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Abamectin

Catalog Number: BT-257972

CAS Number: 71751-41-2

Molecular Formula: C95H142O28

Molecular Weight: 873.1 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Abamectin is a natural product derived from the soil bacterium Streptomyces avermitilis. It belongs to the class of macrocyclic lactones and is widely used as an insecticide and acaricide in agriculture. Abamectin has also shown potential in medical and environmental research due to its unique chemical structure and biological activity.

Properties

CAS Number

71751-41-2

Product Name

Abamectin

IUPAC Name

(1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-butan-2-yl-21',24'-dihydroxy-12'-[(4S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one

Molecular Formula

C95H142O28

Molecular Weight

873.1 g/mol

InChI

InChI=1S/C48H72O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25?,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39?,40+,41-,42-,43+,44?,45+,47+,48+/m0/s1

InChI Key

IBSREHMXUMOFBB-CVSKBELMSA-N

SMILES

CCC(C)C1C(C=CC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)C

Solubility

Soluble in DMSO; 0.007-0.01 mg l-1 (20 °C)

Synonyms

Abamectin, Affirm, Agri-Mek, Agrimek, Avid, Avid EC, Avomec, EPA Pesticide Chemical Code 122804, HSDB 6941, MK 0936, MK 936, Vertimec, Zephyr

Canonical SMILES

CCC(C)C1C(C=CC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)C.CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)O)OC)OC)C)OC7(C4)C=CC(C(O7)C(C)C)C)O

Isomeric SMILES

CCC(C)[C@@H]1[C@H](C=C[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)\C)C.C[C@H]1/C=C/C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]4C[C@@H](C/C=C(/[C@H]1O[C@H]5C[C@@H]([C@H]([C@@H](O5)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O)OC)OC)\C)O[C@]7(C4)C=C[C@@H]([C@H](O7)C(C)C)C)O

Method of Synthesis or Extraction

Abamectin is commonly synthesized through fermentation of S. avermitilis. The yield and efficiency of this method depend on various factors such as the strain of bacteria, fermentation conditions, and downstream processing. Environmental and safety considerations are also important in the production of abamectin, as the use of antibiotics and other chemicals in the fermentation process can lead to the development of antibiotic-resistant bacteria and environmental pollution.

Chemical Structure and Biological Activity

Abamectin consists of two major components, avermectin B1a and B1b, which differ only in the presence of a single methyl group. The mechanism of action of abamectin involves binding to glutamate-gated chloride channels in the nervous system of insects and mites, leading to paralysis and death. Abamectin has also been shown to have activity against certain nematodes and other parasites.

Biological Effects

Abamectin has been found to have a range of effects on cell function and signal transduction, including inhibition of neurotransmitter release and modulation of ion channels. Potential therapeutic effects of abamectin include treatment of parasitic infections and neurological disorders. However, abamectin can also have toxic effects on non-target organisms, including mammals and aquatic life.

Applications

In medical research, abamectin has been studied for its potential role in drug development, particularly in the treatment of parasitic infections and neurological disorders. Clinical trials have shown promising results, but further research is needed to determine the safety and efficacy of abamectin in humans. In environmental research, abamectin has been used to manage pest populations and reduce the impact of pollution on ecosystems. However, the use of abamectin can also have unintended consequences, such as the development of resistance in target organisms and harm to non-target species. In industrial research, abamectin has been used to improve product quality and efficiency, but health and safety considerations must be taken into account.

Future Perspectives and Challenges

Current limitations in the use and study of abamectin include the development of resistance in target organisms, potential harm to non-target species, and the need for further research to determine the safety and efficacy of abamectin in humans. Possible solutions and improvements include the development of new formulations and delivery methods, as well as the use of integrated pest management strategies. Future trends and prospects in the application of abamectin in scientific research include the development of new drugs and therapies, as well as the continued exploration of its potential in environmental and industrial applications.
In conclusion, abamectin is a unique natural product with a range of potential applications in medical, environmental, and industrial research. However, careful consideration must be given to its safety and efficacy, as well as its potential impact on non-target organisms and the environment. Further research is needed to fully understand the potential benefits and challenges of abamectin in scientific research.

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