3,4-DIHYDROXY-5-METHOXYBENZOIC ACID Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36/37/39

3,4-DIHYDROXY-5-METHOXYBENZOIC ACID Usage And Synthesis

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

3,4-DIHYDROXY-5-METHOXYBENZOIC ACID(3934-84-7)Related Product Information

• Ellagic acid
• Methyl 2-amino-3,4,5-trimethoxybenzoate
• Methyl 3,4,5-trimethoxybenzoate
• 3,4,5-Trimethoxy benzoic acid
• SYROSINGOPINE
• Ethyl 3,4,5-trimethoxybenzoate
• 3-Hydroxy-4,5-dimethoxybenzoic acid
• Reserpine
• Methyl 2-nitro-3,4,5-trimethoxybenzoate
• 3,4-DIHYDROXY-5-METHOXYBENZOIC ACID
• 3,4,5-TRIETHOXYBENZOIC ACID
• Methyl syringate
• Syringic acid
• 3,5-DIHYDROXY-4-METHOXYBENZOIC ACID
• 3,4-DIHYDROXY-5-METHOXYBENZOIC ACID METHYL ESTER
• 2,3-DIHYDROXY-4-METHOXYBENZOIC ACID,DIHYDROXY-4-METHOXYBENZOIC ACID,2,3-
• 3-Methoxybenzoic acid
• Gallic acid