Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:12:50 UTC |
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Update date | 2019-11-26 03:14:11 UTC |
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Primary ID | FDB017095 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Quercetin 4'-glucoside |
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Description | Quercetin 4'-glucoside, also known as spiraein or spiraeoside, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Quercetin 4'-glucoside is found, on average, in the highest concentration within a few different foods, such as garden onions (Allium cepa), shallots (Allium ascalonicum), and garden onion (var.). Quercetin 4'-glucoside has also been detected, but not quantified in, sweet cherries (Prunus avium) and yali pears (Pyrus × bretschneideri). This could make quercetin 4'-glucoside a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Quercetin 4'-glucoside. |
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CAS Number | 20229-56-5 |
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Structure | |
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Synonyms | Synonym | Source |
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Spiraein | ChEBI | Spiraeoside | ChEBI | Quercetin-4'-glucoside | MeSH | Quercetin 4'-O-beta-D-glucopyranoside | HMDB | Quercetin 4'-O-beta-D-glucoside | HMDB | Quercetin 4'-O-glucoside | HMDB | Spiraeosid | HMDB | Spireoside (6ci,7ci,8ci) | HMDB | Quercetin 4'-O-b-D-glucopyranoside | Generator | Quercetin 4'-O-β-D-glucopyranoside | Generator | 3,3',4',5,7-Pentahydroxyflavone 4'-O-b-D-glucopyranoside | manual | Quercetin 4'-glucoside | db_source | Spireoside (6CI,7CI,8CI) | manual |
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Predicted Properties | |
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Chemical Formula | C21H20O12 |
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IUPAC name | 3,5,7-trihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-2-1-7(3-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1 |
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InChI Key | OIUBYZLTFSLSBY-HMGRVEAOSA-N |
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Isomeric SMILES | OC[C@H]1O[C@@H](OC2=CC=C(C=C2O)C2=C(O)C(=O)C3=C(O2)C=C(O)C=C3O)[C@H](O)[C@@H](O)[C@@H]1O |
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Average Molecular Weight | 464.3763 |
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Monoisotopic Molecular Weight | 464.095476104 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. |
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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 O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid o-glycoside
- Flavonoid-4p-o-glycoside
- 3-hydroxyflavone
- Hydroxyflavonoid
- 3'-hydroxyflavonoid
- 3-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Phenolic glycoside
- Hexose monosaccharide
- O-glycosyl compound
- Glycosyl compound
- Chromone
- Benzopyran
- 1-benzopyran
- Phenol ether
- Phenoxy compound
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Pyranone
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Pyran
- Oxane
- Monosaccharide
- Vinylogous acid
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Acetal
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Primary alcohol
- 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 | 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 54.32%; H 4.34%; O 41.34% | DFC |
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Melting Point | Mp 240-241° (209-210°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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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]17D -69 (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 | Quercetin 4'-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0w31-7804900000-dac1de5f80e977a6a3f6 | Spectrum | Predicted GC-MS | Quercetin 4'-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014r-3620009000-b9a475a5880bcb322222 | Spectrum | Predicted GC-MS | Quercetin 4'-glucoside, 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 | splash10-001i-0190000000-33aab7c5c534e3bd93d2 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0udi-0209000000-8d0c8eda18dc8cceda25 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-0udi-0936000000-ead01d21177722db0c04 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 60V, Negative | splash10-0udi-0942000000-fa589cb74705f9065b0e | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-03di-0002900001-4dfb6b7d47117fdc7cd5 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0udi-0009100000-8535cabe8cb5fcb11b9f | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0udi-0209000000-8d0c8eda18dc8cceda25 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-0udi-0936000000-ead01d21177722db0c04 | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 60V, Negative | splash10-0udi-0942000000-fa589cb74705f9065b0e | Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-03di-0002900001-4dfb6b7d47117fdc7cd5 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0udi-0609200000-9f5f69edfa8bf844814b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0udi-0009100000-8535cabe8cb5fcb11b9f | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0udi-0209000000-8d0c8eda18dc8cceda25 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0udi-0936000000-ead01d21177722db0c04 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0udi-0942000000-fa589cb74705f9065b0e | Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-0udi-0109000000-a98083fb968fef401469 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0119100000-2b8b701588b9f6dc6742 | Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0udi-0119000000-fb6afb6b410e40eaa2f7 | Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0udi-0963000000-49c7b90d9e554b0c30d8 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0uxr-0118900000-27874bbc8fea14f8f47b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0249100000-73f355fdfebc323cb048 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pbi-3942000000-8b4b6457e00c9e67b74a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ik9-1105900000-5e781c8212fbf2748d27 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1139300000-bd6e853b27d25d155e47 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0zfr-5965000000-96e190b31845aefd3093 | Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4478811 |
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ChEMBL ID | CHEMBL402947 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 5320844 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 335 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB37932 |
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CRC / DFC (Dictionary of Food Compounds) ID | HBR39-C:KWD91-S |
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EAFUS ID | Not Available |
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Dr. Duke ID | SPIRAEOSIDE|QUERCETIN-4-O-BETA-D-GLUCOSIDE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00005387 |
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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 | Spiraeoside |
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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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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 | 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 | quinone-reductase inducer | | | DUKE | anti neoplastic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | CHEBI |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — 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.
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