Herbacetin
Chemical structure of herbacetin
Ball-and-stick model of the herbacetin molecule
Names
IUPAC name
3,4′,5,7,8-Pentahydroxyflavone
Systematic IUPAC name
3,5,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
8-Hydroxykaempferol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.237.124 Edit this at Wikidata
UNII
  • InChI=1S/C15H10O7/c16-7-3-1-6(2-4-7)14-13(21)12(20)10-8(17)5-9(18)11(19)15(10)22-14/h1-5,16-19,21H ☒N
    Key: ZDOTZEDNGNPOEW-UHFFFAOYSA-N ☒N
  • InChI=1/C15H10O7/c16-7-3-1-6(2-4-7)14-13(21)12(20)10-8(17)5-9(18)11(19)15(10)22-14/h1-5,16-19,21H
    Key: ZDOTZEDNGNPOEW-UHFFFAOYAP
  • C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O
Properties
C15H10O7
Molar mass 302.238 g·mol−1
Density 1.799 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Herbacetin is a flavonol, a type of flavonoid.

Glycosides

Herbacetin diglucoside can be isolated from flaxseed hulls.[1]

Rhodionin is a herbacetin rhamnoside found in Rhodiola species.[2]

Other related compounds

Rhodiolin, a flavonolignan, is the product of the oxidative coupling of coniferyl alcohol with the 7,8-dihydroxy grouping of herbacetin. It can be found in the rhizome of Rhodiola rosea.[3]

References

  1. ^ Struijs, K.; Vincken, J. P.; Verhoef, R.; Van Oostveen-Van Casteren, W. H. M.; Voragen, A. G. J.; Gruppen, H. (2007). "The flavonoid herbacetin diglucoside as a constituent of the lignan macromolecule from flaxseed hulls". Phytochemistry. 68 (8): 1227–1235. doi:10.1016/j.phytochem.2006.10.022. PMID 17141814.
  2. ^ Li, T.; Zhang, H. (2008). "Identification and Comparative Determination of Rhodionin in Traditional Tibetan Medicinal Plants of Fourteen Rhodiola Species by High-Performance Liquid Chromatography-Photodiode Array Detection and Electrospray Ionization-Mass Spectrometry". Chemical & Pharmaceutical Bulletin. 56 (6): 807–14. doi:10.1248/cpb.56.807. PMID 18520085.
  3. ^ Zapesochnaya, G. G.; Kurkin, V. A. (1983). "The flavonoids of the rhizomes ofRhodiola rosea. II. A flavonolignan and glycosides of herbacetin". Chemistry of Natural Compounds. 19: 21–29. doi:10.1007/BF00579955. S2CID 7656479.
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