| Identification | More | [Name]
Coumalic acid | [CAS]
500-05-0 | [Synonyms]
2-OXO-2H-PYRAN-5-CARBOXYLIC ACID
2-PYRONE-5-CARBOXYLIC ACID
ALPHA-PYRONE-5-CARBOXYLIC ACID
COUMALIC ACID
CUMALIC ACID
CUMALINIC ACID
TIMTEC-BB SBB004170
2-Oxo-1,2H-pyran-5-carboxylic acid
2-oxo-2h-pyran-5-carboxylicaci
2-Oxopyran-5-carboxylic acid
2-Pentenedioic acid, 4-(hydroxymethylene)-, delta-lactone
alpha-Pyrone-3-carboxylic acid
Coumalicacid,97%
6-oxo-6H-pyran-3-carboxylic acid
2-Oxo-2H-pyran-5-carboxylic acid, 2-Pyrone-5-carboxylic acid
6-Oxopyran-3-carboxylic acid
a-Pyrone-5-carboxylic acid
α-Pyrone-5-carboxylic acid | [EINECS(EC#)]
207-899-0 | [Molecular Formula]
C6H4O4 | [MDL Number]
MFCD00006644 | [Molecular Weight]
140.09 | [MOL File]
500-05-0.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29322090 |
| Hazard Information | Back Directory | [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 |
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