3-Hydroxy-4-methoxycinnamic acid Chemical Properties

Melting point:

230 °C (dec.)(lit.)

Boiling point:

250.62°C (rough estimate)

Density 

1.0583 (rough estimate)

refractive index 

1.5168 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in ethanol and methanol.

pka

4.53±0.10(Predicted)

form 

Solid

color 

Pale Yellow

BRN 

2212760

InChI

InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)

InChIKey

QURCVMIEKCOAJU-UHFFFAOYSA-N

SMILES

C(O)(=O)C=CC1=CC=C(OC)C(O)=C1

LogP

0.788 (est)

CAS DataBase Reference

537-73-5(CAS DataBase Reference)

NIST Chemistry Reference

Cinnamic acid, 3-hydroxy-4-methoxy-(537-73-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

2

RTECS 

UD3365400

Hazard Note 

Irritant

HS Code 

29189090

MSDS

• Language:English Provider:3-Hydroxy-4-methoxycinnamic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Hydroxy-4-methoxycinnamic acid Usage And Synthesis

Chemical Properties

Off-White Crystalline Solid

Uses

3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent.

Uses

3-Hydroxy-4-methoxycinnamic acid exhibits hypoglycemic properties.

Uses

3-Hydroxy-4-methoxycinnamic acid was used in the synthesis of tranilast and various tranilast analogs (cinnamoyl anthranilates) by genetically engineered Saccharomyces cerevisiae yeast strain. It was also used in the synthesis of glycoside compounds by undergoing glycosidation.

Definition

ChEBI: A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.

General Description

3-Hydroxy-4-methoxycinnamic acid, predominantly trans is available as white crystals. 3-Hydroxy-4-methoxycinnamic acid is isolated from the aerial part of Artemisia capillaris, Chinese medicinal plant. It is a component of chinese herbal medicine used for a pain killer and stomachic. It is an efficient acetylcholine inhibitor. 3-Hydroxy-4-methoxycinnamic acid is bioactive metabolite of Spilanthes acmella Murr. It increases the resistance of low-density lipoprotein (LDL) to oxidation.

Synthesis

To a suspension of isovanillin (152 mg, 1.00 mmol) and malonic acid (416 mg, 4.00 mmol) in toluene (5 mL) was added triethylamine (0.70 mL, 5.00 mmol) and N,N-dimethylformamide dimethyl acetal (0.20 mL, 1.50 mmol). The reaction mixture was heated to reflux for 4 hours, subsequently cooled to room temperature and concentrated on a rotary evaporator. The residue was dissolved in 1 M NaOH solution (20 mL) and the resulting solution was washed with dichloromethane (3 x 20 mL). The aqueous phase was acidified to pH 1 by the addition of 3 M HCl. The milky precipitate formed was collected in a Hirsch funnel, washed with dilute hydrochloric acid and air dried. The precipitate was recrystallized by solvent recrystallization in a methanol-water mixture and dried in a vacuum desiccator using phosphorus pentoxide as a drying agent to give trans-3-hydroxy-4-methoxycinnamic acid (164 mg, 85% yield) as a cream-colored crystalline solid.1H NMR spectroscopic data were in agreement with those reported in the literature (McCorkindale, N.J.; McCulloch, A.W. Magrill, D.S.; Caddy, B.; Martin-Smith, M.; Smith, S.J.; Stenlake, J.B. Tetrahedron 1969, 25, 5475).

IC 50

α adrenergic receptor

References

[1] Synthetic Communications, 1995, vol. 25, # 20, p. 3187 - 3197
[2] Chemical Communications, 1998, # 21, p. 2335 - 2336
[3] Tetrahedron, 2007, vol. 63, # 4, p. 960 - 965
[4] Tetrahedron Letters, 2012, vol. 53, # 20, p. 2537 - 2539
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2707 - 2713

3-Hydroxy-4-methoxycinnamic acid(537-73-5)Related Product Information

• trans-Cinnamic acid
• 3-Hydroxycinnamic acid
• 4-Hydroxycinnamic acid
• CHLOROPHOSPHONAZO III
• N-BUTYL CINNAMATE
• Methyl cinnamate
• alpha-Methylcinnamic acid
• Ethyl cinnamate
• 3,4-Dimethoxycinnamonitrile
• 4-Methoxycinnamic acid
• HYDROXYCINNAMIC ACID
• 3,4-(Methylenedioxy)cinnamic acid
• 2-BROMO-4,5-METHYLENEDIOXYCINNAMIC ACID
• 3,4,5-TRIMETHOXYCINNAMIC ACID ETHYL ESTER
• 4,5-DIMETHOXY-2-NITROCINNAMIC ACID
• trans-2,3,4-Trimethoxycinnamic acid
• 2-BROMO-4,5-DIMETHOXYCINNAMIC ACID
• trans-2,4,5-Trimethoxycinnamic acid