Patuletin: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
			\| Watchedfields = changed
			\| verifiedrevid = 401011214
	\| Name = Patuletin		\| Name = Patuletin
	\| ImageFile = Patuletin.~~PNG~~		\| ImageFile = Patuletin.svg
	\| ImageSize = 200px
	\| ImageName = Chemical structure of patuletin		\| ImageName = Chemical structure of patuletin
	\| IUPACName = ~~2-(~~3,~~4-dihydroxyphenyl)-3~~,5,7-~~trihydroxy~~-6-~~methoxychromen-4-one~~		\| IUPACName = 3,3′,4′,5,7-Pentahydroxy-6-methoxyflavone
			\| SystematicName = 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4''H''-1-benzopyran-4-one
	\| OtherNames = 6-Methoxyquercetin<br>Quercetagetin 6-methyl ether<br>2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone		\| OtherNames = 6-Methoxyquercetin<br>Quercetagetin 6-methyl ether<br>2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone
	\|Section1= {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo = 519-96-0		\| CASNo = 519-96-0
	\| CASNo_Ref =		\| CASNo_Ref = {{cascite\|correct\|??}}
	\| ~~CASOther~~ =		\| CASNoOther =
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 9BNM33N01N
	\| PubChem = 5281678		\| PubChem = 5281678
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL = 465155
	\| SMILES = COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O)O		\| SMILES = COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O)O
	\| ~~InChI~~ =		\| EINECS = 208-280-8
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| ChemSpiderID = 4444997
			\| InChI = 1/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3
			\| InChIKey = JMIFIYIEXODVTO-UHFFFAOYAR
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = JMIFIYIEXODVTO-UHFFFAOYSA-N
			\| RTECS =
	\| MeSHName =		\| MeSHName =
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\| ChEBI = 75164
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=16 \| H=12 \| O=8
	\| Formula = C<sub>16</sub>H<sub>12</sub>O<sub>8</sub>
	\| MolarMass = 332.26 g/mol
	\| ExactMass = 332.053217 u
	\| Appearance =		\| Appearance =
	\| Density =		\| Density =
	\| MeltingPt = ~~<!-- °C -->~~		\| MeltingPt =
	\| BoilingPt = ~~<!-- °C -->~~		\| BoilingPt =
	\| Solubility =		\| Solubility =
	}}		}}
	}}		}}
	'''Patuletin''' is an ]. It can be found in the genus '']''.<ref></ref>		'''Patuletin''' is an ]. It can be found in the genus '']''.<ref>{{Cite journal \| last1 = Bate-Smith \| first1 = E. C. \| last2 = Harborne \| first2 = J. B. \| doi = 10.1016/S0031-9422(00)86351-7 \| title = Quercetagetin and patuletin in Eriocaulon \| journal = Phytochemistry \| volume = 8 \| issue = 6 \| pages = 1035 \| year = 1969 \| bibcode = 1969PChem...8.1035B }}</ref>

	==Glycosides==		== Glycosides ==
	Patuletin glycosides can be found in '']''.<ref></ref>		Patuletin glycosides can be found in '']''.<ref>{{Cite journal \| last1 = Smith \| first1 = D. M. \| last2 = Glennie \| first2 = C. W. \| last3 = Harborne \| first3 = J. B. \| doi = 10.1016/S0031-9422(00)97361-8 \| title = Identification of eupalitin, eupatolitin and patuletin glycosides in Ipomopsis aggregata \| journal = Phytochemistry \| volume = 10 \| issue = 12 \| pages = 3115 \| year = 1971 \| bibcode = 1971PChem..10.3115S }}</ref>

	] can be isolated from the aerial parts of '']''.<ref></ref>		] can be isolated from the aerial parts of '']''.<ref>{{Cite journal \| last1 = Lin \| first1 = L. \| last2 = Qiu \| first2 = S. \| last3 = Lindenmaier \| first3 = M. \| last4 = He \| first4 = X. \| last5 = Featherstone \| first5 = T. \| last6 = Cordell \| first6 = G. A. \| doi = 10.1076/phbi.40.2.92.5839 \| title = Patuletin-3-O-Rutinoside from the Aerial Parts of Echinacea angustifolia \| journal = Pharmaceutical Biology \| volume = 40 \| issue = 2 \| pages = 92 \| year = 2002 \| s2cid = 84855629 }}</ref>

	]s can be isolated from '']''.<ref>~~</ref>~~		]s can be isolated from '']''.<ref>{{Cite journal
			\| last1 = Costa \| first1 = S. S.
⚫	==References==
			\| last2 = Jossang \| first2 = A.
	{{reflist}}
			\| last3 = Bodo \| first3 = B.
			\| last4 = Souza \| first4 = M. L. M.
			\| last5 = Moraes \| first5 = V. L. G.
			\| title = Patuletin Acetylrhamnosides from Kalanchoe brasiliensis as Inhibitors of Human Lymphocyte Proliferative Activity
			\| doi = 10.1021/np50113a005
			\| journal = Journal of Natural Products
			\| volume = 57
			\| issue = 11
			\| pages = 1503–1510
			\| year = 1994
			\| pmid = 7853000
			}}</ref>

		⚫	== References ==
			{{Reflist}}

	{{flavonol}}		{{flavonol}}

	]		]
	]
	]
	]


	{{~~polyphenol~~-stub}}		{{aromatic-stub}}

Latest revision as of 03:07, 24 December 2024

Patuletin
Names

IUPAC name 3,3′,4′,5,7-Pentahydroxy-6-methoxyflavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-1-benzopyran-4-one
Other names 6-Methoxyquercetin Quercetagetin 6-methyl ether 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone
Identifiers
CAS Number	519-96-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75164
ChEMBL	ChEMBL465155
ChemSpider	4444997
ECHA InfoCard	100.007.529
EC Number	208-280-8
PubChem CID	5281678
UNII	9BNM33N01N
CompTox Dashboard (EPA)	DTXSID20199864
InChI InChI=1S/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3Key: JMIFIYIEXODVTO-UHFFFAOYSA-N InChI=1/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3Key: JMIFIYIEXODVTO-UHFFFAOYAR
SMILES COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O)O
Properties
Chemical formula	C₁₆H₁₂O₈
Molar mass	332.264 g·mol
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

Patuletin is an O-methylated flavonol. It can be found in the genus Eriocaulon.

Glycosides

Patuletin glycosides can be found in Ipomopsis aggregata.

Patuletin-3-O-rutinoside can be isolated from the aerial parts of Echinacea angustifolia.

Patuletin acetylrhamnosides can be isolated from Kalanchoe brasiliensis.

References

Bate-Smith, E. C.; Harborne, J. B. (1969). "Quercetagetin and patuletin in Eriocaulon". Phytochemistry. 8 (6): 1035. Bibcode:1969PChem...8.1035B. doi:10.1016/S0031-9422(00)86351-7.
Smith, D. M.; Glennie, C. W.; Harborne, J. B. (1971). "Identification of eupalitin, eupatolitin and patuletin glycosides in Ipomopsis aggregata". Phytochemistry. 10 (12): 3115. Bibcode:1971PChem..10.3115S. doi:10.1016/S0031-9422(00)97361-8.
Lin, L.; Qiu, S.; Lindenmaier, M.; He, X.; Featherstone, T.; Cordell, G. A. (2002). "Patuletin-3-O-Rutinoside from the Aerial Parts of Echinacea angustifolia". Pharmaceutical Biology. 40 (2): 92. doi:10.1076/phbi.40.2.92.5839. S2CID 84855629.
Costa, S. S.; Jossang, A.; Bodo, B.; Souza, M. L. M.; Moraes, V. L. G. (1994). "Patuletin Acetylrhamnosides from Kalanchoe brasiliensis as Inhibitors of Human Lymphocyte Proliferative Activity". Journal of Natural Products. 57 (11): 1503–1510. doi:10.1021/np50113a005. PMID 7853000.

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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