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4-Hydroxy-3-methoxycinnamic acid
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Name

4-Hydroxy-3-methoxycinnamic acid

 EINECS 214-490-0
CAS No. 1135-24-6 Density 1.316 g/cm3
PSA 66.76000 LogP 1.49860
Solubility Soluble in water Melting Point 168-172 °C(lit.)
Formula C10H10O4 Boiling Point 372.3 °C at 760 mmHg
Molecular Weight 194.187 Flash Point 150.5 °C
Transport Information N/A Appearance Pale Yellow Solid
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 1135-24-6 (Ferulic Acid) Hazard Symbols IrritantXi
Synonyms

2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-;(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate;3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid;3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid;caffeic acid 3-methyl ether;3-(4-Hydroxy-3-methoxyphenyl)acrylic acid;2-Propenoic acid,3-(4-hydroxy-3-methoxyphenyl)-;2-Propenoic acid, 3- (4-hydroxy-3-methoxyphenyl)-;Ferulate;3-Methoxy-4-hydroxy-trans-cinnamate;Cinnamic acid, 4-hydroxy-3-methoxy-;3-methoxy-4-hydroxycinnamic acid;Natural ferulic acid;Ferulic acid 99.5%;FerulicAcid;Gamma-Oryzanol, Ferulic acid;Fumalic acid;

Article Data 223

4-Hydroxy-3-methoxycinnamic acid Synthetic route

4046-02-0

ethyl 4-hydroxy-3-methoxycinnamate

1135-24-6

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

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 3h; Reflux;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 8h;98%
With Sporotrichum thermophile type C feruloyl esterase; water Enzyme kinetics;
With recombinant Tan410 In aq. phosphate buffer at 35℃; for 0.75h; pH=7; Enzymatic reaction;
141-82-2

malonic acid

121-33-5

vanillin

1135-24-6

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

Conditions
ConditionsYield
With piperidine; pyridine for 0.0833333h; microwave irradiation;94%
With piperidine; p-toluidine In toluene at 80℃; for 3h; Knoevenagel Condensation;94%
With bismuth(III) chloride for 0.0833333h; Doebner condensation; Microwave irradiation; Neat (no solvent);93%

(E)-methoxymethyl 3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylate

1135-24-6

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

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water at 20℃; for 0.416667h;90%
2309-07-1

Methyl ferulate

1135-24-6

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

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox;89%
With Sporotrichum thermophile type C feruloyl esterase; water Enzyme kinetics;
141-82-2

malonic acid

148-53-8

3-methoxy-2-hydroxybenzaldehyde

1135-24-6

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

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 60℃; for 8h; Knoevenagel-Doebner condensation;83%
98885-93-9, 115851-80-4, 147556-16-9

curcumin

A

1135-24-6

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

B

121-33-5

vanillin

C

(1E,4Z,8Z,11E)-5,8-Dihydroxy-1,12-bis-(4-hydroxy-3-methoxy-phenyl)-6,7-bis-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-dodeca-1,4,8,11-tetraene-3,10-dione

Conditions
ConditionsYield
With 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride; dihydrogen peroxide; acetylacetone In dichloromethane at 20℃; for 2.5h;A 2.1%
B 3.3%
C 70%

C10H9IO3

1135-24-6

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

Conditions
ConditionsYield
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 120℃; for 6h;60%
85364-70-1

3-methyl-4-nitro-5-<2-(3-methoxy-4-hydroxyphenyl)ethenyl>isoxazole

1135-24-6

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

Conditions
ConditionsYield
With sodium hydroxide for 2h; Heating;49.7%
331-39-5

caffeic acid

S-(5’-adenosyl)-L-methionine chloride

1135-24-6

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

Conditions
ConditionsYield
O-methyltransferase pH 7;
63644-62-2, 123821-69-2, 62706-35-8

(E,E)-3-(4-hydroxy-3-methoxyphenyl)allyl 3-(4-hydroxy-3-methoxyphenyl)acrylate

A

1135-24-6

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

B

458-35-5, 32811-40-8, 69056-21-9

coniferal alcohol

C

63644-71-3

(E)-4-(3-methoxy-1-propenyl)-2-methoxyphenol

Conditions
ConditionsYield
Product distribution; hydrolysis by various reaction conditions to various product;

4-Hydroxy-3-methoxycinnamic acid Chemical Properties

IUPAC Name: (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid 
Empirical Formula: C10H10O4
Molecular Weight: 194.184g/mol
EINECS: 208-679-7 
Structure of 4-Hydroxy-3-methoxycinnamic acid (CAS NO.1135-24-6):

Index of Refraction: 1.626
Molar Refractivity: 52.26 cm3
Molar Volume: 147.4 cm3
Polarizability: 20.72×10-24cm3
Surface Tension: 56.1 dyne/cm
Density: 1.316 g/cm3
Flash Point: 150.5 °C
Enthalpy of Vaporization: 65.35 kJ/mol 
Melting Point: 168-172 °C(lit.)
Boiling Point: 372.3 °C at 760 mmHg
Vapour Pressure: 3.34E-06 mmHg at 25°C 
Water Solubility: soluble 
Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Cinnamic Acids, Esters and Derivatives;Aromatics 
Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)O)O
Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)O)O
InChI: InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChIKey: KSEBMYQBYZTDHS-HWKANZROSA-N

4-Hydroxy-3-methoxycinnamic acid Uses

1.It is an antioxidant in the sense that it is reactive toward free radicals such as reactive oxygen species (ROS). ROS and free radicals are implicated in DNA damage, cancer, accelerated cell aging.
2.It may have pro-apoptotic effects in cancer cells, thereby leading to their destruction.
3.It may be effective at preventing cancer induced by exposure to the carcinogenic compounds benzopyreneand 4-nitroquinoline 1-oxide.

4-Hydroxy-3-methoxycinnamic acid Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intraperitoneal > 350mg/kg (350mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: REGIDITY		 Indian Journal of Pharmaceutical Sciences. Vol. 49, Pg. 77, 1987.
mouse LD50 intravenous 857mg/kg (857mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 38, Pg. 1620, 1990.

4-Hydroxy-3-methoxycinnamic acid Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: UD3365500
Hazard Note: Irritant
Hazardous Substances Data: 1135-24-6(Hazardous Substances Data)

4-Hydroxy-3-methoxycinnamic acid Specification

  4-Hydroxy-3-methoxycinnamic acid , its cas register number is 1135-24-6. It also can be called 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid ; 3-Methoxy-4-hydroxycinnamic acid ; 4-Hydroxy-3-methoxy cinnamic acid ; CCRIS 3256 ; Cinnamic acid, 4-hydroxy-3-methoxy- ; Coniferic acid ; Ferulic acid .
 4-Hydroxy-3-methoxycinnamic acid (CAS NO.1135-24-6) is a pale yellow solid.

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