| Identification | More | [Name]
3,4-DIHYDROXY-5-METHOXYBENZOIC ACID | [CAS]
3934-84-7 | [Synonyms]
3,4-DIHYDROXY-5-METHOXYBENZOIC ACID
3-METHOXY-4,5-DIHYDROXYBENZOIC ACID
3-O-METHYLGALLATE
3-O-METHYL GALLIC ACID
4,5-DIHYDROXY-3-METHOXYBENZOIC ACID
5-HYDROXYVANILLIC ACID
METHYLGALLIC ACID, 3-O-
RARECHEM AL BE 0702
4,5-dihydroxy-m-anisic acid
5-HYDROXYVANILLIC ACID 97%
METHYLGALLIC ACID, 3-O-(RG)
3-METHOXY-4,5-DIHYDROXYBENZOIC ACID 97%
4 5-DIHYDROXY-3-METHOXYBENZOICCID 97% | [EINECS(EC#)]
223-512-8 | [Molecular Formula]
C8H8O5 | [MDL Number]
MFCD00016518 | [Molecular Weight]
184.15 | [MOL File]
3934-84-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
220℃ | [Boiling point ]
433.7±45.0 °C(Predicted) | [density ]
1.499±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated) | [form ]
Solid | [pka]
4.33±0.10(Predicted) | [color ]
Off-White to Pale Brown | [Water Solubility ]
Water: 2.2 mg/mL (11.95 mM) | [InChI]
InChI=1S/C8H8O5/c1-13-6-3-4(8(11)12)2-5(9)7(6)10/h2-3,9-10H,1H3,(H,11,12) | [InChIKey]
KWCCUYSXAYTNKA-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC(OC)=C(O)C(O)=C1 | [LogP]
1.190 (est) | [CAS DataBase Reference]
3934-84-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
WGK 3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Uses]
3-O-Methylgallic acid (3,4-Dihydroxy-5-methoxybenzoic acid) is an anthocyanin metabolite and has potent antioxidant capacity. 3-O-methylgallic acid inhibits Caco-2 cell proliferation with an IC50 value of 24.1 μM. 3-O-methylgallic acid also induces cell apoptosis and has anti-cancer effects[1][2][3]. | [Definition]
ChEBI: A member of the class of benzoic acids that is gallic acid in which the phenolic hydroxy group at position 3 is converted to the corresponding methyl ether. | [References]
[1] Forester SC, et al. Gut metabolites of anthocyanins, gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde, inhibit cell proliferation of Caco-2 cells. J Agric Food Chem. 2010 May 12;58(9):5320-7. DOI:10.1021/jf9040172
[2] Forester SC, The anthocyanin metabolites gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde decrease human colon cancer cell viability by regulating pro-oncogenic signals. Mol Carcinog. 2014 Jun;53(6):432-9. DOI:10.1002/mc.21974
[3] Gargouri OD, et al. Synthesis of 3-O-methylgallic acid a powerful antioxidant by electrochemical conversion of syringic acid. Biochim Biophys Acta. 2013 Jun;1830(6):3643-9. DOI:10.1016/j.bbagen.2013.02.012 |
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