Coumalic acid supplier | CasNO.500-05-0

Name
Coumalic acid
EINECS 207-899-0
CAS No. 500-05-0
Article Data18
CAS DataBase
Density 1.542 g/cm³
Solubility Very soluble in water.
Melting Point 203-205 °C (dec.)(lit.)
Formula C₆H₄O₄
Boiling Point 282.4 °C at 760 mmHg
Molecular Weight 140.095
Flash Point 137.3 °C
Transport Information
Appearance pale yellow to pale brown powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols Xi
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;
PSA 67.51000
LogP 0.33800

Synthetic route

: 6018-41-3
methyl coumalate

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

sodium formylacetic acid ester: sodium formylacetic acid ester

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

: 97-67-6
(S)-Malic acid

: 7664-93-9
sulfuric acid

A: 500-05-0
2H-pyran-2-one-5-carboxylic acid

B: 926-61-4
3-oxopropanoic acid

...Expand

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 74-85-1
ethene

: C8H8O4

Conditions

Conditions	Yield
In 1,4-dioxane at 110℃; for 16h; Kinetics; Temperature; Diels-Alder Cycloaddition;	98%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 5807-38-5
6-oxo-tetrahydro-pyran-3-carboxylic acid

Conditions

Conditions	Yield
With Raney nickel In methanol; toluene under 760.051 Torr; for 6h;	96.8%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: S-(1-butyn-3-yl)-O-methyl xanthate

: 6018-41-3
methyl coumalate

Conditions

Conditions	Yield
In toluene Heating;	92%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 149-73-5
trimethyl orthoformate

A: 114106-77-3
methyl 4-carbomethoxy-5-methoxy-penta-2(E),4(Z)-dienoate

B: 114106-78-4
methyl 3,5-dimethoxy-4-carbomethoxypent-4-enoate

Conditions

Conditions	Yield
With sulfuric acid In methanol for 48h; Heating;	A 89% B 6%

...Expand

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: tenofovir disoproxil

: tenofovir disoproxil coumalate

Conditions

Conditions	Yield
In hexane; dichloromethane at 20 - 40℃; Solvent; Temperature;	89%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 23090-18-8
2-oxo-2H-pyran-5-carbonyl chloride

Conditions

Conditions	Yield
With phosphorus pentachloride at 60℃; for 1h;	86%
With thionyl chloride at 100℃; for 8h;	84%
With phosphorus pentachloride at 60℃; for 1h;	80%

: 108-31-6
maleic anhydride

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 77802-48-3
bicyclo<2.2.2>oct-2-en-2,5-exo,6exo,7exo,8exo-pentacarbonsaeure-5,6:7,8-dianhydrid

Conditions

Conditions	Yield
at 200℃;	86%
at 200℃;	65%
at 200℃; Heating;

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 64-17-5
ethanol

: 5942-96-1
2-Oxo-2H-pyran-5-carbonseaure-ethylester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 18h; Ambient temperature;	86%
With trifluoromethylsulfonic anhydride; triethylamine; Triphenylphosphine oxide In 1,2-dichloro-ethane at 25℃; for 0.25h;	78%

: 592-76-7
1-Heptene

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 26311-45-5
4-pentylbenzoic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon In 1,3,5-trimethyl-benzene at 200℃; Diels-Alder reaction; regioselective reaction;	85%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 1443038-08-1
2-(2-chloro-4-(4-chlorobenzoyl)-6-fluorophenoxy)acetohydrazide

: [2-4-(4-chloro)benzoyl-2-chloro-6-fluorophenoxy]aceto-N(pyrone-2-one)carbonyl hydrazide

Conditions

Conditions	Yield
Stage #1: 2-(2-chloro-4-(4-chlorobenzoyl)-6-fluorophenoxy)acetohydrazide With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: 2H-pyran-2-one-5-carboxylic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; for 0.5h;	85%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 937037-30-4
cyclopropanecarboxylic acid (3-amino-1H-pyrazolo[3,4-d]thiazol-5-yl)-amide, trifluoroacetic acid

: 1-[5-(cyclopropanecarbonyl-amino)-1H-pyrazolo[3,4-d]thiazol-3-yl]-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With pyridine at 20℃; for 8h;	82%

: 67-56-1
methanol

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 6018-41-3
methyl coumalate

Conditions

Conditions	Yield
for 3h; Reflux;	81.8%
With sulfuric acid for 1h; Heating;	55%
With sulfuric acid

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 670221-21-3
2-(4-benzoylphenoxy)acetohydrazide

: 2-(4-benzoylphenoxy)aceto-N(pyrone-2-one)carbonylhydrazide

Conditions

Conditions	Yield
Stage #1: 2-(4-benzoylphenoxy)acetohydrazide With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: 2H-pyran-2-one-5-carboxylic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; for 0.5h;	81%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: C6H3ClO4

Conditions

Conditions	Yield
	80%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 125370-09-4
tetrakis[bis(trimethylsilyl)methyl]digallane(4)

: 1258211-75-4
Ga2(CH(SiMe3)2)2(2-oxo-2H-pyran-5-carboxylate)2

Conditions

Conditions	Yield
In tetrahydrofuran digallium compd. and acid suspended in THF at room temp.; suspn. stirred at room temp. for 16 h; volatiles removed in vacuo; residue washed with n-pentane;	79%

: 300-57-2
allylbenzene

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 620-86-0
4-Benzylbenzoic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon In 1,3,5-trimethyl-benzene at 200℃; Diels-Alder reaction; regioselective reaction;	79%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 1443038-11-6
2-[4-(4-methylbenzoyl)-2-chloro-6-fluorophenoxy]acethydrazide

: [2-4(-4-methyl)benzoyl-2-chloro-6-fluorophenoxy]aceto-N-(pyrone-2-one)carbonylhydrazide

Conditions

Conditions	Yield
Stage #1: 2-[4-(4-methylbenzoyl)-2-chloro-6-fluorophenoxy]acethydrazide With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: 2H-pyran-2-one-5-carboxylic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; for 0.5h;	78%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 165452-00-6
Dithiocarbonic acid O-[(3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester S-prop-2-ynyl ester

: 6-Oxo-6H-pyran-3-carboxylic acid (3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
In toluene Heating;	77%

: 186581-53-3, 908094-01-9
diazomethane

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 6018-41-3
methyl coumalate

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at 20℃; for 3h;	76.4%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

A: 19978-33-7
5-bromo-2H-pyran-2-one

B: 19978-41-7
3,5-dibromo-2H-pyran-2-one

Conditions

Conditions	Yield
With N-Bromosuccinimide; lithium acetate; tetrabutylammomium bromide In tetrachloromethane; acetonitrile at 65℃;	A n/a B 76%
With N-Bromosuccinimide; lithium acetate In water; acetonitrile at 20℃; for 72h; Product distribution; Further Variations:; Reaction partners; reagents ratios; Hundsdiecker reaction;	A 35% B 15%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 872-05-9
1-Decene

: 3575-31-3
4-octylbenzoic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon In 1,3,5-trimethyl-benzene at 200℃; Diels-Alder reaction; regioselective reaction;	72%
With palladium on activated charcoal In 1,3,5-trimethyl-benzene at 200℃; Diels-Alder Cycloaddition; Sealed tube;	72%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 1443038-07-0
[2-chloro-6-fluoro-4-(4-fluoro-benzoyl)-phenoxy]acetic acid hydrazide

: [2-4-(4-fluoro)benzoyl-2-chloro-6-fluorophenoxy]aceto-N-(pyrone-2-one)carbonylhydrazide

Conditions

Conditions	Yield
Stage #1: [2-chloro-6-fluoro-4-(4-fluoro-benzoyl)-phenoxy]acetic acid hydrazide With 2,6-dimethylpyridine In dichloromethane at 25 - 30℃; for 0.5h; Stage #2: 2H-pyran-2-one-5-carboxylic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 0 - 5℃; for 0.5h;	72%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 14111-43-4
1-methoxy-5,6,7,8-tetrafluorobenzobenzobarrelene

: 65-85-0
benzoic acid

Conditions

Conditions	Yield
In xylene at 200 - 205℃; for 4h; Product distribution; var. temp. and time;	71%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 187737-37-7
propene

A: 99-94-5
p-Toluic acid

B: 99-04-7
m-Toluic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; 5-methyl-dihydro-furan-2-one In toluene at 180℃; under 6723.1 Torr; for 8h; Reagent/catalyst; Solvent; Temperature; Time;	A 70.8% B 15.8%

...Expand

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 100-51-6
benzyl alcohol

: 61752-10-1
coumalic acid benzyl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 5h;	70%
With 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt for 15h; Heating;

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 821-95-4
1-undecene

: 38289-46-2
4-n-Nonylbenzoic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon In 1,3,5-trimethyl-benzene at 200℃; Diels-Alder reaction; regioselective reaction;	69%

: 500-05-0
2H-pyran-2-one-5-carboxylic acid

: 16519-24-7
1-(allyloxy)heptane

: 173265-17-3
4-((heptyloxy)methyl)benzoic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon In 1,3,5-trimethyl-benzene at 200℃; Diels-Alder reaction; regioselective reaction;	66%

Coumalic acid Chemical Properties

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

Coumalic acid 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.

Coumalic acid Safety Profile

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

Coumalic acid 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.

Product Name

Coumalic acid

Synthetic route

Coumalic acid Chemical Properties

Coumalic acid History

Coumalic acid Safety Profile

Coumalic acid Specification

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