Capsaicin

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

What is the Capsaicin?

The molecule Capsaicin presents a molecular formula of C₁₈H₂₇NO₃ and its IUPAC name is (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide.

Capsaicin is the molecule responsible for the spicy heat in chili peppers. It is a natural product derived from the pepper plant, and its chemical structure was first determined in 1919. Capsaicin is an irritant to mammals, including humans, and produces a burning sensation upon contact. This sensation is caused by the activation of heat-sensitive neurons in the skin..

Capsaicin is used in pepper spray as a self-defense weapon and in topical ointments to provide relief from pain. It is also being studied for its potential health benefits, including its ability to fight cancer and obesity..

The spiciness of capsaicin is measured in Scoville heat units (SHU). The hottest chili peppers, such as the Carolina Reaper, can have a capsaicin concentration of up to 16 million SHU. In comparison, bell peppers have a capsaicin concentration of zero SHU..

Capsaicin is insoluble in water but can be extracted from peppers using an organic solvent such as ethanol. It is also possible to synthesize capsaicin in the laboratory..

Capsaicin has a number of potential health benefits. It is an antioxidant and has anti-inflammatory properties. Capsaicin also has the ability to boost metabolism and promote weight loss..

Some studies have shown that capsaicin can kill cancer cells and shrink tumors. It is also being studied as a treatment for pain, arthritis, and psoriasis..

Capsaicin is generally considered safe, but it can cause side effects such as skin irritation, stomach upset, and diarrhea. It is important to use capsaicin products as directed and to wash your hands after contact..

3D structure

Cartesian coordinates

Geometry of Capsaicin 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.