Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:52 UTC |
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Update date | 2020-09-17 15:41:02 UTC |
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Primary ID | FDB011884 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Quercitrin |
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Description | Quercitrin, also known as quercimelin or quercitronic acid, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. A quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. Quercitrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Quercitrin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Quercitrin is found, on average, in the highest concentration within a few different foods, such as lingonberries, american cranberries, and olives and in a lower concentration in common beans, tea, and welsh onions. Quercitrin has also been detected, but not quantified in, several different foods, such as guava, bilberries, common pea, apricots, and spearmints. This could make quercitrin a potential biomarker for the consumption of these foods. |
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CAS Number | 522-12-3 |
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Structure | |
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Synonyms | Synonym | Source |
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3,3',4',5,7-Pentahydroxyflavone-3-L-rhamnoside | ChEBI | 3-((6-Deoxy-alpha-L-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one | ChEBI | Luteolin 6-deoxy-alpha-L-mannopyranoside | ChEBI | Quercetin 3-L-rhamnoside | ChEBI | Quercetin 3-O-alpha-L-rhamnopyranoside | ChEBI | Quercetin 3-O-rhamnoside | ChEBI | Quercetin-3-L-rhamnoside | ChEBI | Quercimelin | ChEBI | Quercitronic acid | ChEBI | Quercitroside | ChEBI | 3-((6-Deoxy-a-L-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one | Generator | 3-((6-Deoxy-α-L-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one | Generator | Luteolin 6-deoxy-a-L-mannopyranoside | Generator | Luteolin 6-deoxy-α-L-mannopyranoside | Generator | Quercetin 3-O-a-L-rhamnopyranoside | Generator | Quercetin 3-O-α-L-rhamnopyranoside | Generator | Quercitronate | Generator | 3-O-a-L-Rhamnopyranosyloxy-3',4',5,7-tetrahydroxyflavone | HMDB | Flavone, 3,3',4',5, 7-pentahydroxy-, 3-rhamnoside | HMDB | Quercetin 3-O-alpha-L-rhamnoside | HMDB | Quercetin 3-O-alpha-rhamnopyranoside | HMDB | Quercetin 3-O-L-rhamnoside | HMDB | Quercetin 3-O-rhamnopyranoside | HMDB | Quercetin 3-rhamnoside | HMDB | Quercetin, 3-(6-deoxy-alpha-L-mannopyranoside) | HMDB | Quercetrin | HMDB | 3,3',4',5,7-Pentahydroxyflavone 3-alpha-L-rhamnoside | PhytoBank | 3,3',4',5,7-Pentahydroxyflavone 3-α-L-rhamnoside | PhytoBank | 3,3’,4’,5,7-Pentahydroxyflavone 3-α-L-rhamnoside | PhytoBank | 3-O-alpha-L-Rhamnopyranosylquercetin | PhytoBank | 3-O-α-L-Rhamnopyranosylquercetin | PhytoBank | 5,7,3',4'-Tetrahydroxyflavone 3-O-alpha-L-rhamnoside | PhytoBank | 5,7,3',4'-Tetrahydroxyflavone 3-O-α-L-rhamnoside | PhytoBank | 5,7,3’,4’-Tetrahydroxyflavone 3-O-α-L-rhamnoside | PhytoBank | Quercetin 3-O-α-L-rhamnoside | PhytoBank | Quercetin 3-O-α-rhamnopyranoside | PhytoBank | Quercetin 3-O-alpha-rhamnoside | PhytoBank | Quercetin 3-O-α-rhamnoside | PhytoBank | Quercetin 3-alpha-L-rhamnoside | PhytoBank | Quercetin 3-α-L-rhamnoside | PhytoBank | Quercetin 3-alpha-rhamnoside | PhytoBank | Quercetin 3-α-rhamnoside | PhytoBank | Quercetin rhamnoside | PhytoBank | Mannopyranoside, quercetin-3 6-deoxy-, α-L- | biospider | Quercetin 3-O-α-L-rhamnoside | biospider | Quercetin, 3-(6-deoxy-α-L-mannopyranoside) | biospider |
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Predicted Properties | |
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Chemical Formula | C21H20O11 |
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IUPAC name | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1 |
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InChI Key | OXGUCUVFOIWWQJ-HQBVPOQASA-N |
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Isomeric SMILES | C[C@@H]1O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O |
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Average Molecular Weight | 448.3769 |
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Monoisotopic Molecular Weight | 448.100561482 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavonoid glycosides |
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Direct Parent | Flavonoid-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-3-o-glycoside
- Hydroxyflavonoid
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Hexose monosaccharide
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- Catechol
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Pyran
- Monosaccharide
- Oxane
- Vinylogous acid
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Acetal
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 56.25%; H 4.50%; O 39.25% | DFC |
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Melting Point | Mp 250-252° (anhyd.) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.064 mg/mL at 16 oC | SEIDELL,A (1941) |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]15D -158 (c, 0.61 in MeOH) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Quercitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-053i-9202300000-146a66676d12880b9ed4 | Spectrum | Predicted GC-MS | Quercitrin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0002-9400018000-24e23b819c75a29c2092 | Spectrum | Predicted GC-MS | Quercitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0002-0024900000-74f4c7623d724538edfb | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0002-0000900010-b2ace14e72798df2daf5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0uk9-0095000000-fb1f4c76b153f376d777 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-00dl-0090000000-2e3d10965c5254c3204a | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 60V, Negative | splash10-006x-0090000000-b62d4ed30c4c4ccf8467 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0002-0024900000-74f4c7623d724538edfb | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0002-0000900010-b2ace14e72798df2daf5 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0uk9-0095000000-fb1f4c76b153f376d777 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-00dl-0090000000-2e3d10965c5254c3204a | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 60V, Negative | splash10-006x-0090000000-b62d4ed30c4c4ccf8467 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Negative | splash10-0udi-0149000000-45b606d3c459e3e5167a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0000900000-ed00185d5091572af122 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0002900000-87bfc2cd6f8980f4e934 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0009100000-8f8d7d2446ccce2143a7 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0029000000-88da6052a81a4903cd5e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0uk9-0194000000-078c0ba7b8b4b783e295 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udj-0169600000-924cb5834844dab2b7f5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0004900020-af3f3639e76a788d97ef | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0289000000-b59cf2bcc51db51c767d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0001900000-d8ec65a8565b9315fab4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0169400000-2a3b3a4a4e0531e878b9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0069400000-99e5a5dc152111b44e48 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udj-0197500000-0470e10f0b43724e37e9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udi-0009000000-91492ccad228cf14a895 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udi-0009000000-481378384c8cb997ee55 | 2017-09-14 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4444112 |
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ChEMBL ID | CHEMBL82242 |
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KEGG Compound ID | C01750 |
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Pubchem Compound ID | 5280459 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 295 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB33751 |
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CRC / DFC (Dictionary of Food Compounds) ID | HBN30-Z:HBN30-Z |
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EAFUS ID | Not Available |
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Dr. Duke ID | QUERCETIN-3-RHAMNOSIDE|QUERCITRIN|QUERCETRIN|QUERCETIN-3-O-RHAMNOSIDE|QUERCITIN-3-RHAMNOSIDE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00005374 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Quercitrin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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angiotensin converting enzyme inhibitor | 35457 | An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). | DUKE | aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | anti arrhythmic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti cataract | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti complementary | | | DUKE | anti edemic | | | DUKE | anti feedant | | | DUKE | anti flu | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti hemorrhagic | 50248 | Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. | DUKE | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti mutagenic | | | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti purpuric | 50177 | A drug used to treat or prevent skin disorders or for the routine care of skin. | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti staphylococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti thrombogenic | 50248 | Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | cardiotonic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | choleretic | | | DUKE | central nervous system depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | cyclooxygenase activator | | | DUKE | detoxicant | 50247 | Any protective agent counteracting or neutralizing the action of poisons. | DUKE | diuretic | 35498 | An agent that promotes the excretion of urine through its effects on kidney function. | DUKE | dye | 37958 | | DUKE | hemostat | | | DUKE | hepatotonic | | | DUKE | hypoglycemic | 35526 | A drug which lowers the blood glucose level. | DUKE | hypotensive | | | DUKE | Insectiphile | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | monoamine-oxidase-A inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | monoamine-oxidase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | paralytic | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | vasopressor | | | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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