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500-05-0

Basic Information
CAS No.: 500-05-0
Name: Coumalic acid
Article Data: 18
Molecular Structure:
Molecular Structure of 500-05-0 (Coumalic acid)
Formula: C6H4O4
Molecular Weight: 140.095
Synonyms: Coumalicacid (6CI);Glutaconic acid, 4-(hydroxymethylene)-, d-lactone (7CI);2-Oxo-1(2H)-pyran-5-carboxylic acid;2-Oxo-2H-pyran-5-carboxylic acid;2-Oxopyran-5-carboxylic acid;2-Pentenedioicacid, 4-(hydroxymethylene)-, d-lactone;NSC 22978;a-Pyrone-5-carboxylic acid;
EINECS: 207-899-0
Density: 1.542 g/cm3
Melting Point: 203-205 °C (dec.)(lit.)
Boiling Point: 282.4 °C at 760 mmHg
Flash Point: 137.3 °C
Solubility: Very soluble in water.
Appearance: pale yellow to pale brown powder
Hazard Symbols: IrritantXi
Safety: 22-24/25
PSA: 67.51000
LogP: 0.33800
Synthetic route
6018-41-3

methyl coumalate

500-05-0

2H-pyran-2-one-5-carboxylic acid

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 80℃; for 18h;90%
97-67-6

(S)-Malic acid

500-05-0

2H-pyran-2-one-5-carboxylic acid

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 100℃; Reagent/catalyst; Temperature; Solvent; regioselective reaction;86%
617-48-1

malic acid

500-05-0

2H-pyran-2-one-5-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid at 80 - 90℃; for 3h;85%
With sulfuric acid Heating;67%
Stage #1: malic acid With fuming sulphuric acid In sulfuric acid at 75℃; for 6h;
Stage #2: In ice-cold water at 10℃; for 24h;
65%
97-67-6

(S)-Malic acid

A

500-05-0

2H-pyran-2-one-5-carboxylic acid

B

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With methanesulfonic acid In 1,2-dichloro-ethane at 100℃; Reagent/catalyst; Temperature; Solvent;A 14%
B 25%
97-67-6

(S)-Malic acid

5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

A

500-05-0

2H-pyran-2-one-5-carboxylic acid

B

926-61-4

3-oxopropanoic acid

sodium formylacetic acid ester

sodium formylacetic acid ester

500-05-0

2H-pyran-2-one-5-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid
97-67-6

(S)-Malic acid

7664-93-9

sulfuric acid

500-05-0

2H-pyran-2-one-5-carboxylic acid

114106-77-3

methyl 4-carbomethoxy-5-methoxy-penta-2(E),4(Z)-dienoate

10035-10-6, 12258-64-9

hydrogen bromide

500-05-0

2H-pyran-2-one-5-carboxylic acid

4-formyl-pentenedioic acid dimethyl ester

10035-10-6, 12258-64-9

hydrogen bromide

500-05-0

2H-pyran-2-one-5-carboxylic acid

Conditions
ConditionsYield
Kochen;
7664-93-9

sulfuric acid

sodium 3-ethoxy-3-oxoprop-1-en-1-olate

500-05-0

2H-pyran-2-one-5-carboxylic acid

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Chemistry

Molecule structure of Coumalic acid (CAS NO.500-05-0):

IUPAC Name: 6-Oxopyran-3-carboxylic acid
Molecular Weight: 140.09356 [g/mol]
Molecular Formula: C6H4O4 
Index of Refraction: 1.577
Molar Refractivity: 30.1 cm3
Molar Volume: 90.8 cm3
Surface Tension: 67 dyne/cm
Density: 1.542 g/cm3
Flash Point: 137.3 °C
Enthalpy of Vaporization: 57.36 kJ/mol
Boiling Point: 282.4 °C at 760 mmHg
Vapour Pressure: 0.000881 mmHg at 25°C
Melting Point: 203-205 °C (dec.)(lit.)
Merck: 14.2557
BRN: 119747
H-Bond Donor: 1
H-Bond Acceptor: 4
Rotatable Bond Count: 1
Exact Mass: 140.010959
MonoIsotopic Mass: 140.010959
Topological Polar Surface Area: 63.6
Heavy Atom Count: 10
Complexity: 236
Canonical SMILES: C1=CC(=O)OC=C1C(=O)O
InChI: InChI=1S/C6H4O4/c7-5-2-1-4(3-10-5)6(8)9/h1-3H,(H,8,9)
InChIKey: ORGPJDKNYMVLFL-UHFFFAOYSA-N
EINECS of Coumalic acid (CAS NO.500-05-0): 207-899-0

History

In 1785, Coumalic acid (CAS NO.500-05-0) was first isolated from apple juice by Carl Wilhelm Scheele. In 1787, Antoine Lavoisier  proposed the name acide malique which is derived from the Latin word for apple, mālum.

Safety Profile

Hazard Codes: IrritantXi
Safety Statements: 22-24/25
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

Specification

 Coumalic acid (CAS NO.500-05-0) is also named as 2-Oxopyran-5-carboxylic acid ; 2-Pentenedioic acid, 4-(hydroxymethylene)-, delta-lactone ; Cumalic acid ; alpha-Pyrone-5-carboxylic acid ; 2-Oxopyran-5-carboxylic acid ; 2H-Pyran-5-carboxylic acid, 2-oxo- . Coumalic acid (CAS NO.500-05-0) is pale yellow to pale brown powder. It is an active ingredient in many sour or tart foods. It is found mostly in unripe fruits.