Ethyl Acetoacetate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Ethyl Acetoacetate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Ethyl Acetoacetate?

The molecule Ethyl Acetoacetate presents a molecular formula of C₆H₁₀O₃ and its IUPAC name is ethyl acetoacetate.

Ethyl acetoacetate is an organic compound with the chemical formula CH3COCH2CO2Et. It is a colorless liquid with a fruity odor. It is produced by the reaction of acetoacetic acid and ethanol..

Ethyl acetoacetate is used as a solvent and as a precursor to other chemicals. It is used in the manufacture of dyes, pharmaceuticals, and perfumes. It is also used as a food flavoring and as a nail polish remover..

The compound is a member of the class of compounds known as ketones. Ketones are compounds in which a carbon atom is bonded to two other carbon atoms, one of which is bonded to an oxygen atom. Ethyl acetoacetate contains two ketone groups..

The compound is soluble in water and insoluble in organic solvents. It is flammable and has a low flash point..

Ethyl acetoacetate is produced by the reaction of acetoacetic acid and ethanol. The reaction is catalyzed by an enzyme called acetoacetate decarboxylase..

Acetoacetic acid is produced by the action of bacteria on carbohydrates. It is also produced by the action of certain enzymes on fats..

Ethanol is produced by the fermentation of sugars. It is also produced by the distillation of certain types of fruits and vegetables..

The reaction of acetoacetic acid and ethanol produces ethyl acetoacetate and carbon dioxide..

Ethyl acetoacetate can also be produced by the reaction of ketones with alcohols. This reaction is called esterification..

Ethyl acetoacetate is a clear, colorless liquid with a fruity odor. It is insoluble in water, but soluble in most organic solvents. It is flammable and has a low flash point..

3D structure

Cartesian coordinates

Geometry of Ethyl Acetoacetate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

Molecule descriptors

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

Reference codes for other databases

• CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
• Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
• ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
• PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
• RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
• ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
• CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.

Physico-Chemical properties

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (K_ow) data is applied in toxicology and drug research. K_ow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(K_ow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Ų are required. Thus, molecules with a polar surface area greater than 140 Ų tend to be poorly permeable to cell membranes.