5-ethoxy-3-(ethoxycarbonyl)-3-hydroxy-5-oxopentanoic acid

• ChemBase ID: 164811
• Molecular Formular: C10H16O7
• Molecular Mass: 248.22984
• Monoisotopic Mass: 248.08960285
• SMILES: O=C(CC(CC(=O)OCC)(C(=O)OCC)O)O
• Canonical SMILES: CCOC(=O)CC(C(=O)OCC)(CC(=O)O)O
• InChI: InChI=1S/C10H16O7/c1-3-16-8(13)6-10(15,5-7(11)12)9(14)17-4-2/h15H,3-6H2,1-2H3,(H,11,12)
• InChIKey: KGYXYKHTHJPEBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethoxy-3-(ethoxycarbonyl)-3-hydroxy-5-oxopentanoic acid
• IUPAC Traditional name: 5-ethoxy-3-(ethoxycarbonyl)-3-hydroxy-5-oxopentanoic acid
• Synonyms: 2-Hydroxy-1,2,3-propanetricarboxylic Acid 1,2-Diethyl Ester; 3-Hydroxy-3,4-bis(ethoxycarbonyl)butanoic Acid; Asym-Diethyl Citrate; Citric Acid 1,2-Diethyl Ester

Database IDs

• CAS Number: 19958-02-2
• PubChem SID: 162258945
• PubChem CID: 15384083

CALCULATED PROPERTIES

• Acid pKa: 3.994121
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.8324103
• LogD (pH = 7.4): -3.4797242
• Log P: -0.31728342
• Molar Refractivity: 54.6593 cm^3
• Polarizability: 22.081093 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C521020

Citric Acid 1,2-Diethyl Ester is an ethyl citrate found in lemon juice.

REFERENCES

• Neurath, G. et al.: Zeitsch. Lebens.-Untersuch. Forsch., 136, 284 (1968)