(-)-trans-Permethrin

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

What is the (-)-trans-Permethrin?

The molecule (-)-trans-Permethrin presents a molecular formula of C21H20Cl2O3 and its IUPAC name is (3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate.

Permethrin is a molecule in the class of organic compounds known as pyrethroids. It is a synthetic compound that acts as a potent insecticide and acaricide. It is used in agriculture to control a wide variety of pests, including mites, aphids, thrips, and whiteflies. It is also used in public health to control mosquito populations..

Permethrin is a highly effective insecticide because it acts on the nervous system of insects. It is a neurotoxin that binds to the voltage-gated sodium channels in the nerve cell membranes. This prevents the channels from opening and closing, which disrupts the flow of sodium ions and prevents the nerves from firing. This leads to paralysis and death of the insect..

Permethrin is relatively safe to humans and other mammals because it does not bind to the voltage-gated sodium channels in our nerve cell membranes. However, it is highly toxic to fish and other aquatic organisms. It is also toxic to bees and other pollinating insects..

Permethrin is a persistent organic pollutant and will remain in the environment for many years. It is important to use it only when necessary and to follow all label instructions carefully to minimize its impact on the environment..

3D structure

Cartesian coordinates

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

2D drawing

 

(-)-trans-Permethrin RLLPVAHGXHCWKJ-MJGOQNOKSA-N chemical compound 2D structure molecule svg
(-)-trans-Permethrin

 

Molecule descriptors

 
IUPAC name(3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
InChI codeInChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19+/m1/s1
InChI KeyRLLPVAHGXHCWKJ-MJGOQNOKSA-N
SMILESCC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCc1cccc(Oc2ccccc2)c1

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.

  • (-)-TRANS-PERMETHRIN
  • (-)-trans-Permethrin
  • (1R)-trans-Permethrin
  • (?)-trans-Permethrin
  • (SR)-cis-Permethrin
  • 1S,TRANS-PERMETHRIN
  • 1S-trans-Permethrin
  • 3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate #
  • 3-phenoxybenzyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
  • 54774-47-9
  • BIDD:GT0131
  • C19864
  • CYCLOPROPANECARBOXYLIC ACID, 3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL-, (3-PHENOXYPHENYL)METHYL ESTER, (1S,3R)-
  • Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1S,3R)
  • Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1S-trans)-
  • Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester, (1R-trans)-
  • NCGC00159390-03
  • PERMETHRIN, TRANS-(-)-
  • Permethrin trans
  • Permethrin, (-)-trans-
  • Q27131987
  • WTX0TDW4JB
  • trans-(-)-permethrin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2032615
  • UNII-WTX0TDW4JB
  • DTXSID7058254
  • CHEMBL600685
  • CHEBI:62523
  • SCHEMBL121233

Physico-Chemical properties

IUPAC name(3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Molecular formulaC21H20Cl2O3
Molecular weight391.288
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity104.41
LogP6.1
Topological polar surface area35.5

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.