Herbacetin - Misplaced Pages

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Herbacetin
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
CAS Number	527-95-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27673
ChemSpider	4444174
ECHA InfoCard	100.237.124
PubChem CID	5280544
UNII	736854V2KE
CompTox Dashboard (EPA)	DTXSID70415061
InChI 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/h1-5,16-19,21HKey: ZDOTZEDNGNPOEW-UHFFFAOYSA-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/h1-5,16-19,21HKey: ZDOTZEDNGNPOEW-UHFFFAOYAP
SMILES C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O
Properties
Chemical formula	C₁₅H₁₀O₇
Molar mass	302.238 g·mol
Density	1.799 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Herbacetin is a flavonol, a type of flavonoid.

Glycosides

Rhodionin is a herbacetin rhamnoside found in Rhodiola species.

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.

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.
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.
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.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Glycosides of myricetin

Conjugates of quercetin

Sulfates

Glycosides

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin
Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Aglycones	Karanjin
Glycosides	Pongamoside A, B and C

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

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