(s)-2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid

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

What is the (s)-2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid?

The molecule (s)-2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid presents a molecular formula of C10H12O5 and its IUPAC name is (2S)-2-hydroxy-3-(2-methoxyphenoxy)propanoic acid.

2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid, also known as 2-hydroxy-3-methoxyphenoxypropanoic acid orHMPA, is a molecule with the chemical formula C9H10O4. It is a white solid that is insoluble in water..

HMPA is a derivative of phenoxyacetic acid, with the addition of a methoxy group at the 3-position. It is used as a precursor to herbicides and insecticides..

HMPA is synthesized by the reaction of 2-methoxyphenol and propanoic acid in the presence of a base, such as sodium hydroxide..

The herbicide glyphosate is produced by the reaction of HMPA with N,N′-dimethylformamide..

The insecticide fenamiphos is produced by the reaction of HMPA with N,N-dimethylphosphoramidic dichloride..

3D structure

Cartesian coordinates

Geometry of (s)-2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(s)-2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid MXVBBOLVTSAHEX-ZETCQYMHSA-N chemical compound 2D structure molecule svg
(s)-2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid

 

Molecule descriptors

 
IUPAC name(2S)-2-hydroxy-3-(2-methoxyphenoxy)propanoic acid
InChI codeInChI=1S/C10H12O5/c1-14-8-4-2-3-5-9(8)15-6-7(11)10(12)13/h2-5,7,11H,6H2,1H3,(H,12,13)/t7-/m0/s1
InChI KeyMXVBBOLVTSAHEX-ZETCQYMHSA-N
SMILESCOc1ccccc1OC[C@H](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.

  • (s)-2-Hydroxy-3-(2-methoxyphenoxy)propanoic acid
  • (s)-2-hydroxy-3-(2-methoxyphenoxy)propanoic acid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC6019312

Physico-Chemical properties

IUPAC name(2S)-2-hydroxy-3-(2-methoxyphenoxy)propanoic acid
Molecular formulaC10H12O5
Molecular weight212.199
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity51.97
LogP0.5
Topological polar surface area76.0

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.