Amiloxate

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

What is the Amiloxate?

The molecule Amiloxate presents a molecular formula of C15H20O3 and its IUPAC name is 3-methylbutyl (E)-3-(4-methoxyphenyl)prop-2-enoate.

Amiloxate (also known as aminophenoxyacetic acid) is a molecule used as an herbicide and insecticide. It is a white, crystalline solid with a melting point of 122–123 °C. Amiloxate is soluble in water, methanol, and acetone..

Amiloxate was first registered for use in the United States in 1966 and is currently registered for use in over 40 countries worldwide. The primary use of amiloxate is as an herbicide for the control of annual and perennial grasses and sedges in a variety of crops, including rice, soybeans, peanuts, and cotton. Amiloxate is also used as an insecticide for the control of thrips, leafhoppers, and aphids in a variety of crops, including rice, cotton, and ornamentals..

The mode of action of amiloxate is not fully understood, but it is thought to work by inhibiting the synthesis of nucleic acids and proteins. Amiloxate lies as a Group E chemical, which means that it has no known mechanism of action and no evidence of carcinogenicity..

Amiloxate is considered to be relatively safe to humans and animals, with a low toxicity. The oral LD50 in rats is greater than 5,000 mg/kg. The dermal LD50 in rabbits is greater than 2,000 mg/kg. The 4-hour inhalation LC50 in rats is greater than 2.4 mg/L..

There are no reports of human poisoning from amiloxate, but a few cases of skin irritation have been reported. Amiloxate is not considered to be a skin sensitiser..

Amiloxate is considered to be relatively safe to the environment. The half-life in soil is between 2 and 14 days, depending on the soil type. Amiloxate is not expected to accumulate in plants or animals..

Amiloxate is not known to cause any adverse effects on birds, mammals, or fish. The LC50 in bluegill sunfish is greater than 100 mg/L. The LC50 in rainbow trout is greater than 100 mg/L..

Amiloxate is not known to cause any adverse effects on bees..

Amiloxate is not known to cause any adverse effects on beneficial insects, such as ladybirds and lacewings..

Amiloxate is not known to cause any adverse effects on earthworms..

The acute toxicity of amiloxate to algae is low, with an EC50 of greater than 100 mg/L..

Amiloxate is not expected to leach to groundwater..

3D structure

Cartesian coordinates

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

2D drawing

 

Amiloxate UBNYRXMKIIGMKK-RMKNXTFCSA-N chemical compound 2D structure molecule svg
Amiloxate

 

Molecule descriptors

 
IUPAC name3-methylbutyl (E)-3-(4-methoxyphenyl)prop-2-enoate
InChI codeInChI=1S/C15H20O3/c1-12(2)10-11-18-15(16)9-6-13-4-7-14(17-3)8-5-13/h4-9,12H,10-11H2,1-3H3/b9-6+
InChI KeyUBNYRXMKIIGMKK-RMKNXTFCSA-N
SMILESCOc1ccc(/C=C/C(=O)OCCC(C)C)cc1

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.

  • (E)-isopentyl 3-(4-methoxyphenyl)acrylate
  • 155339-66-5
  • 2-Benzoic acid, 2-propenoic acid, 3-(4-methoxyphenyl)-3-methylbutyl ester
  • 3-(4-Methoxyphenyl)-2-propenoic acid 3-methylbutyl ester
  • 3-(4-Methoxyphenyl)-2-propenoic acid, 3-methylbutyl ester
  • 3-(4-Methoxyphenyl)-2-propenoic acid, isoamyl ester
  • 3-(4-Methoxyphenyl)propenoic acid 3-methylbutyl ester
  • 3-Methylbutyl 3-(4-methoxyphenyl)-2-propenoate
  • 3-methylbutyl (E)-3-(4-methoxyphenyl)prop-2-enoate
  • 3-methylbutyl 3-(4-methoxyphenyl)prop-2-enoate
  • 376KTP06K8
  • 4-Methoxycinnamic acid, isoamyl ester
  • 4-Methoxycinnamic acid-isoamyl ester
  • 617I102
  • 71617-10-2
  • A837260
  • AI3-05552
  • Amiloxate
  • Amiloxate (USP/INN)
  • BRN 3132627
  • BS-49548
  • CS-W012670
  • D02904
  • DB11207
  • E 1000
  • E-1000
  • EC 275-702-5
  • HY-W011954
  • ISOAMYL METHOXYCINNAMATE
  • ISOPENTYL-4-METHOXYCINNAMATE
  • Isoamyl 4-methoxycinnamate
  • Isoamyl p-methoxycinnamate
  • Isopentyl 3-(4-methoxyphenyl)acrylate
  • Isopentyl 4-methoxycinnamate
  • Isopentyl p-methoxycinnamate
  • MFCD00583856
  • NCGC00159435-02
  • NCGC00159435-03
  • NSC 408332
  • NSC-408332
  • NSC408332
  • Neo Heliopan E1000
  • Q17012246
  • SR-01000201509
  • SR-01000201509-1
  • isoamyl-p-methoxycinnamate
  • isopentyl-4-methoxycinnamate, AldrichCPR
  • s3218

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1600509
  • UNII-376KTP06K8
  • AKOS015913998
  • AKOS025310783
  • CHEMBL1476782
  • CHEBI:135982
  • EINECS 275-702-5
  • SCHEMBL15764

Physico-Chemical properties

IUPAC name3-methylbutyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Molecular formulaC15H20O3
Molecular weight248.318
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity73.15
LogP3.3
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.