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2309-07-1

Basic Information
CAS No.: 2309-07-1
Name: FERULIC ACID METHYL ESTER
Article Data: 156
Molecular Structure:
Molecular Structure of 2309-07-1 (FERULIC ACID METHYL ESTER)
Formula: C11H12O4
Molecular Weight: 208.214
Synonyms: Cinnamic acid,4-hydroxy-3-methoxy-, methyl ester (6CI,7CI,8CI);Ferulic acid methyl ester;Methyl 4'-hydroxy-3'-methoxycinnamate;Methyl ferulate;NSC 74548;
EINECS: 1308068-626-2
Density: 1.205 g/cm3
Melting Point: 62-65 °C
Boiling Point: 338.077 °C at 760 mmHg
Flash Point: 130.409 °C
Solubility: Slightly soluble in water.
Risk Codes: 36/37/38
Safety: 26-36/37/39
PSA: 55.76000
LogP: 1.58700
Synthetic route
67-56-1

methanol

1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With Dowex 50 W x 8200-400 Heating;100%
With thionyl chloride Ambient temperature;100%
With sulfuric acid at 0℃; for 12h; Darkness; Reflux;99%
220300-07-2

methyl (E)-4-methoxymethyl-3-methoxycinnamate

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.5h; Heating;100%
121-33-5

vanillin

21204-67-1

methyl (triphenylphosphoranylidene)acetate

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
In water at 90℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Green chemistry;99%
In toluene at 150℃; for 0.166667h; Wittig Olefination; Inert atmosphere; Microwave irradiation; Sealed tube; stereoselective reaction;98%
In toluene at 150℃; for 0.166667h; Sealed tube; Microwave irradiation;98%
67-56-1

methanol

92446-10-1

[(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acryloyloxymethylene]-dimethyl-ammonium; chloride

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
98%
67-56-1

methanol

1135-24-6

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With sulfuric acid for 4h; Reflux;96%
With sulfuric acid Fischer-Speier Esterification; Sealed tube; Heating; Microwave irradiation;

3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyldiazonium tetrafluoroborate

292638-85-8

acrylic acid methyl ester

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With palladium diacetate In methanol at 20℃; Heck Reaction;96%

(E)-methyl 3-(4-(((2'-cyanobiphenyl-4-yl)methyl)diisopropylsilyloxy)-3-methoxyphenyl)acrylate

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;94%
259267-38-4

methyl (E)-3-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)acrylate

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2h;90%
97-54-1

2-methoxy-4-propenylphenol

292638-85-8

acrylic acid methyl ester

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;90%
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With sulfuric acid In methanol at 20℃; for 4h;84%
Multi-step reaction with 2 steps
2: 98 percent
View Scheme
With sulfuric acid In methanol; ice-water; diethyl ether; dichloromethane
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetonitrile / 18 h / 70 °C / Inert atmosphere
1.2: 24 h / 660 °C / Inert atmosphere
2.1: methanol / 18 h / 20 °C / Inert atmosphere
3.1: bis-triphenylphosphine-palladium(II) chloride; ammonium formate / acetonitrile / 24 h / 80 °C / Inert atmosphere
View Scheme
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Specification

The CAS register number of Methyl 4-hydroxy-3-methoxycinnamate is 2309-07-1. It also can be called as Methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate and the IUPAC name about this chemical is methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate. The molecular formula about this chemical is C11H12O4 and the molecular weight is 208.21. It belongs to the Aromatic Esters.

Physical properties about Methyl 4-hydroxy-3-methoxycinnamate are: (1)ACD/LogP: 1.41; (2)ACD/LogD (pH 5.5): 1.4; (3)ACD/LogD (pH 7.4): 1.39; (4)ACD/BCF (pH 5.5): 6.88; (5)ACD/BCF (pH 7.4): 6.66; (6)ACD/KOC (pH 5.5): 138.41; (7)ACD/KOC (pH 7.4): 134.04; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 44.76Å2; (12)Index of Refraction: 1.574; (13)Molar Refractivity: 57.11 cm3; (14)Molar Volume: 172.8 cm3; (15)Polarizability: 22.64x10-24cm3; (16)Surface Tension: 44.5 dyne/cm; (17)Enthalpy of Vaporization: 60.44 kJ/mol; (18)Boiling Point: 338.1 °C at 760 mmHg; (19)Vapour Pressure: 5.13E-05 mmHg at 25°C.

Uses of Methyl 4-hydroxy-3-methoxycinnamate: it can be used to produce 3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid 2,3,4,5,6-pentahydroxy-hexyl ester with D-mannitol. This reaction will need reagent K2CO3 and solvent dimethylformamide. The yield is about 30.4%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)\C=C\c1cc(OC)c(O)cc1
(2)InChI: InChI=1/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4+
(3)InChIKey: AUJXJFHANFIVKH-GQCTYLIABZ
(4)Std. InChI: InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4+
(5)Std. InChIKey: AUJXJFHANFIVKH-GQCTYLIASA-N

The toxicity data is as follows:
 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1189mg/kg (1189mg/kg)   Indian Journal of Experimental Biology. Vol. 25, Pg. 187, 1987.