Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:07:25 UTC |
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Update date | 2020-02-24 19:10:47 UTC |
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Primary ID | FDB007049 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Cyanidin 3-rutinoside |
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Description | Cyanidin 3-rutinoside, also known as keracyanin, belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Thus, cyanidin 3-rutinoside is considered to be a flavonoid. Cyanidin 3-rutinoside is found, on average, in the highest concentration within a few different foods, such as blackberries (Rubus), andean blackberries (Rubus glaucus), and sweet cherries (Prunus avium) and in a lower concentration in sour cherries (Prunus cerasus), olives (Olea europaea), and blackcurrants (Ribes nigrum). Cyanidin 3-rutinoside has also been detected, but not quantified in, several different foods, such as lowbush blueberries (Vaccinium angustifolium), highbush blueberries (Vaccinium corymbosum), summer grapes (Vitis aestivalis), wheats (Triticum), and common grapes (Vitis vinifera). This could make cyanidin 3-rutinoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyanidin 3-rutinoside. |
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CAS Number | 28338-59-2 |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C27H31O15 |
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IUPAC name | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium |
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InChI Identifier | InChI=1S/C27H30O15/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31)/p+1/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+/m0/s1 |
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InChI Key | USNPULRDBDVJAO-FXCAAIILSA-O |
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Isomeric SMILES | [H][C@@]1(C)O[C@@]([H])(OC[C@@]2([H])O[C@@]([H])(OC3=CC4=C(C=C(O)C=C4O)[O+]=C3C3=CC(O)=C(O)C=C3)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O |
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Average Molecular Weight | 595.526 |
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Monoisotopic Molecular Weight | 595.166295322 |
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Classification |
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Description | Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a 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 | Anthocyanidin-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Anthocyanidin-3-o-glycoside
- Flavonoid-3-o-glycoside
- Hydroxyflavonoid
- 7-hydroxyflavonoid
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Anthocyanidin
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- Catechol
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Monocyclic benzene moiety
- Oxane
- Benzenoid
- Heteroaromatic compound
- Secondary alcohol
- Polyol
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Organic oxygen compound
- Hydrocarbon derivative
- Alcohol
- Organooxygen compound
- Organic cation
- 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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Physico-Chemical Properties |
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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 | Not Available | |
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Melting Point | Not Available | |
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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 | Not Available | |
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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 | Cyanidin 3-rutinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00pi-7290080000-4e9e17157d81edbbc7b2 | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00kk-7270009000-a677df67be0186eddbe9 | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, "Cyanidin 3-rutinoside,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Cyanidin 3-rutinoside, TMS_2_13, 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 - LC-ESI-QTOF , negative | splash10-000x-0090070000-125bca6d3508badde83f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0090080000-6c6a0d2425f4a8ce2dd0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002u-0690200000-d0f495f57a6a08951ae3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-001r-0090000000-5d9be53d8851211d98b9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000x-0090050000-edf1f099fb6afbd7bdd4 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-001r-0090000000-3fbc8f30a8f68e2b6b12 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0090000000-50fc7a85af67b684d655 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0090030000-6c1cc95884382202267a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0090020000-af027bb2664bb06e30d3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0030090000-cb5228a5a554147643b0 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0000090000-cba1bd53595923c8dc6f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-000i-0090000000-735ac235caa69be3d230 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-000i-0090000000-14f4866fec6873c2487b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0000090000-fd1c98249ab2ecbed87b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0006-0070090000-dd1ac5fab438c8b60489 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0000090000-2f47b76af7994574f89a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-000i-0090000000-3dfd5d4c6dbc9b0428d4 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Negative | splash10-001r-0090000000-91e1340eb79d12ed3d6d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-001r-0090000000-776e76ecfc8c90bd97a9 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0211090000-99bd764f2c2a7dca281e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002g-0711090000-878065c4a8c8fed57e8c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-06rb-6911010000-4f517c2e03a1ff30becf | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-4421090000-61295fb4e486fff583fd | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ow-5911020000-3e796461f98c10c1e95f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0c04-9520000000-9e3f42b0650d9235dca8 | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 390288 |
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ChEMBL ID | CHEMBL505251 |
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KEGG Compound ID | C08620 |
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Pubchem Compound ID | 441674 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16726 |
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Phenol-Explorer ID | 56 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB31458 |
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CRC / DFC (Dictionary of Food Compounds) ID | ODW39-O:BFH51-Q |
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EAFUS ID | Not Available |
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Dr. Duke ID | ANTIRRHININ|ANTIRHININ|CYANIDIN-3-RHAMNOSYLGLUCOSIDE|CYANIDIN-3-RUTINOSIDE|KERACYANIN|SAMBUCINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002376 |
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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 | Cyanidin_3-rutinoside |
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Phenol-Explorer Metabolite ID | 10 |
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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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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 |
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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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