3-CARBETHOXYUMBELIFERONE Chemical Properties

Melting point:

170.0 to 174.0 °C

Boiling point:

448.3±45.0 °C(Predicted)

Density 

1.397±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO: soluble5mg/mL, clear (warmed)

pka

7.32±0.20(Predicted)

form 

powder

color 

white to beige

λmax

398nm(EtOH)(lit.)

CAS DataBase Reference

6093-71-6

Safety Information

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

3-CARBETHOXYUMBELIFERONE Usage And Synthesis

Chemical Properties

Brown solid

Uses

Z9 is a potent inhibitor of PFKFB3, a member of 6-phosphofructo-2-kinases family. It avidly competes with fructose 6-phosphate (F6P) at PFKFB3. YZ9 is also cell permeable, inhibiting the growth of HeLa cells.

Biological Activity

YZ9 is a 5, 6, 7, 8-tetrahydroxy-2-(4-hydroxyphenyl) chromen-4-one (N4A) inhibitor.', 'YZ9 is a potent inhibitor of PFKFB3 (6-phosphfructo-2-kinase/fructose-2,6-bisphosphatase) with an IC50 = 183 nM. PFKFB3 is over expressed in many cancers and catalyzes the production of fructose-2,6-bisphosphate, which can potentiate PFK1 activity, enhancing glycolysis in tumor cells. YZ9 dose dependently inhibits proliferation of HeLa cells.

Synthesis

The general procedure for the synthesis of ethyl 7-hydroxy-2-oxo-2H-benzopyran-3-carboxylate from 2,4-dihydroxybenzaldehyde (3.70 mmol) and diethyl malonate (7.90 mmol) was as follows: piperidine (10 drops) was added to a solution of diethyl malonate of 2,4-dihydroxybenzaldehyde and the resulting mixture was stirred and reacted for 2 hours at room temperature. Upon completion of the reaction, the reaction mixture was acidified with 10% aqueous hydrochloric acid solution (5 mL). The precipitated solid was collected by filtration and washed with cold water (10 mL). The crude product was purified by fast column chromatography using dichloromethane:ethyl acetate (70:30, v/v) as eluent to afford the target compound ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate (0.735 g, 97% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) and 13C NMR (100 MHz, DMSO-d6): 1H NMR δ 1.28 (t, J = 7.1 Hz, 3H), 4.24 (q, J = 7.1 Hz, 2H), 6.71 (d, J = 1.8 Hz, 1H), 6.83 (dd, J = 1.8, 8.3 Hz, 1H), 7.74 (d, J = 8.3 Hz, 1H), 8.66 (s, 1H), 11.07 (s, 1H); 13C NMR δ 14.1, 60.8, 101.7, 110.4, 113.9, 120.0, 132.1, 149.4, 156.3, 157.0, 162.9, 164.0.

References

[1] Tetrahedron Letters, 2012, vol. 53, # 22, p. 2715 - 2718
[2] Patent: KR101744655, 2017, B1. Location in patent: Paragraph 0058-0060
[3] Patent: CN106279125, 2017, A. Location in patent: Paragraph 0039; 0040
[4] Letters in Organic Chemistry, 2013, vol. 10, # 7, p. 468 - 477
[5] Chemical Communications, 2017, vol. 53, # 11, p. 1813 - 1816

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