(1R)-trans-Phenothrin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (1R)-trans-Phenothrin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (1R)-trans-Phenothrin?

The molecule (1R)-trans-Phenothrin presents a molecular formula of C23H26O3 and its IUPAC name is (3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate.

Phenothrin is an insecticide that is used to kill a variety of pests, including mosquitoes, flies, and ticks. It is a synthetic version of a naturally occurring compound called pyrethrin, which belongs in the flower heads of certain chrysanthemum plants. Phenothrin works by causing muscle spasms and paralysis in insects, ultimately leading to their death..

Phenothrin exists in a variety of formulations, including aerosolable sprays, foggers, and traps. It can be used both indoors and outdoors, and is considered to be relatively safe for humans and animals when used as directed. However, phenothrin can be toxic if inhaled or ingested in large quantities, and should be used with caution in households with children or pets..

3D structure

Cartesian coordinates

Geometry of (1R)-trans-Phenothrin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(1R)-trans-Phenothrin SBNFWQZLDJGRLK-RTWAWAEBSA-N chemical compound 2D structure molecule svg
(1R)-trans-Phenothrin

 

Molecule descriptors

 
IUPAC name(3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
InChI codeInChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3/t20-,21+/m1/s1
InChI KeySBNFWQZLDJGRLK-RTWAWAEBSA-N
SMILESCC(C)=C[C@@H]1[C@@H](C(=O)OCc2cccc(Oc3ccccc3)c2)C1(C)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.

  • (-)-trans-Phenothrin
  • (1R)-trans-Phenothrin
  • (1R,3R)-3-Phenoxybenzyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
  • (1R-TRANS)-BIOPHENOTHRIN
  • (3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
  • (3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
  • 046D855
  • 1R,3R-PHENOTHRIN
  • 1R-trans-Phenothrin
  • 26046-85-5
  • 3-phenoxybenzyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
  • 51186-86-8
  • 6JX527V7HJ
  • 74430-94-7
  • A818151
  • Biophenothrin
  • CS-0119677
  • CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)-, (3-PHENOXYPHENYL)METHYL ESTER, (1R,3R)-
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (3-phenoxyphenyl)methyl ester, (1R,3R)-
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (3-phenoxyphenyl)methyl?ester, (1R,3R)-
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (3-phenoxyphenyl)methyl ester, (1R-trans)-
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (3-phenoxyphenyl)methyl ester, trans-(+-)-
  • D-Phenothrin
  • HY-B1072A
  • PHENOTHRIN, TRANS-(-)-
  • Q27119853
  • d-trans-Phenothrin
  • delta-phenothrin
  • m-Phenoxybenzyl (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
  • phenothrin [(1R)-trans- isomer]
  • trans-(-)-phenothrin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC608024
  • UNII-6JX527V7HJ
  • AKOS015895466
  • DTXSID1058347
  • CHEBI:39405
  • EINECS 247-431-2
  • SCHEMBL8649333

Physico-Chemical properties

IUPAC name(3-phenoxyphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
Molecular formulaC23H26O3
Molecular weight350.451
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity104.43
LogP5.8
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.