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94944-70-4 Usage


1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE, also known as THI (94944-70-4), is a biologically active impurity found in caramel food coloring. It is a potent inhibitor of sphingosine-1-phosphate (S1P) lyase, which plays a crucial role in the modulation of immune responses. THI disrupts lymphocyte egress from lymphoid tissue by interfering with S1P gradients, exhibiting novel immunomodulatory activity. Its biochemical mechanism may represent a new target for the development of a new generation of immunosuppressants.


Used in Immunosuppressive Applications:
1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE is used as an immunosuppressive agent for the treatment of autoimmune disorders. By inhibiting S1P lyase, it increases lymphoid tissue S1P concentrations, reducing lymphocyte egress from thymus and peripheral lymphoid organs. This results in reversible lymphopenia and therapeutic levels of immunosuppression without causing non-lymphoid lesions associated with synthetic S1P receptor agonists.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-[4-(1,2,3,4-TETRAHYDROXYBUTYL)-1H-IMIDAZOL-2-YL]ETHANONE is used as a potential drug candidate for the development of new immunosuppressants. Its unique mechanism of action and ability to modulate immune responses make it a promising option for treating various autoimmune and inflammatory conditions.

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.


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

Check Digit Verification of cas no

The CAS Registry Mumber 94944-70-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,4,9,4 and 4 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 94944-70:
174 % 10 = 4
So 94944-70-4 is a valid CAS Registry Number.

94944-70-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (H63416)  2-Acetyl-4-(1,2,3,4-tetrahydroxybutyl)imidazole, 97%   

  • 94944-70-4

  • 250mg

  • 12495.0CNY

  • Detail
  • Sigma

  • (T6330)  THI  

  • 94944-70-4

  • T6330-1MG

  • 1,736.28CNY

  • Detail
  • Sigma

  • (T6330)  THI  

  • 94944-70-4

  • T6330-5MG

  • 7,096.05CNY

  • Detail
  • Sigma

  • (T6330)  THI  

  • 94944-70-4

  • T6330-25MG

  • 18,486.00CNY

  • Detail



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017


1.1 GHS Product identifier

Product name 1-[5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl]ethanone

1.2 Other means of identification

Product number -
Other names C9H14N2O5

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:94944-70-4 SDS

94944-70-4Relevant articles and documents

Asymmetric synthesis of (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole


, p. 5969 - 5972 (1995)

A method for preparing the biologically active compound (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole 1 using a palladium (0) catalysed coupling of 1-ethoxymethyl-4-iodomidazole 2 to the functionalised vinylstannane 3 and the Sharpless catalytic asymmetric dihydroxylation is reported.

A Convenient Synthesis of 2-Acetyl-4(5)-(1(R),2(S),3(R),4-tetrahydroxybutyl)imidazole

Halweg, Kim M.,Buechi, George

, p. 1134 - 1136 (1985)


Practical synthesis of potent sphingosine-1-phosphate lyase inhibitors THI and LX2931

Zhang, Haiming,Yan, Jie,Bednarz, Mark S.,Hernandez, Gonzalo,Lu, Yuelie,Courtney, Lawrence F.,Chen, Jason,Hu, Weifeng,Liu, Renmao,Yang, Xiaogen,Wu, Wenxue

, p. 4041 - 4046 (2013/06/26)

A practical and scalable synthesis of in vivo sphingosine-1-phosphate lyase inhibitor LX2931 (1) is described. The synthetic route features an improved Büchi cyclocondensation of 2-ethoxyacrylonitrile (3) with either 1-amino-1-deoxy-d-fructose acetate (4a) or d-(+)-glucosamine hydrochloride (4b) to produce 1-(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)ethanone (2, THI), followed by oximation of THI and acid-promoted oxime isomerization to give LX2931 (1).

Inhibition of sphingosine-1-phosphate lyase for the treatment of autoimmune disorders

Bagdanoff, Jeffrey T.,Donoviel, Michael S.,Nouraldeen, Amr,Tarver, James,Fu, Qinghong,Carlsen, Marianne,Jessop, Theodore C.,Zhang, Haiming,Hazelwood, Jill,Nguyen, Huy,Baugh, Simon D. P.,Gardyan, Michael,Terranova, Kristen M.,Barbosa, Joseph,Yan, Jack,Bednarz, Mark,Layek, Suman,Courtney, Lawrence F.,Taylor, Jerry,Digeorge-Foushee, Ann Marie,Gopinathan, Suma,Bruce, Debra,Smith, Traci,Moran, Liam,O'Neill, Emily,Kramer, Jeff,Lai, Zhong,Kimball, S. David,Liu, Qingyun,Sun, Weimei,Yu, Sean,Swaffield, Jonathan,Wilson, Alan,Main, Alan,Carson, Kenneth G.,Oravecz, Tamas,Augeri, David J.

experimental part, p. 3941 - 3953 (2010/02/17)

During nearly a decade of research dedicated to the study of sphingosine signaling pathways, we identified sphingosine-1-phosphate lyase (S1PL) as a drug target for the treatment of autoimmune disorders. S1PL catalyzes the irreversible decomposition of sphingosine-1-phosphate (S1P) by a retro-aldol fragmentation that yields hexadecanaldehyde and phosphoethanolamine. Genetic models demonstrated that mice expressing reduced S1PL activity had decreased numbers of circulating lymphocytes due to altered lymphocyte trafficking, which prevented disease development in multiple models of autoimmune disease. Mechanistic studies of lymphoid tissue following oral administration of 2-acetyl-4(5)-(1(R),2(S),3(R),4-tetrahydroxybutyl)-imidazole (THI) 3 showed a clear relationship between reduced lyase activity, elevated S1P levels, and lower levels of circulating lymphocytes. Our internal medicinal chemistry efforts discovered potent analogues of 3 bearing heterocycles as chemical equivalents of the pendant carbonyl present in the parent structure. Reduction of S1PL activity by oral administration of these analogues recapitulated the phenotype of mice with genetically reduced S1PL expression.

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