Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:41 UTC |
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Update date | 2019-11-26 02:55:16 UTC |
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Primary ID | FDB000709 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (R)-Synephrine |
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Description | (R)-Synephrine belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position (R)-Synephrine is a very strong basic compound (based on its pKa) (R)-Synephrine has been detected, but not quantified in, several different foods, such as citrus, fruits, lemons, mandarin orange (clementine, tangerine), and sweet oranges. This could make (R)-synephrine a potential biomarker for the consumption of these foods. |
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CAS Number | 94-07-5 |
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Structure | |
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Synonyms | Synonym | Source |
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(+)-[(Methylamino)methyl]-benzenemethano | HMDB | (+)-P-Synephrine | HMDB | (+)-Synephrine | HMDB | (+/-)-synephrine | ChEBI | 1-(4-Hydroxyphenyl)-2-(methylamino)ethanol | ChEBI | 1-(4-Hydroxyphenyl)-2-methylaminoethanol | ChEBI | 4-Hydroxy-a-[(methylamino)methyl]benzenemethanol | Generator | 4-Hydroxy-alpha-[(methylamino)methyl]benzenemethanol | ChEBI | 4-Hydroxy-α-[(methylamino)methyl]benzenemethanol | Generator | b-Methylamino-a-(4-hydroxyphenyl)ethyl alcohol | Generator | beta-Methylamino-alpha-(4-hydroxyphenyl)ethyl alcohol | ChEBI | L-Synephrine | manual | Oxedrine | ChEBI | P-Hydroxy-a-[(methylamino)methyl]benzyl alcohol | Generator | P-Hydroxy-alpha-[(methylamino)methyl]benzyl alcohol | ChEBI | P-Hydroxy-α-[(methylamino)methyl]benzyl alcohol | Generator | p-Synephrine | manual | Parasympatol | HMDB | R-(-)-Synephrine | manual | Simpatol | HMDB | Sympaethamin | HMDB | Sympaethamine | HMDB | Sympatol | ChEBI | Synephrine | biospider | β-methylamino-α-(4-hydroxyphenyl)ethyl alcohol | Generator |
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Predicted Properties | |
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Chemical Formula | C9H13NO3 |
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IUPAC name | 4-[(R)-hydroxy[(methylamino)methoxy]methyl]phenol |
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InChI Identifier | InChI=1S/C9H13NO3/c1-10-6-13-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m1/s1 |
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InChI Key | GBBBJHCSNNEWLH-SECBINFHSA-N |
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Isomeric SMILES | CNCO[C@@H](O)C1=CC=C(O)C=C1 |
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Average Molecular Weight | 183.2044 |
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Monoisotopic Molecular Weight | 183.089543287 |
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Classification |
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Description | Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-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-2-unsubstituted benzenoids |
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Direct Parent | 1-hydroxy-2-unsubstituted benzenoids |
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Alternative Parents | |
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Substituents | - 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Hemiaminal
- Hemiacetal
- Secondary amine
- Secondary aliphatic amine
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Aromatic alcohol
- Organooxygen compound
- Organonitrogen compound
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 64.65%; H 7.84%; N 8.38%; O 19.14% | DFC |
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Melting Point | Mp 162-164° dec. | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | -0.45 | HANSCH,C ET AL. (1995) |
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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 | [a]25D -55.6 (c, 0.5 in M HCl) | DFC |
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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 | Not Available |
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External Links |
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ChemSpider ID | 6904 |
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ChEMBL ID | CHEMBL33720 |
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KEGG Compound ID | C04548 |
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Pubchem Compound ID | 7172 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 119 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB04826 |
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CRC / DFC (Dictionary of Food Compounds) ID | BZZ90-X:BFT10-L |
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EAFUS ID | Not Available |
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Dr. Duke ID | SYNEPHRINE |
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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 | Synephrine |
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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 | Descriptor | ID | Definition | Reference |
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cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | cardiovascular | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | hypertensive | | | DUKE | oxytocic | 36063 | A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients). | DUKE | vasoconstrictor | 50514 | Drug used to cause constriction of the blood vessels. | DUKE |
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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 | 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 | — 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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