4'-Hydroxy-3'-Methylacetophenone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 4'-Hydroxy-3'-Methylacetophenone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 4'-Hydroxy-3'-Methylacetophenone?

The molecule 4'-Hydroxy-3'-Methylacetophenone presents a molecular formula of C9H10O2 and its IUPAC name is 4'-hydroxy-3'-methylacetophenone.

4'-Hydroxy-3'-Methylacetophenone is a molecule with the molecular formula C8H9NO2. It is a white solid with a melting point of 101-102 °C. It is soluble in water, ethanol, and acetone..

This molecule is an acetophenone derivative with a hydroxy group at the 4' position and a methyl group at the 3' position. It is a member of the class of compounds known as substituted acetophenones..

4'-Hydroxy-3'-methylacetophenone is used as a starting material for the synthesis of various pharmaceuticals and fine chemicals..

The hydroxy group at the 4' position makes this molecule a good substrate for the enzyme CYP2D6. This enzyme is responsible for the metabolism of many drugs, including antidepressants, antipsychotics, and beta blockers..

The methyl group at the 3' position makes this molecule a good substrate for the enzyme CYP3A4. This enzyme is responsible for the metabolism of many drugs, including statins, calcium channel blockers, and immunosuppressants..

4'-Hydroxy-3'-methylacetophenone is also a good substrate for the enzyme CYP2C9. This enzyme is responsible for the metabolism of many drugs, including warfarin, phenytoin, and tolbutamide..

This molecule has a pKa of 9.96. This means that it is a weak acid and will dissociate in water to form the hydroxymethyl cation and the acetate anion..

The hydroxymethyl cation is a good nucleophile and will react with electrophiles. The acetate anion is a good leaving group and will be displaced by nucleophiles..

4'-Hydroxy-3'-methylacetophenone is a good substrate for the enzyme CYP2D6. This enzyme is responsible for the metabolism of many drugs, including antidepressants, antipsychotics, and beta blockers..

The methyl group at the 3' position makes this molecule a good substrate for the enzyme CYP3A4. This enzyme is responsible for the metabolism of many drugs, including statins, calcium channel blockers, and immunosuppressants..

4'-Hydroxy-3'-methylacetophenone is also a good substrate for the enzyme CYP2C9. This enzyme is responsible for the metabolism of many drugs, including warfarin, phenytoin, and tolbutamide..

This molecule has a pKa of 9.96. This means that it is a weak acid and will dissociate in water to form the hydroxymethyl cation and the acetate anion..

The hydroxymethyl cation is a good nucleophile and will react with electrophiles. The acetate anion is a good leaving group and will be displaced by nucleophiles..

3D structure

Cartesian coordinates

Geometry of 4'-Hydroxy-3'-Methylacetophenone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

4'-Hydroxy-3'-Methylacetophenone LXBHHIZIQVZGFN-UHFFFAOYSA-N chemical compound 2D structure molecule svg
4'-Hydroxy-3'-Methylacetophenone

 

Molecule descriptors

 
IUPAC name4'-hydroxy-3'-methylacetophenone
InChI codeInChI=1S/C7H6FNO2/c1-5-4-6(8)2-3-7(5)9(10)11/h2-4H,1H3
InChI KeyLXBHHIZIQVZGFN-UHFFFAOYSA-N
SMILESc1(cc(c(cc1)O)C)C(=O)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 name4'-hydroxy-3'-methylacetophenone
Molecular formulaC9H10O2
Molecular weight150.175
Melting point (ºC)108
Boiling point (ºC)-
Density (g/cm3)-
Molar refractivity43.63
LogP1.9
Topological polar surface area45.8

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.