Diethyl cromoglycate CAS#: 16150-45-1; ChemWhat Code: 156774
Identification
| Product Name | Diethyl cromoglycate |
| IUPAC Name | ethyl 5-[3-(2-ethoxycarbonyl-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylate |
| Molecular Structure |  |
| CAS Registry Number | 16150-45-1 |
| Synonyms | Diethyl cromoglycate 16150-45-1 Cromophene Diethyl 5,5′-((2-hydroxypropane-1,3-diyl)bis(oxy))bis(4-oxo-4H-chromene-2-carboxylate) SMU3BJ0QSN ethyl 5-[3-(2-ethoxycarbonyl-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylate Cromoglycic acid diethyl ester Diethyl 5,5′-((2-hydroxypropane-1,3-diyl)-bis(oxy))bis(4-oxo-4H-chromene-2-carboxylate) 4H-1-Benzopyran-2-carboxylic acid, 5,5′-[(2-hydroxy-1,3-propanediyl)bis(oxy)]bis[4-oxo-, 2,2′-diethyl ester BRN 1337752 UNII-SMU3BJ0QSN EC 605-256-2 4H-1-Benzopyran-2-carboxylic acid, 5,5′-((2-hydroxy-1,3-propanediyl)bis(oxy))bis(4-oxo-, diethyl ester SCHEMBL143979 1,3-Bis(2-ethoxycarbonylchromon-5-yloxy)-2-hydroxypropan DTXSID20167164 KRBBSLDXYDBFEC-UHFFFAOYSA-N AC-126 MFCD01762791 AKOS015963154 AS-15223 CS-0151767 FT-0649063 NS00008787 D94547 SODIUM CROMOGLICATE IMPURITY B [EP IMPURITY] diethyl 5,5′-(2-hydroxypropane-1,3-diyl)bis(oxy)bis(4-oxo-4H-chromene-2-carboxylate) 5,5′-[(2-hydroxytrimethylene)dioxy]bis [4-oxo-4H-1-benzopyran-2-carboxylic acid] diethyl ester Diethyl 5,5′-[(2-hydroxypropane-1,3-diyl)bis(oxy)]bis(4-oxo-4H-chromene-2-carboxylate), Diethyl cromoglycate |
| Molecular Formula | C27H24O11 |
| Molecular Weight | 524.5 |
| InChI | InChI=1S/C27H24O11/c1-3-33-26(31)22-11-16(29)24-18(7-5-9-20(24)37-22)35-13-15(28)14-36-19-8-6-10-21-25(19)17(30)12-23(38-21)27(32)34-4-2/h5-12,15,28H,3-4,13-14H2,1-2H3 |
| InChI Key | KRBBSLDXYDBFEC-UHFFFAOYSA-N |
| Isomeric SMILES | CCOC(=O)C1=CC(=O)C2=C(O1)C=CC=C2OCC(COC3=CC=CC4=C3C(=O)C=C(O4)C(=O)OCC)O |
Physical Data
No data available
| Melting Point, °C |
| 154 – 156 |
| 186 |
| 180 – 182 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | |
| Chemical shifts | 1H | chloroform-d1 | 300 |
| Chemical shifts | 1H | CDCl3 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands | KBr | 1650 cm**(-1) |
Route of Synthesis (ROS)
| Conditions | Yield |
| With hydrogenchloride at 95 – 100℃; for 28h; Inert atmosphere; | 80% |
| With hydrogenchloride In lithium hydroxide monohydrate at 100℃; for 24h; Sealed tube; Experimental Procedure 3 5,5’- [(2-Hydroxy- 1.3 -propanediyl)bi s(oxy)lbi s [4-oxo-4H- 1 -benzopyran-2- carboxylic acid diethyl ester A suspension of cromolyn sodium salt (1.0 g, 2 mmol) in EtOH (100 mL) and con. HC1 (1 mL) was heated in a sealed reactor tube for 24 h at 100°C. The white solid was dissolved to give a clear colorless solution while hot. It was allowed to cool to room temperature and NaHCO3 (1.0 g) was added. After stirring for 30 mm at 25°C, solvent was removed by roto-evaporation. Chromatography on silica gel of the crude material using 5:95 methanol/methylene chloride yielded the diethyl ester (0.8 g, 76 % yield); mp 154-156°C; ‘HNIVIR (CDC13, 300 MHz) 1.42 (t, 3H, J=7.1 Hz, CH3), 2.73 (br s, 1H, OH), 4.44 (q, 4H, J=7.1 Hz, 2OCH2CH3), 4.32-4.59 (m, 5H, CHOH, 20CH2), 6.80 (s, 2H, 2 vinyl-H), 6.99 (d, 2H, J=8.24Hz, 2Aro-H), 7.12 (d, 2H, J=8.24Hz, 2Aro-H), 7.17 (d, 2H, J=8.24Hz, 2Aro-H),7.71 (t, 2H, J=8.24 2Aro-H). | 76% |
| With hydrogenchloride In lithium hydroxide monohydrate at 100℃; for 24h; Sealed tube; | 76% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal] H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation] |
| Precautionary Statement Codes | P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
No data available
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 524.481 |
| logP | 3.05 |
| HBA | 7 |
| HBD | 1 |
| Matching Lipinski Rules | 3 |
| Veber rules component | |
| Polar Surface Area (PSA) | 143.89 |
| Rotatable Bond (RotB) | 12 |
| Matching Veber Rules | 0 |
| Use Pattern |
| Diethyl cromoglycate CAS#: 16150-45-1 used be a intermediate of API Sodium Cromoglycate. It is also named 1,3-BIS(2-ETHOXYCARBONYLCHROMON-5-YLOXY)-2-HYDROXYPROPAN:DIETHYLCROMOGLYCATE; 5-[3-(2-carbethoxy-4-keto-chromen-5-yl)oxy-2-hydroxy-propoxy]-4-keto-chromene-2-carboxylicacidethylester;ethyl5-[3-(2-ethoxycarbonyl-4-oxo-chromChemicalbooken-5-yl)oxy-2-hydroxy-propoxy]-4-oxo-chromene-2-carboxylate;ethyl5-[3-(2-ethoxycarbonyl-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylate;Diethyl5,5′-((2-hydroxypropane-1,3-diyl)-bis(oxy))bis(4-oxo-4H-chromene-2-carboxylate). And it is often used as a food coloring additive to give food a vibrant color and enhance its visual appeal. It is commonly used in the production of candies, pastries, confectionery, beverages, and other food products. |
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