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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB120374 |
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Identification |
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| Name: |
3-methoxy-4-hydroxyphenylglycolaldehyde |
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| Description: | 3-Methoxy-4-hydroxyphenylglycolaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of metanephrine. Metanephrine is an O-methylated metabolite formed by catechol-O-methyltransferase (COMT) from epinephrine. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. The inhibitory effects of methoxy phenolic derivatives on epinephrine-induced platelet aggregation may possibly be attributed to their free radical scavenging properties. There is substantial evidence to conclude that an internal rapid autoregulation of epinephrine-induced platelet aggregation, caused by its metabolic degradation products, takes place in vivo. (PMID: 11958479 , 9706478 ). |
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Structure |
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| Synonyms: | - MOPEGAL
- 4-hydroxy-3-methoxymandelaldehyde
- 3-methoxy 4-hydroxy mandelic aldehyde
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Chemical Formula: |
C9H10O4 |
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| Average Molecular Weight: |
182.176 |
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| Monoisotopic Molecular
Weight: |
182.0579 |
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| InChI Key: |
VISAJVAPYPFKCL-QMMMGPOBSA-N |
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| InChI: | InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3/t8-/m0/s1 |
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| CAS
number: |
17592-23-3 |
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| IUPAC Name: | 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde |
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Traditional IUPAC Name: |
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde |
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| SMILES: | COC1(=C(O)C=CC(C(O)C=O)=C1) |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
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Kingdom |
Chemical entities |
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| Super Class | Organic compounds |
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Class |
Benzenoids |
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| Sub Class | Phenols |
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Direct Parent |
Methoxyphenols |
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| Alternative Parents |
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| Substituents |
- Methoxyphenol
- Phenylacetaldehyde
- Anisole
- Phenoxy compound
- Phenol ether
- Methoxybenzene
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Monocyclic benzene moiety
- Alpha-hydroxyaldehyde
- Secondary alcohol
- Ether
- Aromatic alcohol
- Organooxygen compound
- Aldehyde
- Carbonyl group
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic homomonocyclic compound
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| Molecular Framework |
Aromatic homomonocyclic compounds |
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| External Descriptors |
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Physical Properties |
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| State: |
Solid |
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| Charge: | 0 |
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Melting point: |
Not Available |
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| Experimental Properties: |
| Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | 0.517 | Not Available |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Not Available |
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| Reactions: | |
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Pathways: |
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Spectra |
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| Spectra: |
Not Available |
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References |
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| References: |
- Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Fujisawa S, Sato S: Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia. Auton Neurosci. 2002 Mar 18;96(2):131-9. [11958479 ]
- Evangelou AM, Malamas MP, Vezyraki P, Karkabounas SC: Is epinephrine-induced platelet aggregation autoregulated by its metabolic degradation products in vivo? In Vivo. 1998 May-Jun;12(3):321-5. [9706478 ]
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
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