A metabolite of histidine
Related Products
Isomer(s)
29972A6770
Parent Compound(s)
33904Histidine
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Imidazole Propionate

Item No. 33458

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1H-imidazole-5-propanoic acid
CAS Number
1074-59-5
Synonyms
  • Deamino-histidine
  • Imidazolepropionic Acid
  • NSC 66737
Molecular Formula
C6H8N2O2
Formula Weight
140.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 5 mg/ml
SMILES
O=C(CCC1=CN=CN1)O
InChi Code
InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)
InChi Key
ZCKYOWGFRHAZIQ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $46

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    100 mg

    $81

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    250 mg

    $157

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    1 g

    $355

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Imidazole propionate is a metabolite of histidine.1 It is formed from histidine via a urocanate intermediate in gut microbiota by urocanate reductase (urdA). Imidazole propionate (100 µM) decreases protein levels of insulin receptor substrate 1 (IRS-1), IRS-2, and phosphorylated Akt and increases levels of the mTORC1 activation marker phosphorylated p70 ribosomal S6 kinase (p70S6K) in primary mouse hepatocytes. It induces deficits in glucose tolerance in germ-free and conventionally raised mice when administered at doses of 500 and 100 µg/animal, respectively. It also prevents reductions in blood glucose levels induced by metformin (Item No. 13118) in mice.2 Plasma levels of imidazole propionate are increased in patients with type 2 diabetes.1,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Koh, A., Molinaro, A., Ståhlman, M., et al. Microbially produced imidazole propionate impairs insulin signaling through mTORC1. Cell 175(4), 947-961 (2018).

    2. Koh, A., Mannerås-Holm, L., Yunn, N.-O., et al. Microbial imidazole propionate affects responses to metformin through p38γ-dependent inhibitory AMPK phosphorylation. Cell Metab. 32(4), 643-653 (2020).