A phenol with diverse biological activities
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Chebulic Acid

Item No. 11829

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S)-[(3S,4S)-3-carboxy-3,4-dihydro-5,6,7-trihydroxy-1-oxo-1H-2-benzopyran-4-yl]-butanedioic acid
CAS Number
23725-05-5
Synonyms
  • (–)-Chebulic Acid
Molecular Formula
C14H12O11
Formula Weight
356.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Methanol: soluble
λmax
225, 287 nm
SMILES
OC1=C(O)C(O)=CC2=C1[C@@]([C@H](CC(O)=O)C(O)=O)([H])[C@@H](C(O)=O)OC2=O
InChi Code
InChI=1S/C14H12O11/c15-5-1-4-7(10(19)9(5)18)8(3(12(20)21)2-6(16)17)11(13(22)23)25-14(4)24/h1,3,8,11,15,18-19H,2H2,(H,16,17)(H,20,21)(H,22,23)/t3?,8-,11?/m0/s1
InChi Key
COZMWVAACFYLBI-CFHUBPRQSA-N
Origin
Plant/Chebulae Fructus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    5 mg

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    Cayman Chemical
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    Product Description

    Chebulic acid is a phenol that has been found in T. chebular and has diverse biological activities.1,2,3 It reduces production of reactive oxygen species (ROS) in human umbilical vein endothelial cells (HUVECs) induced by glyceraldehyde-related advanced glycation end products (glycer-AGEs) when used at a concentration of 100 µg/ml.1 Chebulic acid reduces glycer-AGE-induced adhesion of HUVECs to THP-1 monocytes. It induces Nrf2 nuclear translocation and glutathione (GSH) synthesis and inhibits glycer-AGE-induced collagen accumulation, a marker of fibrosis, in LX-2 hepatic stellate cells.2 In vivo, chebulic acid (25 and 50 mg/kg) increases serum insulin levels and reduces blood urea nitrogen levels, proteinuria, albuminuria, and serum glucose levels in a diabetic rat model of ischemia-reperfusion-induced nephropathy.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lee, H.-S., Koo, Y.-C., Suh, H.J., et al. Preventive effects of chebulic acid isolated from Terminalia chebula on advanced glycation endproduct-induced endothelial cell dysfunction. J. Ethnopharmacol. 131(3), 567-574 (2010).

    2. Koo, Y.-C., Pyo, M.C., Nam, M.-H., et al. Chebulic acid prevents hepatic fibrosis induced by advanced glycation end-products in LX-2 cell by modulating Nrf2 translocation via ERK pathway. Toxicol. In Vitro 34, 8-15 (2016).

    3. Silawat, N., and Gupta, V.B. Chebulic acid attenuates ischemia reperfusion induced biochemical alteration in diabetic rats. Pharm. Biol. 51(1), 23-29 (2013).