Emamectin B1a

• CAT Number: R005250
• CAS Number: 121124-29-6
• Molecular Formula: C49H75NO13
• Molecular Weight: 886.133
• Purity: ≥95%
• Storage: -20°C
• InChI: InChI=1S/C49H75NO13/c1-12-26(2)44-29(5)18-19-48(63-44)24-35-21-34(62-48)17-16-28(4)43(27(3)14-13-15-33-25-56-46-42(51)30(6)20-36(47(52)59-35)49(33,46)53)60-40-23-38(55-11)45(32(8)58-40)61-39-22-37(54-10)41(50-9)31(7)57-39/h13-16,18-20,26-27,29,31-32,34-46,50-51,53H,12,17,21-25H2,1-11H3/b14-13+,28-16+,33-15+/t26-,27-,29-,31-,32-,34+,35-,36-,37-,38-,39-,40-,41+,42+,43-,44+,45-,46+,48+,49+/m0/s1
• InChIKey: CXEGAUYXQAKHKJ-COFQVFHOSA-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)NC)OC)OC)C)C

Emamectin B1a is a semi-synthetic 4/-epimethylamino analogue of avermectin B1a prepared by oxidation of the 4/-hydroxy moiety and reductive amination. The introduction of the methylamino group greatly enhances the insecticidal potency of the avermectin class. Emamectin B1a, as a benzoate salt, is the major component (>90%) of the commercial insecticide/acaricide, emamectin.Members of the avermectin/milbemycin class exert their insecticidal/anthelmintic effects by binding to glutamate-gated chloride channels expressed on nematode neurones and pharyngeal muscle cells.

Reference

Discovery of novel avermectins with unprecedented insecticidal activity. Mrozik H. et al. Experientia 1989, 45, 315.Synthesis of 4/-epi-amino-4/-deoxyavermectins B1. Cvetovich R.J. et al. J. Org. Chem. 1994, 59, 7704.