4319-02-2

Basic information

• Product Name: 3,5-DIHYDROXY-4-METHOXYBENZOIC ACID
• Synonyms: Benzoic acid, 3,5-dihydroxy-4-methoxy-;HYDROXYISOVANILLIC ACID,5-;3,5-DIHYDROXYANISIC ACID;3,5-DIHYDROXY-4-METHOXYBENZOIC ACID;4-O-METHYL GALLIC ACID;4-METHOXY-3,5-DIHYDROXYBENZOIC ACID;5-HYDROXYISOVANILLIC ACID;3,5-dihydroxy-p-anisic acid
• CAS NO: 4319-02-2
• Molecular Formula: C₈H₈O₅
• Molecular Weight: 184.15
• EINECS: 224-346-9
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 4319-02-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 245 °C
• Boiling Point: 423.4°C at 760 mmHg
• Flash Point: 179.1°C
• Appearance: /
• Density: 1.499g/cm³
• Vapor Pressure: 6.35E-08mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.23±0.10(Predicted)
• CAS DataBase Reference: 3,5-DIHYDROXY-4-METHOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIHYDROXY-4-METHOXYBENZOIC ACID(4319-02-2)
• EPA Substance Registry System: 3,5-DIHYDROXY-4-METHOXYBENZOIC ACID(4319-02-2)

Safety Data

• Hazardous Substances Data: 4319-02-2(Hazardous Substances Data)

Usage

Uses

3,5-Dihydroxy-4-methoxybenzoic Acid is a useful building block in organic synthesis.

InChI:InChI=1/C8H8O5/c1-13-7-5(9)2-4(8(11)12)3-6(7)10/h2-3,9-10H,1H3,(H,11,12)

Upstream product

• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 13089-97-9 methyl 3,5-diacetoxy-4-methoxy benzoate 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 57133-16-1 4,6-Dihydroxy-5,5-dimethoxy-cyclohexa-3,6-diene-1,2,3-tricarboxylic acid trimethyl ester 
• 4073-35-2 3,5-dibromo-4-methoxybenzoic acid 
• 99-24-1 methyl galloate 
• 16534-12-6 3,5-dihydroxy-4-bromobenzoic acid 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 

Downstream Products

• 871875-95-5 4-methoxy-3,5-bis-methoxycarbonyloxy-benzoic acid 
• 773057-00-4 5-(5-cyclohexylamino-[1,3,4]thiadiazol-2-yl)-2-methoxy-benzene-1,3-diol 
• 29865-85-8 3,5-dihydroxy-4-methoxybenzaldehyde 
• 856077-01-5 4-methoxy-3,5-bis-methoxycarbonyloxy-benzoyl chloride 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 

Relevant articles and documents

Synthesis and cytotoxic activities of hexyl-esters derivatives of gallic acid against MCF-7 cell line

Gallic acid is found in many plants, fruits, and foods where the anti-cancer activity is found. However, gallic acid has a problem on the high polarity and low bio availability. So, it takes molecular modifications in order to increase its lipophilicity, which is expected to increase bio availability and cytotoxic activity of gallic acid. Hexyl esters derivatives of gallic acid were synthesized and characterized by spectrometer 1H-NMR, 13C-NMR, mass spectrometry and infrared spectrophotometer (FTIR). All compounds were then evaluated for cytotoxic activity on MCF-7 cell line using MTT method. Compound cis-2′-hexenyl-3,4,5-trimethoxygallate (19) had the lowest IC50 value compared with gallic acid and other derivatives hexyl esters. IC50 value of cis-2′-hexenyl-3,4,5-trimethoxygallate (19) is 14.48 μg/ml. Compound (19) also has approached with IC50 values of gossypol as a positive control. Compound (19) is a potential compound to inhibit growth of MCF-7 cell line.

A concise synthesis of (±)-7-O-galloyltricetiflavan

(±)-7-O-galloyltricetiflavan (1a) was synthesized successfully in five steps from the commercially available trihydroxyacetophenone (2) and trimethoxybenzoyl chloride (3). The flavone 4a was prepared in a one-pot reaction and it gave hex-O-methylflavan 6 followed by acylation and reduction. However, the demethylation of flavan 6, 5-O-acetylflavan 10 and 5-O-phenylacetylflavan 11 by BBr3 gave all the hydrolyzed fragments 7 and 8 as the major products. By contrast, in the same condition, hept-O-methylflavan 9 could provide the desired product (±)-7-O-galloyltricetiflavan (1a) in 91% yield. The additional 5-O-B-Br2 complex may stabilize the ester bond during the demethylation process.

Process for preparing pyrogallol

Pyrogallol is prepared by (A) reacting a halo compound of formula STR1 where X represents Br or I, R1 represents hydrogen, secondary or tertiary alkyl of up to 10 carbon atoms, carboxy or alkoxycarbonyl of 2-5 carbon atoms and R2 represents hydrogen or alkyl of 1-4 carbon atoms, with an alkali metal alkoxide of formula ROM where M represents an alkali metal and R represents alkyl of 1-4 carbon atoms, to replace each X by OR, and then (B) dealkylating each OR and each OR2 where R2 represents alkyl of 1-4 carbon atoms and removing the R1 group where this is not hydrogen.