Meciadanol
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Names
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IUPAC name
3-Methoxyflavan-3′,4′,5,7-tetrol
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Systematic IUPAC name
(2R,3S)-2-(3,4-Dihydroxyphenyl)-3-methoxy-3,4-dihydro-2H-1-benzopyran-5,7-diol
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Other names
3-O-Methylcatechin Meciadanolum 3',4',5,7-Tetrahydroxy-3-methoxyflavan (2R,3S)-2-(3,4-Dihydroxyphenyl)-3-methoxy-5,7-chromandiol
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Identifiers
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ChemSpider
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ECHA InfoCard
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100.059.719
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UNII
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InChI=1S/C16H16O6/c1-21-15-7-10-12(19)5-9(17)6-14(10)22-16(15)8-2-3-11(18)13(20)4-8/h2-6,15-20H,7H2,1H3/t15-,16+/m0/s1 N Key: PDHSAQOQVUXZGQ-JKSUJKDBSA-N N InChI=1/C16H16O6/c1-21-15-7-10-12(19)5-9(17)6-14(10)22-16(15)8-2-3-11(18)13(20)4-8/h2-6,15-20H,7H2,1H3/t15-,16+/m0/s1 Key: PDHSAQOQVUXZGQ-JKSUJKDBBQ
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CO[C@H]1CC2=C(C=C(C=C2O[C@@H]1C3=CC(=C(C=C3)O)O)O)O
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Properties
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C16H16O6
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Molar mass
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304.298 g·mol−1
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Meciadanol is a synthetic O-methylated flavanol. It is the 3-O-methylation of catechin.
It inhibits histidine decarboxylase in rats.[1]
References
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Flavan-3-ols | |
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O-methylated flavan-3ols |
- (3-O-methylcatechin)
- Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
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Glycosides |
- Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside)
- Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside)
- Catechin-3-O-glucoside
- Catechin-3'-O-glucoside
- Catechin-4'-O-glucoside
- Catechin-5-O-glucoside
- Catechin-7-O-glucoside
- (+)-Catechin 7-O-β-D-xylopyranoside
- Epicatechin-3′-O-glucoside
- Glochiflavanoside A, B, C D
- Polydine ((+)-catechin 7-O-α-L-arabinoside)
- Symplocoside (3'-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
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Acetylated | |
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Gallate esters | |
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Misc. | |
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Non-specific | AAADTooltip Aromatic L-amino acid decarboxylase | |
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MAOTooltip Monoamine oxidase | |
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Phenethylamines (dopamine, epinephrine, norepinephrine) | PAHTooltip Phenylalanine hydroxylase | |
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THTooltip Tyrosine hydroxylase | |
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DBHTooltip Dopamine beta-hydroxylase | |
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PNMTTooltip Phenylethanolamine N-methyltransferase |
- Inhibitors: CGS-19281A
- SKF-64139
- SKF-7698
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COMTTooltip Catechol-O-methyl transferase | |
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Tryptamines (serotonin, melatonin) | TPHTooltip Tryptophan hydroxylase | |
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AANATTooltip Serotonin N-acetyl transferase | |
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ASMTTooltip Acetylserotonin O-methyltransferase | |
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Histamine | HDCTooltip Histidine decarboxylase | |
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HNMTTooltip Histamine N-methyltransferase |
- Substrates→Products: Histamine→N-Methylhistamine
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DAOTooltip Diamine oxidase |
- Substrates→Products: Histamine→Imidazole acetic acid
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See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins |