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  • Benzoic acid,3,4,5-trimethoxy-, methyl ester
Name:Benzoic acid,3,4,5-trimethoxy-, methyl ester
CAS No:1916-07-0

PRODUCT DESCRIPTION

【Name】
Benzoic acid,3,4,5-trimethoxy-, methyl ester
【Iupac name】
methyl 3,4,5-trimethoxybenzoate
【CAS Registry number】
1916-07-0
【Synonyms】
3,4,5-Trimethoxybenzoicacid methyl ester
Methyl eudesmate
Methylgallate trimethyl ether
Methyl tri-O-methylgallate
NSC 16955
Trimethylgallicacid methyl ester
【EINECS(EC#)】
217-629-3
【Molecular Formula】
C11H14O5 (Products with the same molecular formula)
【Molecular Weight】
226.23
【Inchi】
InChI=1/C11H14O5/c1-13-8-5-7(11(12)16-4)6-9(14-2)10(8)15-3/h5-6H,1-4H3
【InChIKey】
KACHFMOHOPLTNX-UHFFFAOYSA-N
【Canonical SMILES】
COC1=CC(=CC(=C1OC)OC)C(=O)OC
【MOL File】
1916-07-0.mol

Chemical and Physical Properties

【Appearance】
White to off-white crystalline powder
【Density】
1.134 g/cm3
【Melting Point】
81-85℃
【Boiling Point】
274-275℃
【Vapour】
0.00538mmHg at 25°C
【Refractive Index】
1.494
【Flash Point】
115.2 °C
【Water】
SOLVENT
【Solubilities】
SOLVENT
【Stability】
Stable under normal temperatures and pressures.
【Storage temp】
Store in a cool, dry place. Store in a tightly closed container.
【Computed Properties】
Molecular Weight:226.22586 [g/mol]
Molecular Formula:C11H14O5
XLogP3-AA:1.7
H-Bond Donor:0
H-Bond Acceptor:5
Rotatable Bond Count:5
Exact Mass:226.084124
MonoIsotopic Mass:226.084124
Topological Polar Surface Area:54
Heavy Atom Count:16
Formal Charge:0
Complexity:216
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Ring Count:1
Effective Rotor Count:5
Conformer Sampling RMSD:0.6
CID Conformer Count:13

Safety and Handling

【Hazard Codes】
Xi
【Safety Statements 】
S24/25
【Hazard Note】
Irritant
【Safety】
Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating vapors.
【Transport】
25kgs
【Specification】

The IUPAC name of this chemical is methyl 3,4,5-trimethoxybenzoate. With the CAS registry number 1916-07-0, it is also named as Trimethylgallic acid methyl ester. The product's categories are Aromatic Esters; C10 to C11; Carbonyl Compounds; Esters. It is white to light yellow powder which should be sealed in the container and stored in the cool and dry place. Additionally, people should avoid contact with skin and eyes. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.74; (4)ACD/LogD (pH 7.4): 1.74; (5)ACD/BCF (pH 5.5): 12.29; (6)ACD/BCF (pH 7.4): 12.29; (7)ACD/KOC (pH 5.5): 209.68; (8)ACD/KOC (pH 7.4): 209.68; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.494; (13)Molar Refractivity: 58.06 cm3; (14)Molar Volume: 199.3 cm3; (15)Polarizability: 23.01×10-24 cm3; (16)Surface Tension: 34.2 dyne/cm; (17)Enthalpy of Vaporization: 51.29 kJ/mol; (18)Vapour Pressure: 0.00538 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 226.084124; (21)MonoIsotopic Mass: 226.084124; (22)Topological Polar Surface Area: 54; (23)Heavy Atom Count: 16; (24)Complexity: 216.

Preparation of Methyl 3,4,5-trimethoxybenzoate: It can be obtained by methylation reaction of gallic acid and dimethyl sulfate.

Uses of Methyl 3,4,5-trimethoxybenzoate: It can be used as pharmaceutical intermediate and is also the main raw material of anti-anxiety drugs trimetozine, intestinal medicine trimebutine maleate, etc. In addition, It can react with 4-methoxy-benzaldehyde to get (E)-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enoic acid. This reaction needs reagent Et3N and Ac2O by heating. The reaction time is 12 hours. The yield is 76%.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)c1cc(OC)c(OC)c(OC)c1
2. InChI:InChI=1/C11H14O5/c1-13-8-5-7(11(12)16-4)6-9(14-2)10(8)15-3/h5-6H,1-4H3
  
The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07253,
【Report】

The IUPAC name of this chemical is methyl 3,4,5-trimethoxybenzoate. With the CAS registry number 1916-07-0, it is also named as Trimethylgallic acid methyl ester. The product's categories are Aromatic Esters; C10 to C11; Carbonyl Compounds; Esters. It is white to light yellow powder which should be sealed in the container and stored in the cool and dry place. Additionally, people should avoid contact with skin and eyes. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.74; (4)ACD/LogD (pH 7.4): 1.74; (5)ACD/BCF (pH 5.5): 12.29; (6)ACD/BCF (pH 7.4): 12.29; (7)ACD/KOC (pH 5.5): 209.68; (8)ACD/KOC (pH 7.4): 209.68; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.494; (13)Molar Refractivity: 58.06 cm3; (14)Molar Volume: 199.3 cm3; (15)Polarizability: 23.01×10-24 cm3; (16)Surface Tension: 34.2 dyne/cm; (17)Enthalpy of Vaporization: 51.29 kJ/mol; (18)Vapour Pressure: 0.00538 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 226.084124; (21)MonoIsotopic Mass: 226.084124; (22)Topological Polar Surface Area: 54; (23)Heavy Atom Count: 16; (24)Complexity: 216.

Preparation of Methyl 3,4,5-trimethoxybenzoate: It can be obtained by methylation reaction of gallic acid and dimethyl sulfate.

Uses of Methyl 3,4,5-trimethoxybenzoate: It can be used as pharmaceutical intermediate and is also the main raw material of anti-anxiety drugs trimetozine, intestinal medicine trimebutine maleate, etc. In addition, It can react with 4-methoxy-benzaldehyde to get (E)-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enoic acid. This reaction needs reagent Et3N and Ac2O by heating. The reaction time is 12 hours. The yield is 76%.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)c1cc(OC)c(OC)c(OC)c1
2. InChI:InChI=1/C11H14O5/c1-13-8-5-7(11(12)16-4)6-9(14-2)10(8)15-3/h5-6H,1-4H3
  
The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07253,

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