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| {{chembox | {{chembox | ||
| | verifiedrevid = |
| verifiedrevid = 444328279 | ||
| | |
| Name = Isoquercetin | ||
| | |
| ImageFile = Isoquercitin.svg | ||
| | |
| ImageSize = 250px | ||
| | |
| ImageName = Isoquercitrin structure | ||
| | IUPACName = 3-(β-<small>D</small>-Glucopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone | |||
| | IUPACName = 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4, | |||
| 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] |
| SystematicName = 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{oxy}-4''H''-1-benzopyran-4-one | ||
| | |
| OtherNames= Isoquercitroside<br>Isoquercitrin<br>Isoquercetin<br>Trifoliin<br>Isotrifolin<br>Trifoliin A<br>Isohyperoside<br>Isotrifoliin<br>Quercetin-3-glucoside<br>Quercetin-3-''O''-glucoside<br>Quercetin 3-''O''-β-<small>D</small>-glucopyranoside | ||
| | |
|Section1={{Chembox Identifiers | ||
| | CASNo_Ref = {{cascite|correct|CAS}} | |||
| | CASNo = 21637-25-2 | |||
| | |
| CASNo = 482-35-9 | ||
| | UNII_Ref = {{fdacite|correct|FDA}} | |||
| ⚫ | | |
||
| | UNII = 6HN2PC637T | |||
| | KEGG_Ref = {{keggcite|correct|kegg}} | |||
| | KEGG = C05623 | |||
| | PubChem = 5280804 | |||
| | ChemSpiderID = 4444361 | |||
| ⚫ | | SMILES = C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O4((((O4)CO)O)O)O)O)O | ||
| | InChI = 1/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1 | |||
| | InChIKey = OVSQVDMCBVZWGM-QSOFNFLRBX | |||
| | StdInChI = 1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1 | |||
| | StdInChIKey = OVSQVDMCBVZWGM-QSOFNFLRSA-N | |||
| }} | }} | ||
| | |
|Section2={{Chembox Properties | ||
| | C=21 | H=20 | O=12 | |||
| | Formula = C<sub>21</sub>H<sub>20</sub>O<sub>12</sub> | |||
| | Density = | |||
| | MolarMass = 464.37 g/mol | |||
| ⚫ | | MeltingPt = | ||
| | ExactMass = 464.095476 u | |||
| | |
| BoilingPt = | ||
| ⚫ | | |
||
| | BoilingPt = | |||
| }} | }} | ||
| }} | }} | ||
| '''Isoquercetin''', '''isoquercitrin''' or '''isotrifoliin'''<ref>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/5280804#section=Top |title=Isoquercetin |publisher=] |access-date=2018-09-11}}</ref> is a ], a type of chemical compound. It is the 3-''O''-] of ]. Isoquercitrin can be isolated from various plant species including '']'' (])<ref>{{Cite journal |vauthors=Singh UP, Singh DP, Singh M, etal |title=Characterization of phenolic compounds in some Indian mango cultivars |journal=International Journal of Food Sciences and Nutrition |volume=55 |issue=2 |pages=163–9 |year=2004 |pmid=14985189 |doi=10.1080/09637480410001666441}}</ref> and '']'' (the Noble rhubarb). It is also present in the leaves of '']'', '']'' (]).<ref name="pmid18997283">{{cite journal| author=Panda S, Kar A| title=Antidiabetic and antioxidative effects of ''Annona squamosa'' leaves are possibly mediated through quercetin-3-O-glucoside | journal=BioFactors | year= 2007 | volume= 31 | issue= 3-4 | pages= 201–210 | pmid=18997283 |doi=10.1002/biof.5520310307}}</ref><ref>{{Cite journal | doi = 10.1021/jf020926l | title = Simultaneous determination of all polyphenols in vegetables, fruits, and teas | year = 2003 | last1 = Sakakibara | first1 = H | last2 = Honda | first2 = Y | last3 = Nakagawa | first3 = S | last4 = Ashida | first4 = H | last5 = Kanazawa | first5 = K | journal = Journal of Agricultural and Food Chemistry | volume = 51 | issue = 3 | pages = 571–81 | pmid = 12537425}}</ref> and '']''<ref>C. Brevis, M. Quezada, P. Bustamante, L. Carrasco, A. Ruiz, S. Donoso, Huevil (Vestia foetida) poisoning of cattle in Chile ''The Veterinary record'' 156(14):452-3 May 2005</ref> | |||
| '''Isoquercitin''' is a chemical compound. It can be isolated from ]es and from '']'', the Noble rhubarb or Sikkim rhubarb, a giant herbaceous plant native to the Himalaya. Quercetin glycosides are also present in tea<ref></ref>. | |||
| ⚫ | == Spectral data == | ||
| It is the 3-O-] of ]. | |||
| ⚫ | The ] for isoquercetin is 254.8 and 352.6 ]. | ||
| == Potential clinical uses == | |||
| ⚫ | ==Spectral |
||
| Isoquercetin is presently being investigated for prevention of ] in selected cancer patients<ref></ref> and as an anti-] agent in kidney cancer patients treated with ].<ref></ref> | |||
| {| border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;" | |||
| There is a single case report of its use in the successful treatment of ], a difficult to treat pruritic eruption of the skin.<ref>{{cite journal| | |||
| ! {{chembox header}} | ] | |||
| title = Use of Isoquercetin in the Treatment of Prurigo Nodularis |url=http://jddonline.com/articles/dermatology/S1545961617P1156X/1 |date=November 2017 | volume=16 | issue=11 | pages=1156–1158 |journal=Journal of Drugs in Dermatology |first1=Christine M. |last1=Pennesi |first2=John |last2=Neely |first3=Ames G. |last3=Marks Jr. |first4=S. |last4=Alison Basak}}</ref> | |||
| |- | |||
| | ] | |||
| ⚫ | |||
| |- | |||
| | ] | |||
| | ? | |||
| |- | |||
| However it belongs to the ] categories of chemicals.<ref>{{Cite journal | journal = Nature | year = 2014| volume = 513| issue = 7519 | pages = 481–483 | title = Chemistry: Chemical con artists foil drug discovery |author1=J Baell |author2=M A Walters | doi = 10.1038/513481a |name-list-style=amp | pmid= 25254460 | doi-access = free }}</ref> | |||
| ! {{chembox header}} | ] | |||
| |- | |||
| | Major absorption bands | |||
| | ? cm<sup>−1</sup> | |||
| |- | |||
| ⚫ | == References == | ||
| ! {{chembox header}} | ] | |||
| |- | |||
| | ] <!-- Link to image of spectrum --> | |||
| |- | |||
| | ] <!-- Link to image of spectrum --> | |||
| |- | |||
| | Other NMR data <!-- Insert special data e.g. <sup>19</sup>F chem. shifts, omit if not used --> | |||
| |- | |||
| ! {{chembox header}} | ] | |||
| |- | |||
| | Masses of <br>main fragments | |||
| | <!-- Give list of major fragments --> | |||
| |- | |||
| |} | |||
| ⚫ | ==References== | ||
| {{Reflist}} | {{Reflist}} | ||
| == See also == | |||
| ⚫ | {{flavonol}} | ||
| * ] | |||
| ⚫ | {{flavonol|state=collapsed}} | ||
| ⚫ | ] | ||
| ] | |||
| ⚫ | ] | ||
| {{Natural-phenol-stub}} | |||
| ] | |||
Latest revision as of 18:15, 20 August 2024
 | |
| Names | |
|---|---|
| IUPAC name 3-(β-D-Glucopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone | |
| Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{oxy}-4H-1-benzopyran-4-one | |
| Other names
Isoquercitroside Isoquercitrin Isoquercetin Trifoliin Isotrifolin Trifoliin A Isohyperoside Isotrifoliin Quercetin-3-glucoside Quercetin-3-O-glucoside Quercetin 3-O-β-D-glucopyranoside | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.123.856 
|
| KEGG | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C21H20O12 |
| Molar mass | 464.379 g·mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
| |
Isoquercetin, isoquercitrin or isotrifoliin is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including Mangifera indica (mango) and Rheum nobile (the Noble rhubarb). It is also present in the leaves of Annona squamosa, Camellia sinensis (tea). and Vestia foetida
Spectral data
The lambda-max for isoquercetin is 254.8 and 352.6 nm.
Potential clinical uses
Isoquercetin is presently being investigated for prevention of thromboembolism in selected cancer patients and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.
There is a single case report of its use in the successful treatment of prurigo nodularis, a difficult to treat pruritic eruption of the skin.
However it belongs to the PAINS (Pan-assay interference compounds) categories of chemicals.
References
- "Isoquercetin". PubChem. Retrieved 2018-09-11.
- Singh UP, Singh DP, Singh M, et al. (2004). "Characterization of phenolic compounds in some Indian mango cultivars". International Journal of Food Sciences and Nutrition. 55 (2): 163–9. doi:10.1080/09637480410001666441. PMID 14985189.
- Panda S, Kar A (2007). "Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-O-glucoside". BioFactors. 31 (3–4): 201–210. doi:10.1002/biof.5520310307. PMID 18997283.
- Sakakibara, H; Honda, Y; Nakagawa, S; Ashida, H; Kanazawa, K (2003). "Simultaneous determination of all polyphenols in vegetables, fruits, and teas". Journal of Agricultural and Food Chemistry. 51 (3): 571–81. doi:10.1021/jf020926l. PMID 12537425.
- C. Brevis, M. Quezada, P. Bustamante, L. Carrasco, A. Ruiz, S. Donoso, Huevil (Vestia foetida) poisoning of cattle in Chile The Veterinary record 156(14):452-3 May 2005
- NCT02195232
- NCT02446795
- Pennesi, Christine M.; Neely, John; Marks Jr., Ames G.; Alison Basak, S. (November 2017). "Use of Isoquercetin in the Treatment of Prurigo Nodularis". Journal of Drugs in Dermatology. 16 (11): 1156–1158.
- J Baell & M A Walters (2014). "Chemistry: Chemical con artists foil drug discovery". Nature. 513 (7519): 481–483. doi:10.1038/513481a. PMID 25254460.