.0%

2-ethoxyacrylonitrile (19479-65-3) + 1-amino-1-deoxy-D-fructose acetic acid salt (1201794-87-7) → (1'R,2'S,3'R)-2-acetyl-4(5)-(1',2',3',4'-tetrahydroxy-1'-butyl)imidazole (94944-70-4)

Guidance literature:

2-ethoxyacrylonitrile; With sodium methylate; In methanol; at 20 ℃; for 1h;

1-amino-1-deoxy-D-fructose acetic acid salt; In methanol; at 20 ℃; for 6h; Further stages;

DOI:10.1021/jm900278w

Reference yield: 74.0%

2-ethoxyacrylonitrile (19479-65-3) + (+)-D-glucosamine hydrochloride (1078691-95-8) → (1'R,2'S,3'R)-2-acetyl-4(5)-(1',2',3',4'-tetrahydroxy-1'-butyl)imidazole (94944-70-4)

Guidance literature:

2-ethoxyacrylonitrile; (+)-D-glucosamine hydrochloride; With sodium methylate; sodium acetate; In methanol; at 10 - 25 ℃;

With sodium methylate; In methanol; at 10 - 25 ℃;

With acetic acid; In methanol; water; at 50 ℃; for 3h;

upstream raw materials:

methanol

2-ethoxyacrylonitrile

D-(+)-glucosamine hydrochloride

1-amino-1-deoxy-D-fructose acetic acid salt

Downstream raw materials:

(E)-ethyl 2-(1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)ethylidene)hydrazinecarboxylate

(1R,2S,3R)-1-(2-(1-hydroxyethyl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol

1-(1-methyl-4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone

Refernces

• 1、 Cliff, Matthew D.,Pyne, Stephen G.. "Asymmetric synthesis of 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles". . p. 1023 - 1032. Retrieved 1997.
• 2、 -. "COMPOUNDS AND USE THEREOF FOR THE TREATMENT OF INFECTIOUS DISEASES AND CANCER". Page/Page column 35-36; 41-42. . Retrieved 2021/02/26.
• 3、 -. "METHODS OF PREPARING 1-(4-((1R,2S,3R)-1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL)ETHANONE". Page/Page column 2. . Retrieved 2011/05/05.