ChemicalBook > CAS DataBase List > 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE

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

Product Name
1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE
CAS No.
94944-70-4
Chemical Name
1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE
Synonyms
2-Athbi;Inhibitor,inhibit,2 ATHBI,2ATHBI;2-Acetyl-5-tetrahydroxybutyl Imidazole;2-acetyl-4(5)-tetrahydroxybutylimidazole;2-Acetyl-5-tetrahydroxybutyl iMidazole (THI);2-Acetyl-4-tetrahydroxybutylimidazole Standard;2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)iMidazole, 97%;2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole, 97%,;(R,S,R)-2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)-imidazole;2-ACETYL-4(5)-(1,2,3,4-TETRAHYDROXYBUTYL)-IMIDAZOLE (THI)
CBNumber
CB0371535
Molecular Formula
C9H14N2O5
Formula Weight
230.22
MOL File
94944-70-4.mol
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1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE Property

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
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
HS Code 
29332900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P330Rinse mouth.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T6330
Product name
THI
Packaging
1mg
Price
$210
Updated
2024/03/01
Sigma-Aldrich
Product number
T6330
Product name
THI
Packaging
5mg
Price
$853
Updated
2024/03/01
Alfa Aesar
Product number
H63416
Product name
2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole, 97%
Packaging
250mg
Price
$2382
Updated
2024/03/01
Cayman Chemical
Product number
13222
Product name
2-Acetyl-5-tetrahydroxybutyl Imidazole
Purity
≥95%
Packaging
500μg
Price
$64
Updated
2024/03/01
Cayman Chemical
Product number
13222
Product name
2-Acetyl-5-tetrahydroxybutyl Imidazole
Purity
≥95%
Packaging
1mg
Price
$119
Updated
2024/03/01
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1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE Chemical Properties,Usage,Production

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

Preparation Products

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94944-70-4, 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONERelated Search:

Zafirlukast URB597 (E)-3-[[[3-[2-(7-CHLORO-2-QUINOLINYL)ETHENYL]PHENYL]-[[(3-DIMETHYLAMINO)-3-OXOPROPYL]THIO]METHYL]THIO]-PROPANOIC ACID, SODIUM SALT JZL 184 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE 1-(4-METHYL-1H-IMIDAZOL-2-YL)-ETHANONE 4-ARABOTETRAHYDROXYBUTYLIMIDAZOLE

  • 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]-
  • Ethanone, 1-[4-(1,2,3,4-tetrahydroxybutyl)-1H-iMidazol-2-yl]-, [1R-(1R*,2S*,3R*)]- (9CI)
  • 2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)iMidazole, 97%
  • 2-Acetyl-5-tetrahydroxybutyl iMidazole (THI)
  • 1-[5-[(1R,2S,3R)-1,2,3,4-Tetrahydroxybutyl]-1H-imidazol-2-yl]ethanone
  • (R,S,R)-2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)-imidazole
  • 2-Acetyl-4-tetrahydroxybutylimidazole Standard
  • 1-(5-(1,1,2,2-Tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone
  • 2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole, 97%,
  • Inhibitor,inhibit,2 ATHBI,2ATHBI
  • 94944-70-4