An active tryptophan metabolite and synthetic intermediate
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Isomer(s)
100070864-formyl Indole
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Indole-3-carboxaldehyde

Item No. 31328

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1H-indole-3-carboxaldehyde
CAS Number
487-89-8
Synonyms
  • Indole-3-formaldehyde
  • β-Indolylaldehyde
  • NSC 10118
Molecular Formula
C9H7NO
Formula Weight
145.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.50 mg/ml
λmax
243, 260, 297 nm
SMILES
O=CC1=CNC2=CC=CC=C21
InChi Code
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChi Key
OLNJUISKUQQNIM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

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    Cayman Chemical
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    Product Description

    Indole-3-carboxyaldehyde is an active metabolite of tryptophan and a synthetic intermediate.1,2,3 It is produced by lactobacilli in the gut microbiota via the indole pyruvate pathway, which is catalyzed by aromatic amino acid aminotransferase (ArAT).1 Indole-3-carboxyaldehyde (18 mg/kg) increases colonic production of IL-22 and restores colonization resistance to C. albicans infection in a wild-type, but not aryl hydrocarbon receptor knockout (Ahr-/-), mouse model of mucosal candidiasis. It also reduces intestinal mucosal damage in a mouse model of colitis induced by dextran sulfate (DSS; Item No. 23250). Indole-3-carboxaldehyde has been used as a synthetic intermediate in the synthesis of Schiff bases and ergot alkaloids.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zelante, T., Iannitti, R.G., Cunha, C., et al. Tryptophan catabolites from microbiota engage aryl hydrocarbon receptor and balance mucosal reactivity via interleukin-22. Immunity 39(2), 372-385 (2013).

    2. Sinha, D., Tiwari, A.K., Singh, S., et al. Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde. Eur. J. Med. Chem. 43(1), 160-165 (2008).

    3. Somei, M. Studies directed toward the ultimate synthesis for ergot alkaloids. Yakugaku Zasshi 108(5), 361-380 (1988).