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- YZ9
-
- $50.00
-
2026-08-08
- CAS:6093-71-6
- Purity: 99.59%
- Supply Ability: 10g
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| | 3-Carbethoxyumbeliferone Basic information |
| Product Name: | 3-Carbethoxyumbeliferone | | Synonyms: | AURORA 9226;ETHYL 3-UMBELLIFERYLCARBOXYLATE;7-HYDROXYCOUMARIN-3-CARBOXYLIC ACID ETHYL ESTER;AKOS BBS-00008132;UMBELLIFERONE 3-CARBOXYLIC ACID ETHYL ESTER;Ethyl 7-hydroxy-2-oxo-2H-chroMene-3-carboxylate;Ethyl 7-Hydroxycoumarin-3-carboxylate;3-CARBETHOXYUMBELIFERONE7-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester | | CAS: | 6093-71-6 | | MF: | C12H10O5 | | MW: | 234.2 | | EINECS: | | | Product Categories: | Aromatic Esters | | Mol File: | 6093-71-6.mol |  |
| | 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.) | | InChI | 1S/C12H10O5/c1-2-16-11(14)9-5-7-3-4-8(13)6-10(7)17-12(9)15/h3-6,13H,2H2,1H3 | | InChIKey | IETDBZQIWIJQJG-UHFFFAOYSA-N | | SMILES | [o]1c2c(cc([c]1=O)C(=O)OCC)ccc(c2)O | | CAS DataBase Reference | 6093-71-6 |
| WGK Germany | 3 | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids |
| | 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 |
| | 3-Carbethoxyumbeliferone Preparation Products And Raw materials |
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