Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:56 UTC |
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Update date | 2019-11-26 03:09:08 UTC |
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Primary ID | FDB013828 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Retinol |
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Description | Constituent of many fish-liver oils, milk, egg-yolk, etc. Nutrient, dietary supplement [DFC]
Retinol is one of the animal forms of vitamin A. It is a diterpenoid and an alcohol. It is convertible to other forms of vitamin A, and the retinyl ester derivative of the alcohol serves as the storage form of the vitamin in animals. [Wikipedia]. Retinol is found in many foods, some of which are beer, common wheat, scrapple, and catfish. |
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CAS Number | 68-26-8 |
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Structure | |
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Synonyms | Synonym | Source |
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(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol | ChEBI | (9cis)-Retinol | ChEBI | 9-cis Retinol | HMDB | (2e,4e,6e,8e)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol | ChEBI | (all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol | HMDB | Afaxin | db_source | Agiolan | biospider | Agoncal | biospider | all-trans-Retinol | manual | all-trans-Retinyl alcohol | biospider | all-trans-Vitamin A | biospider | all-trans-Vitamin A alcohol | biospider | all-trans-Vitamin A1 | biospider | Alphalin | ChEBI | Alphasterol | biospider | Antixerophthalmic vitamin | biospider | Avibon | biospider | Avitol | biospider | Axerol | db_source | Axerophthol | db_source | b-Retinol | biospider | beta-Retinol | biospider | Biosterol | biospider | Epiteliol | biospider | Gadol | db_source | Ophthalamin | biospider | Prepalin | db_source | Retrovitamin a | biospider | Sehkraft a | biospider | trans-Retinol | biospider | trans-Vitamin A alcohol | biospider | Vitamin A | db_source | Vitamin A alcohol | db_source | Vitamin a1 | ChEBI |
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Predicted Properties | |
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Chemical Formula | C20H30O |
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IUPAC name | (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol |
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InChI Identifier | InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8-,17-13+ |
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InChI Key | FPIPGXGPPPQFEQ-MKOSUFFBSA-N |
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Isomeric SMILES | C\C(=C/CO)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C |
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Average Molecular Weight | 286.4516 |
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Monoisotopic Molecular Weight | 286.229665582 |
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Classification |
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Description | Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Retinoids |
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Direct Parent | Retinoids |
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Alternative Parents | |
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Substituents | - Retinoid skeleton
- Diterpenoid
- Fatty alcohol
- Fatty acyl
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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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 83.86%; H 10.56%; O 5.59% | DFC |
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Melting Point | Mp 63-64° | DFC |
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Boiling Point | Bp0.000001 137-138° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 5.68 | BIOBYTE (1995) |
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Experimental pKa | Not Available | |
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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 | [neutral] lmax 328 (E1%/1cm 1780) (EtOH) (Berdy) | 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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Predicted GC-MS | (13Z)-Retinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-1190000000-346a3e44c44d46353e80 | Spectrum | Predicted GC-MS | (13Z)-Retinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-7139000000-7242603c3f7f12c824cd | Spectrum | Predicted GC-MS | (13Z)-Retinol, 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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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-0490000000-97ed49d705440e4d32e7 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00ks-3930000000-7c5bfbd8b838b97dc2aa | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fri-9820000000-6a49bab0c891ffe1e5b2 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-d0ff1cdc72141d0daa0e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-0090000000-c0a067ff8ed271b80945 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ku-4590000000-cfc35aba420e707075f7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-fe93459d3069e264b77f | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05mx-0190000000-f81760535f6050971f92 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00li-0960000000-4dbc516b202b90a6c265 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-015i-1890000000-fb68e645ac6c84dc722c | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05a9-2910000000-aa07b89a9cfe132b8725 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-06dl-5900000000-6de72efc591b252620c9 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 393012 |
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ChEMBL ID | CHEMBL986 |
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KEGG Compound ID | C17276 |
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Pubchem Compound ID | 445354 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17336 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00162 |
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HMDB ID | HMDB00305 |
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CRC / DFC (Dictionary of Food Compounds) ID | JHQ00-R:JHQ00-R |
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EAFUS ID | 3860 |
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Dr. Duke ID | VITAMIN-A|VIT-A |
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BIGG ID | 35081 |
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KNApSAcK ID | C00031437 |
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HET ID | RTL |
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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 | Retinol |
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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 | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Diacylglycerol O-acyltransferase 1 | DGAT1 | O75907 | Diacylglycerol O-acyltransferase 2 | DGAT2 | Q96PD7 | Lecithin retinol acyltransferase | LRAT | O95237 | Acyl-CoA wax alcohol acyltransferase 2 | AWAT2 | Q6E213 | Acyl-CoA wax alcohol acyltransferase 1 | AWAT1 | Q58HT5 | Retinol dehydrogenase 8 | RDH8 | Q9NYR8 | Retinol dehydrogenase 11 | RDH11 | Q8TC12 | Retinol dehydrogenase 10 | RDH10 | Q8IZV5 | Short-chain dehydrogenase/reductase 3 | DHRS3 | O75911 |
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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). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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