Bisphenol A

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

What is the Bisphenol A?

The molecule Bisphenol A presents a molecular formula of C15H16O2 and its IUPAC name is bisphenol A.

Bisphenol A (BPA) is an organic compound with the chemical formula (CH3)2C(C6H4OH)2. It is a colorless solid that is soluble in organic solvents and has a wide variety of applications. BPA is used to make polycarbonate plastics and epoxy resins. These materials are used in a variety of consumer products, including food and beverage containers, water bottles, sports equipment, and medical devices. BPA is also present in some thermal paper products, such as receipts, and in certain dental sealants and composites..

Exposure to BPA is widespread in the general population. BPA can be released from polycarbonate plastic and epoxy resin into the environment and into food and beverages. BPA has been measured in the urine of 95% of the U.S. population..

BPA has been shown to be an endocrine disruptor in animals. BPA can mimic the hormone estrogen and can bind to estrogen receptors in the body. BPA exposure has been linked to a variety of health effects, including reproductive and developmental toxicity, cancer, diabetes, and obesity..

The European Union has banned the use of BPA in baby bottles, and Canada has declared BPA a toxic substance. In the United States, the Food and Drug Administration has banned the use of BPA in baby bottles and infant formula containers, but the chemical is still used in other food and beverage containers, as well as in many other consumer products..

3D structure

Cartesian coordinates

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

2D drawing

 

Bisphenol A IISBACLAFKSPIT-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Bisphenol A

 

Molecule descriptors

 
IUPAC namebisphenol A
InChI codeInChI=1S/C11H14O2/c1-2-3-9-13-11(12)10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3
InChI KeyIISBACLAFKSPIT-UHFFFAOYSA-N
SMILESC(c1ccc(cc1)O)(c1ccc(cc1)O)(C)C

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 namebisphenol A
Molecular formulaC15H16O2
Molecular weight228.286
Melting point (ºC)159
Boiling point (ºC)-
Density (g/cm3)-
Molar refractivity69.44
LogP3.4
Topological polar surface area26.3

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.