An inhibitor of S1P lyase in vivo
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

2-Acetyl-5-tetrahydroxybutyl Imidazole

Item No. 13222

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl]-ethanone
CAS Number
94944-70-4
Synonyms
  • 2-Acetyl-4-tetrahydroxybutyl Imidazole
  • 2-ATHBI
  • THI
Molecular Formula
C9H14N2O5
Formula Weight
230.2
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 2 mg/mlPBS (pH 7.2): 0.15 mg/ml
λmax
288 nm
SMILES
CC(=O)c1ncc([C@@H](O)[C@H](O)C(O)CO)[nH]1
InChi Code
InChI=1S/C9H14N2O5/c1-4(13)9-10-2-5(11-9)7(15)8(16)6(14)3-12/h2,6-8,12,14-16H,3H2,1H3,(H,10,11)/t6-,7-,8-/m1/s1
InChi Key
CQSIXFHVGKMLGQ-BWZBUEFSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    500 µg

    $71

    Add

    1 mg

    $131

    Add

    5 mg

    $547

    Add

    10 mg

    $954

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    2-Acetyl-5-tetrahydroxybutyl imidazole (THI) is an inhibitor of sphingosine-1-phosphate (S1P) lyase in vivo.1 THI is not active at S1P lyase in cell-free or cell-based assays but is converted to A6770 in vivo, which is subsequently activated by phosphorylation.2 In mice, THI (50 µg/ml in drinking water) increases S1P levels by 100-fold in lymphoid tissue and reduces lymphocyte egress from thymus and peripheral lymphoid organs.1,3 The resulting lymphopenia is reversible following cessation of THI treatment.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schwab, S.R., Pereira, J.P., Matloubian, M., et al. Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients. Science 309(5741), 1735-1739 (2005).

    2. Ohtoyo, M., Machinaga, N., Inoue, R., et al. Compoent of caramel food coloring, THI, causes lymphopenia indirectly via a key metabolic intermediate. Cell Chem. Biol. 23(5), 555-560 (2016).

    3. Gugasyan, R., Coward, A., O'Connor, L., et al. Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole. Immunology 93(3), 398-404 (1998).

    4. Bradbury, M.G., Doherty, K.V., Parish, C.R., et al. The immunosuppressive compound 2-acetyl-4-tetrahydroxybutyl imidazole inhibits the allogeneic mixed lymphocyte reaction by sequestration of a recirculating subpopulation of T cells. Immunology 87(1), 80-85 (1996).