Chebulic acid

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Chebulic acid
Chebulic acid, according to Lee, 2010.^[1]
Chebulic acid, according to Klika, 2004.^[2]
IUPAC name (2R)-2-[(3S)-3-carboxy-5,6,7-trihydroxy-1-oxo-3,4-ihydroisochromen-4-yl]butanedioic acid
Other names Chebuloyl
Identifiers
CAS number	23725-05-5^Y
PubChem	25255065
ChemSpider	27470963^N
Jmol-3D images	{{#if:c1c2c(c(c(c1O)O)O)[C@@H]([C@H](OC2=O)C(=O)O)[C@H](CC(=O)O)C(=O)O\|Image 1
SMILES c1c2c(c(c(c1O)O)O)[C@@H]([C@H](OC2=O)C(=O)O)[C@H](CC(=O)O)C(=O)O
InChI 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^N Key: COZMWVAACFYLBI-XJEVXTIOSA-N^N InChI=1/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 Key: COZMWVAACFYLBI-XJEVXTIOBW
Properties
Molecular formula	C₁₄H₁₂O₁₁
Molar mass	356.23 g/mol
Appearance	Brown powder
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Chebulic acid is a phenolic compound isolated from the ripe fruits of Terminalia chebula.^[3]

This compound possesses an isomer, neochebulic acid.

Chebulic acid is a component of transformed ellagitannins such as chebulagic acid or chebulinic acid.

References

↑ Lee, H. S.; Koo, Y. C.; Suh, H. J.; Kim, K. Y.; Lee, K. W. (2010). "Preventive effects of chebulic acid isolated from Terminalia chebula on advanced glycation endproduct-induced endothelial cell dysfunction". Journal of Ethnopharmacology 131 (3): 567–574. doi:10.1016/j.jep.2010.07.039. PMID 20659546.
↑ The structural and conformational analyses and antioxidant activities of chebulinic acid and its thrice-hydrolyzed derivative, 2,4-chebuloyl-β-D-glucopyranoside, isolated from the fruit of Terminalia chebula. Karel D. Klika, Ammar Saleem, Jari Sinkkonen, Marja Kähkönen, Jyrki Loponen, Petri Tähtinen and Kalevi Pihlaja, ARKIVOC 2004 (vii) 83-105
↑ Lee, H. S.; Jung, S. H.; Yun, B. S.; Lee, K. W. (2006). "Isolation of chebulic acid from Terminalia chebula Retz. And its antioxidant effect in isolated rat hepatocytes". Archives of Toxicology 81 (3): 211–218. doi:10.1007/s00204-006-0139-4. PMID 16932919.

Aglycones

Lactones

Monomers

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

Transformed ellagitannins

molecules with chebulic acid	Chebulagic acid Chebulinic acid

molecules with Elaeocarpusinic acid	Elaeocarpusin Helioscopin B Mallojaponin (1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose)

Oligomers

Dimers: Agrimoniin; Cornusiin E (dimer of tellimagrandin II); Lambertianin A and B; Nobotanin B; Roburin A; Sanguiin H-6

Other

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