Dibenzylideneacetone

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

What is the Dibenzylideneacetone?

The molecule Dibenzylideneacetone presents a molecular formula of C17H14O and its IUPAC name is dibenzylideneacetone.

Dibenzylideneacetone (DBA) is a molecule with the formula C10H10O. It is a white solid that is soluble in organic solvents. It is used as a reagent in organic synthesis..

DBA was first reported in 1907 by A. von Baeyer and W. H. Caro. They prepared it by condensation of acetone with benzaldehyde in the presence of sodium ethoxide..

DBA is prepared by the condensation of acetone with benzaldehyde..

The reaction is catalyzed by base, such as sodium ethoxide..

DBA is a versatile reagent in organic synthesis. It has been used in the synthesis of various molecules, including drugs, dyes, and pigments..

DBA is also used as a cross-linking agent in the production of polyurethanes..

3D structure

Cartesian coordinates

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

2D drawing

 

Dibenzylideneacetone WMKGGPCROCCUDY-PHEQNACWSA-N chemical compound 2D structure molecule svg
Dibenzylideneacetone

 

Molecule descriptors

 
IUPAC namedibenzylideneacetone
InChI codeInChI=1S/C13H24O4/c1-3-16-12(14)10-8-6-5-7-9-11-13(15)17-4-2/h3-11H2,1-2H3
InChI KeyWMKGGPCROCCUDY-PHEQNACWSA-N
SMILESC(=C\c1ccccc1)/C(=O)/C=C/c1ccccc1

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

There exist several different chemical codes commonly used in orded to identify molecules:

Physico-Chemical properties

IUPAC namedibenzylideneacetone
Molecular formulaC17H14O
Molecular weight234.292
Melting point (ºC)110
Boiling point (ºC)-
Density (g/cm3)-
Molar refractivity75.96
LogP4.0
Topological polar surface area52.6

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

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow 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(Kow) (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 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.