Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:37 UTC |
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Update date | 2020-09-17 15:41:38 UTC |
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Primary ID | FDB000574 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Pyridoxine |
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Description | Pyridoxine, also known as pyridoxol or vitamin B6, belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. Pyridoxine is a very strong basic compound (based on its pKa). Pyridoxine exists in all living species, ranging from bacteria to humans. Within humans, pyridoxine participates in a number of enzymatic reactions. In particular, pyridoxine can be converted into pyridoxal; which is catalyzed by the enzyme pyridoxine-5'-phosphate oxidase. In addition, pyridoxine can be converted into pyridoxine 5'-phosphate through its interaction with the enzyme pyridoxal kinase. In humans, pyridoxine is involved in vitamin B6 metabolism. Outside of the human body, Pyridoxine is found, on average, in the highest concentration within a few different foods, such as common sages, tarragons, and summer savories and in a lower concentration in hushpuppies, alaska pollocks, and clupeinae (herring, sardine, sprat). Pyridoxine has also been detected, but not quantified in, several different foods, such as ucuhuba, pikeperchs, whiskies, fruit gums, and ginsengs. This could make pyridoxine a potential biomarker for the consumption of these foods. Pyridoxine is a potentially toxic compound. |
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CAS Number | 65-23-6 |
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Structure | |
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Synonyms | Synonym | Source |
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2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridine | ChEBI | 3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine | ChEBI | 3-Hydroxy-4,5-dimethylol-alpha-picoline | ChEBI | 5-Hydroxy-6-methyl-3,4-pyridinedimethanol | ChEBI | Pyridoxol | ChEBI | Vitamin b6 | ChEBI | 3-Hydroxy-4,5-dimethylol-a-picoline | Generator | 3-Hydroxy-4,5-dimethylol-α-picoline | Generator | 2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine | HMDB | 2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine | HMDB | 2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine | HMDB | 3-Hydroxy-2-picoline-4,5-dimethanol | HMDB | Adermine | HMDB | Gravidox | HMDB | Hydoxin | HMDB | Piridossina | HMDB | Piridoxina | HMDB | Pyridoxin | HMDB | Pyridoxinum | HMDB | Pyridoxolum | HMDB | Pyridoxol hydrochloride | HMDB | Rodex | HMDB | Pyridoxine hydrochloride | HMDB | 2-methyl-3-hydroxy-4,5-dihydroxymethylpyridine | biospider | 2-methyl-4,5-dimethylol-pyridin-3-ol | biospider | 2-Picoline-4,5-dimethanol, 3-hydroxy- | biospider | 3-hydroxy-2-Picoline-4,5-dimethanol | biospider | 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- | biospider | 4,5-Bis(hydroxymethyl)-2-methyl-3-pyridinol | biospider | 4,5-bis(hydroxymethyl)-2-methylpyridine-3-ol | biospider | 5-Hydroxy-6-methyl-3,4-pyridinedimethanol, 9CI | db_source | Aderoxine | biospider | Bezatin | biospider | Hexabetalin | biospider | Hexabion | biospider | Pirivitol | biospider | Pridoxine | biospider | Vitamin B6 | manual | Vitamin B6, 8CI | db_source |
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Predicted Properties | |
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Chemical Formula | C8H11NO3 |
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IUPAC name | 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol |
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InChI Identifier | InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3 |
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InChI Key | LXNHXLLTXMVWPM-UHFFFAOYSA-N |
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Isomeric SMILES | CC1=C(O)C(CO)=C(CO)C=N1 |
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Average Molecular Weight | 169.1778 |
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Monoisotopic Molecular Weight | 169.073893223 |
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Classification |
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Description | Belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Pyridoxines |
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Direct Parent | Pyridoxines |
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Alternative Parents | |
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Substituents | - Pyridoxine
- Methylpyridine
- Hydroxypyridine
- Heteroaromatic compound
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Aromatic alcohol
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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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Role | Industrial application: |
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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 | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 56.80%; H 6.55%; N 8.28%; O 28.37% | DFC |
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Melting Point | Mp 160° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | -0.77 | SANGSTER (1993) |
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Experimental pKa | pKa2 8.96 (25°, 0.15M NaCl) | DFC |
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Isoelectric point | Not Available | |
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Charge | 0 | |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-1003-6900000000-1237eaf82dfadfd54d4b | Spectrum | GC-MS | Pyridoxine, 3 TMS, GC-MS Spectrum | splash10-000t-0940000000-30b4702623a6d8fcb4bb | Spectrum | GC-MS | Pyridoxine, non-derivatized, GC-MS Spectrum | splash10-001j-0690000000-0581e2b42fa48c1ea498 | Spectrum | GC-MS | Pyridoxine, 3 TMS, GC-MS Spectrum | splash10-00di-9330000000-32929ff06762b9f5887f | Spectrum | GC-MS | Pyridoxine, 3 TMS, GC-MS Spectrum | splash10-001i-0490000000-34a09ddbbb462aeb02a6 | Spectrum | GC-MS | Pyridoxine, non-derivatized, GC-MS Spectrum | splash10-0f6x-9400000000-486db54a30b61c2eb9d4 | Spectrum | GC-MS | Pyridoxine, non-derivatized, GC-MS Spectrum | splash10-000t-0940000000-30b4702623a6d8fcb4bb | Spectrum | GC-MS | Pyridoxine, non-derivatized, GC-MS Spectrum | splash10-001j-0690000000-0581e2b42fa48c1ea498 | Spectrum | GC-MS | Pyridoxine, non-derivatized, GC-MS Spectrum | splash10-00di-9330000000-32929ff06762b9f5887f | Spectrum | GC-MS | Pyridoxine, non-derivatized, GC-MS Spectrum | splash10-001i-0490000000-34a09ddbbb462aeb02a6 | Spectrum | GC-MS | Pyridoxine, non-derivatized, GC-MS Spectrum | splash10-001j-0790000000-6f8f6e679e03f9119a65 | Spectrum | Predicted GC-MS | Pyridoxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f79-0900000000-0f727b3e23c2481951e8 | Spectrum | Predicted GC-MS | Pyridoxine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-7079000000-2f143e187cb8c078f936 | Spectrum | Predicted GC-MS | Pyridoxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Pyridoxine, TBDMS_2_2, 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 - Quattro_QQQ 10V, Positive (Annotated) | splash10-0vi0-0900000000-bd0de86c072765a5caad | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001i-3900000000-2018b406a3c75213b733 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0059-9200000000-e69bb531deb2a103a476 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0f6x-9400000000-77c43a946c4ae1abf3b9 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-479d4492cc8d634fa366 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0udi-0900000000-486d6a4e5e1a731b7c54 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-05fr-0900000000-4ef09ce9c04561a1085e | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0ab9-1900000000-3298adf6db36689d5d43 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a6r-7900000000-6711954ee96f08344434 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-00di-0900000000-234e90d43a7febd7a098 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0udi-0900000000-137080765c0035b45258 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-001i-0900000000-882ee900a8bba08e2c7c | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-003r-8900000000-e0e11797b63cea991d81 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0059-9100000000-c25384179219411af02c | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0ue9-0900000000-c0e149ce890192397b7f | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0v4i-0900000000-f9f378af3d47ab006806 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-479d4492cc8d634fa366 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0udi-0900000000-486d6a4e5e1a731b7c54 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-05fr-0900000000-4ef09ce9c04561a1085e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0uk9-0900000000-eab5b3411261744df750 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue9-0900000000-cc4dc8719602182ef1eb | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-5900000000-1c2637733578fcdd7c6a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-e89cc69d8b21012ff982 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-059i-0900000000-0ad8d09e042015cb2e33 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9500000000-577a3d87899ca47d539f | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 1025 |
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ChEMBL ID | CHEMBL1364 |
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KEGG Compound ID | C00314 |
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Pubchem Compound ID | 1054 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16709 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00165 |
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HMDB ID | HMDB00239 |
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CRC / DFC (Dictionary of Food Compounds) ID | BDV40-Q:BDV40-Q |
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EAFUS ID | 3262 |
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Dr. Duke ID | VITAMIN-B-6|VIT-B-6|PYRIDOXINE |
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BIGG ID | 34590 |
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KNApSAcK ID | Not Available |
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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 | Pyridoxine |
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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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Phosphoserine aminotransferase | PSAT1 | Q9Y617 |
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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 | 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 | — 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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