Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:01 UTC |
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Update date | 2020-09-17 15:38:30 UTC |
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Primary ID | FDB012160 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Riboflavine |
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Description | Riboflavin, also known as lactoflavin or vitamin B2, belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide. Riboflavin is a drug which is used for the treatment of ariboflavinosis (vitamin b2 deficiency). The antioxidant activity of riboflavin is principally derived from its role as a precursor of FAD and the role of this cofactor in the production of the antioxidant reduced glutathione. Riboflavin is an extremely weak basic (essentially neutral) compound (based on its pKa). Riboflavin exists in all living species, ranging from bacteria to humans. Binds to riboflavin hydrogenase, riboflavin kinase, and riboflavin synthase. In humans, riboflavin is involved in the metabolic disorder called the medium chain acyl-coa dehydrogenase deficiency (mcad) pathway. Outside of the human body, Riboflavin is found, on average, in the highest concentration within a few different foods, such as saffrons, saskatoon berries, and leavening agents and in a lower concentration in grape wines, hippoglossus (common halibut), and spiny lobsters. Riboflavin has also been detected, but not quantified in, several different foods, such as bog bilberries, lowbush blueberries, greenthread tea, nanking cherries, and black radish. This could make riboflavin a potential biomarker for the consumption of these foods. Riboflavin is a potentially toxic compound. Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast. |
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CAS Number | 83-88-5 |
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Structure | |
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Synonyms | Synonym | Source |
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1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol | ChEBI | 6,7-Dimethyl-9-D-ribitylisoalloxazine | ChEBI | 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione | ChEBI | 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine | ChEBI | 7,8-Dimethyl-10-ribitylisoalloxazine | ChEBI | e101 | ChEBI | Lactoflavin | ChEBI | Riboflavina | ChEBI | RIBOFLAVINE | ChEBI | Riboflavinum | ChEBI | Vitamin b2 | ChEBI | Vitamin g | ChEBI | Bisulase | Kegg | (-)-Riboflavin | HMDB | 1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol | HMDB | 6,7-Dimethyl-9-ribitylisoalloxazine | HMDB | 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dione | HMDB | Beflavin | HMDB | Beflavine | HMDB | Benzo[g]pteridine riboflavin deriv. | HMDB | e 101 | HMDB | Flavaxin | HMDB | Flavin BB | HMDB | Flaxain | HMDB | FOOD Yellow 15 | HMDB | Hyre | HMDB | Lactobene | HMDB | Lactoflavine | HMDB | Ribipca | HMDB | Ribocrisina | HMDB | Riboderm | HMDB | Ribosyn | HMDB | Ribotone | HMDB | Ribovel | HMDB | Russupteridine yellow III | HMDB | San yellow b | HMDB | Vitaflavine | HMDB | Vitasan b2 | HMDB | Vitamin b 2 | HMDB | 1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol, 9CI | db_source | E101 | db_source | Food Yellow 15 | biospider | Isoalloxazine, 7,8-dimethyl-10-D-ribityl- | biospider | Ovoflavine | db_source | Riboflavin | biospider | Vitamin B2 | db_source | Vitamin G | db_source |
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Predicted Properties | |
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Chemical Formula | C17H20N4O6 |
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IUPAC name | 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione |
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InChI Identifier | InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1 |
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InChI Key | AUNGANRZJHBGPY-SCRDCRAPSA-N |
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Isomeric SMILES | CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1 |
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Average Molecular Weight | 376.3639 |
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Monoisotopic Molecular Weight | 376.138284392 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pteridines and derivatives |
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Sub Class | Alloxazines and isoalloxazines |
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Direct Parent | Flavins |
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Alternative Parents | |
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Substituents | - Flavin
- Diazanaphthalene
- Quinoxaline
- Pyrimidone
- Pyrazine
- Pyrimidine
- Benzenoid
- Heteroaromatic compound
- Vinylogous amide
- Secondary alcohol
- Lactam
- Polyol
- Azacycle
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen 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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 54.25%; H 5.36%; N 14.89%; O 25.51% | DFC |
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Melting Point | Mp 280° dec. | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.0847 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | -1.46 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa2 10.2 (25°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D -125 (20N NaOH) | DFC |
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Spectroscopic UV Data | 455 () (H2O) | DFC |
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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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GC-MS | Riboflavine, non-derivatized, GC-MS Spectrum | splash10-006x-4980000000-dd278a577316361d270a | Spectrum | GC-MS | Riboflavine, non-derivatized, GC-MS Spectrum | splash10-006x-4980000000-dd278a577316361d270a | Spectrum | Predicted GC-MS | Riboflavine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0btc-9014000000-75f046dc3c6cb008690e | Spectrum | Predicted GC-MS | Riboflavine, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0zfs-5146149000-f9db57dd1ccd4a014604 | Spectrum | Predicted GC-MS | Riboflavine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Riboflavine, TMS_3_5, 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 (UPLC Q-Tof Premier, Waters) , Negative | splash10-0a4i-0091000000-a82c54d3153103fcdb1f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-0091000000-a82c54d3153103fcdb1f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0a4i-0090000000-2aff124ee1fc62c13844 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0a4i-0090000000-f8b29c3e2c601a944a6c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a94 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0090000000-5288e9226616bb75603c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0093000000-5999e10d04a53f4dae9b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0091000000-8f391045e25f26d53384 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-08fv-0290000000-b4d5f66b726c01d08c55 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-4690000000-d195fd5aee22ece7f2ec | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0039000000-549fbc0a59262f64680e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0195000000-58354696aaddaffc0fd8 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0f76-9231000000-67715e21d6e9ce2655fe | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0a4i-0090000000-838afb0228d293bee0a3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-2190000000-b659be001c9aa265c257 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0a4i-0090000000-21473bfb7f4a3eafd059 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0019000000-86365dedafa031aa7787 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-4390000000-ac1b59ab7cc2209f4241 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00dj-4900000000-72d33eb27b9bd6a13d9e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-004l-0569000000-874b71fdc78d04853bf0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-004i-0239000000-659ca9fae9643f3ce73d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004l-0569000000-874b71fdc78d04853bf0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0006-0092000000-1f1be5508c1d50d8dff7 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0006-0092000000-74bf0b86efe72fe37198 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-057i-0069000000-bb0522be4472e049dbc5 | 2017-09-14 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 431981 |
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ChEMBL ID | CHEMBL1534 |
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KEGG Compound ID | C00255 |
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Pubchem Compound ID | 493570 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17015 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00140 |
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HMDB ID | HMDB00244 |
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CRC / DFC (Dictionary of Food Compounds) ID | HDV43-H:HDV43-H |
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EAFUS ID | 3302 |
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Dr. Duke ID | VITAMIN-B-2|VIT-B2|RIBOFLAVIN |
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BIGG ID | 34409 |
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KNApSAcK ID | Not Available |
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HET ID | RBF |
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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 | Riboflavin |
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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 | |
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Enzymes | Name | Gene Name | UniProt ID |
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Lysosomal acid phosphatase | ACP2 | P11117 | Testicular acid phosphatase | ACPT | Q9BZG2 | Prostatic acid phosphatase | ACPP | P15309 | Lysophosphatidic acid phosphatase type 6 | ACP6 | Q9NPH0 | Putative uncharacterized protein ACP1 | ACP1 | B5MCC7 | Glycogen phosphorylase, liver form | PYGL | P06737 | Solute carrier family 52, riboflavin transporter, member 1 | SLC52A1 | Q9NWF4 |
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Pathways | |
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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 | show |
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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 | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — 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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