Herbacetin: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~404631640~~
			\| Watchedfields = changed
		⚫	\| verifiedrevid = 423602723
	\| Name = Herbacetin		\| Name = Herbacetin
	\| ImageFile = Herbacetin.~~PNG~~		\| ImageFile = Herbacetin.svg
		⚫	\| ImageAlt = Chemical structure of herbacetin
	\| ImageSize = 200px
			\| ImageFile1 = Herbacetin-3D-balls.png
⚫	\| ~~ImageName~~ = Chemical structure of herbacetin
			\| ImageAlt1 = Ball-and-stick model of the herbacetin molecule
⚫	\| ~~IUPACName~~ = 3,5,7,8-~~tetrahydroxy~~-2-(4-hydroxyphenyl)~~chromen~~-4-one
			\| IUPACName = 3,4′,5,7,8-Pentahydroxyflavone
		⚫	\| SystematicName = 3,5,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-4''H''-1-benzopyran-4-one
	\| OtherNames = 8-Hydroxykaempferol<!-- <br> -->		\| OtherNames = 8-Hydroxykaempferol<!-- <br> -->
	\|Section1= {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo = 527-95-7		\| CASNo = 527-95-7
	\| CASNo_Ref =		\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| CASOther =

			\| UNII = 736854V2KE
			\| CASNoOther =
	\| PubChem = 5280544		\| PubChem = 5280544
			\| ChEBI = 27673
	\| SMILES = C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O		\| SMILES = C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| InChI =
			\| ChemSpiderID = 4444174
			\| 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
			\| InChIKey = ZDOTZEDNGNPOEW-UHFFFAOYAP
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 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
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = ZDOTZEDNGNPOEW-UHFFFAOYSA-N
	\| MeSHName =		\| MeSHName =
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=15 \| H=10 \| O=7
	\| Formula = C<sub>15</sub>H<sub>10</sub>O<sub>7</sub>
	\| MolarMass = 302.23 g/mol
	\| ExactMass = 302.042653 u
	\| Appearance =		\| Appearance =
	\| Density =		\| Density = 1.799 g/mL
	\| MeltingPt = ~~<!-- °C -->~~		\| MeltingPt =
	\| BoilingPt = ~~<!-- °C -->~~		\| BoilingPt =
	\| Solubility =		\| Solubility =
	}}		}}
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	'''Herbacetin''' is a ], a type of flavonoid.		'''Herbacetin''' is a ], a type of flavonoid.

			== Glycosides ==
⚫	==~~Glycoside~~ ~~and other~~ related compounds ==
	] can be isolated from ] hulls.<ref></ref>		] can be isolated from ] hulls.<ref>{{Cite journal \| last1 = Struijs \| first1 = K. \| last2 = Vincken \| first2 = J. P. \| last3 = Verhoef \| first3 = R. \| last4 = Van Oostveen-Van Casteren \| first4 = W. H. M. \| last5 = Voragen \| first5 = A. G. J. \| last6 = Gruppen \| first6 = H. \| doi = 10.1016/j.phytochem.2006.10.022 \| title = The flavonoid herbacetin diglucoside as a constituent of the lignan macromolecule from flaxseed hulls \| journal = Phytochemistry \| volume = 68 \| issue = 8 \| pages = 1227–1235 \| year = 2007 \| pmid = 17141814}}</ref>

			] is a herbacetin ] found in '']'' species.<ref>{{Cite journal \| last1 = Li \| first1 = T. \| last2 = Zhang \| first2 = H. \| doi = 10.1248/cpb.56.807 \| title = 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 \| journal = Chemical & Pharmaceutical Bulletin \| volume = 56 \| issue = 6 \| pages = 807–14 \| year = 2008 \| pmid = 18520085\| doi-access = free }}</ref>

		⚫	== Other related compounds ==
	], a ], is the product of the oxidative coupling of ] with the 7,8-dihydroxy grouping of herbacetin. It can be found in the rhizome of '']''.<ref></ref>		], a ], is the product of the oxidative coupling of ] with the 7,8-dihydroxy grouping of herbacetin. It can be found in the rhizome of '']''.<ref>{{Cite journal \| last1 = Zapesochnaya \| first1 = G. G. \| last2 = Kurkin \| first2 = V. A. \| doi = 10.1007/BF00579955 \| title = The flavonoids of the rhizomes ofRhodiola rosea. II. A flavonolignan and glycosides of herbacetin \| journal = Chemistry of Natural Compounds \| volume = 19 \| pages = 21–29 \| year = 1983 \| s2cid = 7656479 }}</ref>

	==References==		==References==
	{{~~reflist~~}}		{{Reflist}}

	{{flavonol}}		{{flavonol}}
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	]		]

	{{~~Natural-phenol~~-stub}}		{{aromatic-stub}}

Latest revision as of 17:18, 2 May 2023

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

Herbacetin diglucoside can be isolated from flaxseed hulls.

Rhodionin is a herbacetin rhamnoside found in Rhodiola species.

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.

References

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

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Conjugates of quercetin

Sulfates

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

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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