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Chebulinic acid

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Chebulinic acid
Names
Other names 1,3,6-Tri-O-galloyl-2,4-chebuloyl-β-D-glucopyranoside
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49, 50)/t14-,22+,24-,30-,31+,33-,34+,41-/m0/s1Key: YGVHOSGNOYKRIH-FJPMMHPYSA-N
SMILES
  • C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C(C(C(=O)O3)CC(=O)O)C(C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
Properties
Chemical formula C41H32O27
Molar mass 956.680 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

Chebulinic acid is an ellagitannin found in the seeds of Euphoria longana, in the fruits of Terminalia chebula or in the leaves of T. macroptera.

References

  1. Karel D. Klika, Ammar Saleem, Jari Sinkkonen, Marja Kähkönen, Jyrki Loponen, Petri Tähtinen and Kalevi Pihlaja (2004). "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". Arkivoc. vii: 83–105.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Han, Quanbin; Song, Jingzheng; Qiao, Chunfeng; Wong, Lina; Xu, Hongxi (2006). "Preparative isolation of hydrolysable tannins chebulagic acid and chebulinic acid from Terminalia chebula by high-speed counter-current chromatography". Journal of Separation Science. 29 (11): 1653–1657. doi:10.1002/jssc.200600089. PMID 16922284.
Types of ellagitannins
Moieties
Lactones
Monomers
C-glycosidic ellagitannins
Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)
Transformed ellagitannins
molecules with chebulic acid
molecules with Elaeocarpusinic acid
Oligomers
Dimers
Agrimoniin
Cornusiin E (dimer of tellimagrandin II)
Lambertianin A and B
Nobotanin B
Roburin A, B, C and D
Sanguiin H-6
Trimers
Lambertianin C
Raspberry ellagitannin
Tetramers
Lambertianin D
Nobotanin S
Pentamer
Melastoflorin A
Other
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