7-HYDROXYCOUMARIN-3-CARBOXYLIC ACID Chemical Properties

Melting point:

261 °C(lit.)

Boiling point:

474.8±45.0 °C(Predicted)

Density 

1.639±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

solubility 

DMF: soluble

pka

7.04 ± 0.02, temperature: 23 °C

form 

powder to crystal

color 

Yellow solid;Orange solid; Off-white powder

λmax

386 nm (Buffer pH 10.0); 339 nm (Buffer pH 4.0)

BRN 

384141

Major Application

Carbon-dioxide sensor; chemical sensors based on non-linear optics; monitoring of cationic photopolymerization processes; nanomaterials

Biological Applications

Chemical dosimeter for radiation therapy; detecting bacteria; detecting/sensing hydroxyl radicals; studying nucleic acids; as a substrate for measuring carboxylesterases activity, cellulases activity, β-galactosidases activity, glycosidases activity, glycosyltransferases activity, hydrolases activity, 4-hydroxycinnamate decarboxylases activity, β-lactamases activity, phosphatases activity, sulfatases activity; treating cancer/antitumor activity

InChI

InChI=1S/C10H6O5/c11-6-2-1-5-3-7(9(12)13)10(14)15-8(5)4-6/h1-4,11H,(H,12,13)

InChIKey

LKLWLDOUZJEHDY-UHFFFAOYSA-N

SMILES

C1(=O)OC2=CC(O)=CC=C2C=C1C(O)=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich

7-HYDROXYCOUMARIN-3-CARBOXYLIC ACID Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

7-Hydroxycoumarin-3-carboxylic acid is a pH-indicator that can be immobilized on a support to give a pH sensor.

Uses

Suitable as pH-indicator.

Synthesis

General procedure for the synthesis of 7-hydroxy-2-oxo-2H-benzopyran-3-carboxylic acid from ethyl 7-hydroxy-2-oxo-2H-benzopyran-3-carboxylate: ethyl 7-hydroxy-2-oxo-2H-benzopyran-3-carboxylate (2.00 g, 8.55 mmol) was dissolved in water (20 ml) at 90 °C and concentrated hydrochloric acid (6 ml) was added slowly. The reaction mixture was refluxed for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the precipitate was collected by filtration and washed with cold water to obtain 7-hydroxy-2-oxo-2H-benzopyran-3-carboxylic acid (1.32 g, 6.41 mmol) as a light red solid in 75% yield.

References

[1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 638 - 639
[2] Food Chemistry, 2012, vol. 135, # 4, p. 2872 - 2878
[3] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 502 - 506
[4] Chemical Communications, 2017, vol. 53, # 11, p. 1813 - 1816
[5] Patent: CN106279125, 2017, A. Location in patent: Paragraph 0041; 0042

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