An indole alkaloid with plant growth regulatory and anti-inflammatory activities
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Hypaphorine

Item No. 35228

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αS)-α-carboxy-N,N,N-trimethyl-1H-indole-3-ethanaminium, inner salt
CAS Number
487-58-1
Synonyms
  • L-Hypaphorine
  • (+)-Tryptophan
  • Tryptophan Betaine
Molecular Formula
C14H18N2O2
Formula Weight
246.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly solubleDMSO: Slightly solubleEthanol: Slightly solublePBS (pH 7.2): 5 mg/ml
λmax
220 nm
SMILES
C[N+](C)(C)[C@H](C([O-])=O)CC1=CNC2=CC=CC=C12
InChi Code
InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1
InChi Key
AOHCBEAZXHZMOR-ZDUSSCGKSA-N
Origin
Plant/Erythrina variegata
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    Cayman Chemical
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    Product Description

    Hypaphorine is an indole alkaloid that has been found in P. tinctorius and has plant growth regulatory and anti-inflammatory activities.1,2 It reverses inhibition of E. globulus seedling root growth induced by indole-3-acetic acid (IAA; Item No. 16954).1 Hypaphorine (12.5-50 µM) inhibits LPS-induced apoptosis in BEAS-2B bronchial epithelial cells.2 It decreases the severity of lung injury and bronchoalveolar fluid (BALF) neutrophil infiltration in a rat model of LPS-induced acute lung injury when administered at a dose of 10 mg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ditengou, F.A., and Lapeyrie, F. Hypaphorine from the ectomycorrhizal fungus Pisolithus tinctorius counteracts activities of indole-3-acetic acid and ethylene but not synthetic auxins in eucalypt seedlings. Mol. Plant Microbe Interact. 13(2), 151-158 (2000).

    2. Ding, Y.-H., Miao, R.-X., and Zhang, Q. Hypaphorine exerts anti-inflammatory effects in sepsis induced acute lung injury via modulating DUSP1/p38/JNK pathway. Kaohsiung J. Med. Sci. 37(10), 883-893 (2021).