Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-25 23:33:16 UTC |
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Update Date | 2016-11-09 01:18:24 UTC |
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Accession Number | CHEM027183 |
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Identification |
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Common Name | (13Z)-Retinol |
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Class | Small Molecule |
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Description | |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(13cis)-Retinol | ChEBI | (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol | ChEBI | RETINOL | ChEBI | Neovitamin a | Kegg | (11-cis,13-cis)-Retinol acetate | HMDB | 11,13-Di-cis-vitamin a acetate | HMDB | 11-cis-13-cis-Retinol acetate | HMDB | 11-cis-13-cis-Retinyl acetate | HMDB |
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Chemical Formula | C20H30O |
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Average Molecular Mass | 286.452 g/mol |
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Monoisotopic Mass | 286.230 g/mol |
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CAS Registry Number | 2052-63-3 |
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IUPAC Name | (2Z,4E,6E,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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Traditional Name | 13-cis retinol |
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SMILES | C\C(=C/CO)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C |
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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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Chemical Taxonomy |
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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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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-1190000000-346a3e44c44d46353e80 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0006-7139000000-7242603c3f7f12c824cd | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0290000000-25c523b646154b291da8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-05gj-3900000000-a63c286f931608f650a3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-05mo-9700000000-e627db30469c74bb037f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-1490000000-7205fba02aeb80622df8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00m0-3920000000-951836eaf171751b137c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0lei-9810000000-b9b76a3e956e61a7d39e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-575d71f5f53354f828c2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-0090000000-c71c47589510cf7c1a0b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ku-3690000000-26f7587a1f34c10cd8f7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-fe93459d3069e264b77f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05mx-0190000000-f81760535f6050971f92 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00li-0960000000-4dbc516b202b90a6c265 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-015i-1890000000-fb68e645ac6c84dc722c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05a9-2910000000-aa07b89a9cfe132b8725 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-06dl-5900000000-6de72efc591b252620c9 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-052r-2950000000-c24ec8ff8d0ba6c1f23f | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0006221 |
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FooDB ID | FDB112229 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | 2455099 |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Vitamin A |
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Chemspider ID | 8079655 |
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ChEBI ID | 45479 |
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PubChem Compound ID | 9904001 |
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Kegg Compound ID | C19962 |
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YMDB ID | Not Available |
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ECMDB ID | ECMDB21660 |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Albert, Klaus; Schlotterbeck, Goetz; Braumann, Ulrich; Haendel, Heidrun; Spraul, Manfred; Krack, Gerhard. Structure determination of vitamin A acetate isomers through coupled HPLC and 1H NMR spectroscopy. Angewandte Chemie, International Edition in English (1995), 34(9), 1014-16. | 2. Driessen CA, Winkens HJ, Hoffmann K, Kuhlmann LD, Janssen BP, Van Vugt AH, Van Hooser JP, Wieringa BE, Deutman AF, Palczewski K, Ruether K, Janssen JJ: Disruption of the 11-cis-retinol dehydrogenase gene leads to accumulation of cis-retinols and cis-retinyl esters. Mol Cell Biol. 2000 Jun;20(12):4275-87. |
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