Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:21:12 UTC |
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Update date | 2015-10-09 22:31:29 UTC |
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Primary ID | FDB022891 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Phenylephrine |
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Description | Phenylephrine, also known as mesaton or m-sympathol, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. Phenylephrine is a very strong basic compound (based on its pKa). Phenylephrine is a bitter tasting compound. |
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CAS Number | 59-42-7 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol | ChEBI | Fenilefrina | ChEBI | L-(3-Hydroxyphenyl)-N-methylethanolamine | ChEBI | Phenylephrinum | ChEBI | R(-)-Phenylephrine | ChEBI | Phenylephrine minims | Kegg | (-)-m-Hydroxy-a-(methylaminomethyl)benzyl alcohol | Generator | (-)-m-Hydroxy-α-(methylaminomethyl)benzyl alcohol | Generator | Adrianol | HMDB | Ak-dilate | HMDB | Ak-nefrin | HMDB | Alcon efrin | HMDB | Alconefrin nasal drops 12 | HMDB | Alconefrin nasal drops 25 | HMDB | Alconefrin nasal drops 50 | HMDB | Alconefrin nasal spray 25 | HMDB | Biomydrin | HMDB | Dilatair | HMDB | Dionephrine | HMDB | Doktors | HMDB | Duration | HMDB | I-phrine | HMDB | Isophrim | HMDB | Isophrin | HMDB | Isopto frin | HMDB | m-Methylaminoethanolphenol | HMDB | m-Oxedrine | HMDB | m-Sympathol | HMDB | m-Sympatol | HMDB | m-Synephrine | HMDB | Mesaton | HMDB | Mesatone | HMDB | Mesatonum | HMDB | Metaoxedrin | HMDB | Metaoxedrine | HMDB | Metaoxedrinum | HMDB | Metasympatol | HMDB | Metasynephrine | HMDB | Mezaton | HMDB | Minims phenylephrine | HMDB | Mydfrin | HMDB | Neo-synephrine | HMDB | Neo-synephrine nasal drops | HMDB | Neo-synephrine nasal jelly | HMDB | Neo-synephrine nasal spray | HMDB | Neo-synephrine pediatric nasal drops | HMDB | Neofrin | HMDB | Neophryn | HMDB | Neosynephrine | HMDB | Nostril | HMDB | Nostril spray pump | HMDB | Nostril spray pump mild | HMDB | Ocu-phrin sterile eye drops | HMDB | Ocu-phrin sterile ophthalmic solution | HMDB | Ocugestrin | HMDB | Phenoptic | HMDB | Prefrin | HMDB | Prefrin liquifilm | HMDB | Pyracort D | HMDB | R(-)-Mezaton | HMDB | Relief eye drops for red eyes | HMDB | Rhinall | HMDB | Spersaphrine | HMDB | Vicks sinex | HMDB | Visadron | HMDB | Neo synephrine | HMDB | Phenylephrine tannate | HMDB | Tannate, phenylephrine | HMDB | (R)-3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol | HMDB | Phenylephrine hydrochloride | HMDB | Ak-Dilate | hmdb | Ak-Nefrin | hmdb | Alconefrin Nasal Drops 12 | hmdb | Alconefrin Nasal Drops 25 | hmdb | Alconefrin Nasal Drops 50 | hmdb | Alconefrin Nasal Spray 25 | hmdb | I-Phrine | hmdb | Isopto Frin | hmdb | Minims Phenylephrine | hmdb | Neo-Synephrine | hmdb | Neo-Synephrine Nasal Drops | hmdb | Neo-Synephrine Nasal Jelly | hmdb | Neo-Synephrine Nasal Spray | hmdb | Neo-Synephrine Pediatric Nasal Drops | hmdb | Nostril Spray Pump | hmdb | Nostril Spray Pump Mild | hmdb | Ocu-Phrin Sterile Eye Drops | hmdb | Ocu-Phrin Sterile Ophthalmic Solution | hmdb | Prefrin Liquifilm | hmdb | Relief Eye Drops for Red Eyes | hmdb | Vicks Sinex | hmdb |
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Predicted Properties | |
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Chemical Formula | C9H13NO2 |
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IUPAC name | 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol |
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InChI Identifier | InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1 |
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InChI Key | SONNWYBIRXJNDC-VIFPVBQESA-N |
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Isomeric SMILES | CNC[C@H](O)C1=CC(O)=CC=C1 |
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Average Molecular Weight | 167.205 |
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Monoisotopic Molecular Weight | 167.094628665 |
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Classification |
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Description | Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | 1-hydroxy-4-unsubstituted benzenoids |
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Direct Parent | 1-hydroxy-4-unsubstituted benzenoids |
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Alternative Parents | |
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Substituents | - 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Monocyclic benzene moiety
- 1,2-aminoalcohol
- Secondary alcohol
- Secondary aliphatic amine
- Secondary amine
- Alcohol
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Amine
- Aromatic alcohol
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Role | Industrial application: |
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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 | 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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GC-MS | Phenylephrine, 2 TMS, GC-MS Spectrum | splash10-014i-0900000000-b11a2a880d1683fa6cae | Spectrum | GC-MS | Phenylephrine, 2 TMS, GC-MS Spectrum | splash10-01b9-6900000000-bbdd210a846be116dbcd | Spectrum | GC-MS | Phenylephrine, non-derivatized, GC-MS Spectrum | splash10-014i-0900000000-b11a2a880d1683fa6cae | Spectrum | GC-MS | Phenylephrine, non-derivatized, GC-MS Spectrum | splash10-01b9-6900000000-bbdd210a846be116dbcd | Spectrum | Predicted GC-MS | Phenylephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9200000000-3ea7ffd258ffba5a376a | Spectrum | Predicted GC-MS | Phenylephrine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-4920000000-54a2b2a88914c83610f2 | Spectrum | Predicted GC-MS | Phenylephrine, 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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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-0udi-0900000000-d95a741ffcfe3f7bb7e9 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0006-9800000000-7695881b36499169fb71 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-054o-9200000000-888fce606d860cd39be2 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-edfcbc18ccdb6872b791 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00di-0900000000-15132688bbc7ac0be42f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00di-2900000000-34ccc7192518d4c14210 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-00di-3900000000-e619f4210f81c11f61be | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-00dl-6900000000-3178337a019ac9bf313d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0gb9-0900000000-e738818606836c1d6d1a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0udi-0900000000-36b72327f64f1355a502 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-052o-4900000000-935a9659fe39602b138d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-052f-9800000000-7d83555b537d6fec673b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-054o-9400000000-5ef2f6d1da57087e6ac7 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-014i-0900000000-4a910a2109ba191b96e7 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-edfcbc18ccdb6872b791 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-0900000000-15132688bbc7ac0be42f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-2900000000-34ccc7192518d4c14210 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-3900000000-e8a5a4f1aae0796866a7 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00dl-6900000000-3178337a019ac9bf313d | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0uxr-0900000000-8c4893aa69ea6a1ceecb | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uxr-0900000000-4406afb22d76646e2ef8 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01c3-7900000000-56a2a2741d2166bf31bc | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-0cf5a5fa80f87facb9ad | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014j-2900000000-687762e0d4bf3efbffec | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9400000000-140e96de62b4341791d9 | 2017-07-26 | 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, 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 | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 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 | 5818 |
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ChEMBL ID | CHEMBL1215 |
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KEGG Compound ID | C07441 |
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Pubchem Compound ID | 6041 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00388 |
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HMDB ID | HMDB02182 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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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 | Phenylephrine |
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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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Alpha-2A adrenergic receptor | ADRA2A | P08913 | Alpha-2B adrenergic receptor | ADRA2B | P18089 |
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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 | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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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 | |
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