Fumaric acid

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

What is the Fumaric acid?

The molecule Fumaric acid presents a molecular formula of C4H4O4 and its IUPAC name is (E)-but-2-enedioic acid.

Fumaric acid is a carboxylic acid with the chemical formula HO2CCH=CHCO2H. It is an organic compound that is used as a food additive and is also a component of many industrial polymers. Fumaric acid is a white solid at room temperature and is soluble in water. It has a pungent, acidic taste and is used as a food acidulant. Fumaric acid belongs in nature as a component of many fruits and vegetables, such as strawberries, tomatoes, and apples. It is also a component of fumarates, which are salts or esters of fumaric acid..

Fumaric acid is used as a food additive because of its sour taste. It is used as an acidulant, flavor enhancer, and dough conditioner. It is also used as a preservative in some foods. Fumaric acid is a component of many industrial polymers, such as polyurethanes, resins, and adhesives. It is also used in the manufacture of alkyd resins, which are used in paints and coatings. Fumaric acid is used as a pH adjuster in cosmetics and personal care products. It is also used as a rust inhibitor in metal working fluids..

3D structure

Cartesian coordinates

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

2D drawing

 

Fumaric acid VZCYOOQTPOCHFL-OWOJBTEDSA-N chemical compound 2D structure molecule svg
Fumaric acid

 

Molecule descriptors

 
IUPAC name(E)-but-2-enedioic acid
InChI codeInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChI KeyVZCYOOQTPOCHFL-OWOJBTEDSA-N
SMILESC(=C/C(=O)O)\\C(=O)O

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 name(E)-but-2-enedioic acid
Molecular formulaC4H4O4
Molecular weight116.07
Melting point (ºC)287
Boiling point (ºC) -
Density (g/cm3)1.635
Molar refractivity
LogP-0.3
Topological polar surface area74.6

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.