Coumalic acid Chemical Properties

Melting point:

203-205 °C (dec.) (lit.)

Boiling point:

218 °C/120 mmHg (lit.)

Density 

1.2154 (rough estimate)

refractive index 

1.4434 (estimate)

Flash point:

218°C/120mm

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.80±0.20(Predicted)

color 

White to Light yellow to Light orange

Water Solubility 

Very soluble in water.

Merck 

14,2557

BRN 

119747

LogP

0.411 (est)

CAS DataBase Reference

500-05-0(CAS DataBase Reference)

NIST Chemistry Reference

2H-Pyran-5-carboxylic acid, 2-oxo-(500-05-0)

EPA Substance Registry System

2H-Pyran-5-carboxylic acid, 2-oxo- (500-05-0)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29322090

MSDS

• Language:English Provider:2-Oxo-2H-pyran-5-carboxylic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Coumalic acid Usage And Synthesis

Chemical Properties

pale yellow to pale brown powder

Uses

Coumalic acid undergoes thermal reaction with 1,3-butadiene to yield dimethyl tricycle[3.2.1.02,7]oct-3-ene-2,4-dicarboxylate.

Definition

ChEBI: Coumalic acid is a pyranone.

General Description

Decarboxylates to α-pyrone, a Diels-Alder diene.

Synthesis

The general procedure for the synthesis of coumaric acid from DL-malic acid was as follows: fuming sulfuric acid (287 g) was slowly added dropwise over a period of 2 hours to a suspension of DL-malic acid (200 g) dissolved in concentrated sulfuric acid (313 g) at 75 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at the same temperature for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured slowly into ice water over a period of 1 hour. After stirring for 15 minutes, the mixture was left to stand overnight. On the following day, the mixture was cooled to below 10°C and the coumaric acid crude product was isolated by filtration. After washing and drying, coumaric acid was obtained (71 g, 95% purity, 65% yield).

Purification Methods

The acid crystallises from MeOH. The methyl ester has m 73-74o (from pet ether) and b 178-180o/60 mm. [Beilstein 18/8 V 120.]

References

[1] Liebigs Annalen der Chemie, 1990, p. 233 - 238
[2] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 1, p. 229 - 234
[3] Patent: WO2004/792, 2003, A1. Location in patent: Page 15
[4] Organic Process Research and Development, 2003, vol. 7, # 1, p. 74 - 81
[5] Patent: CN103788039, 2016, B. Location in patent: Paragraph 0039; 0041-0044

Coumalic acid(500-05-0)Related Product Information

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