8,9-Z-Abamectin B1a

• CAT Number: R033143
• CAS Number: 113665-89-7
• Molecular Formula: C48H72O14
• Molecular Weight: 873.09
• Purity: ≥95%
• Synonyms: (8Z)-5-O-Demethylavermectin A1a; Spiro[11,15-methano-2H,13H,17H-furo[4,3,2-pq][2,6]benzodioxacyclooctadecin-13,2’-[2H]pyran] Avermectin A1a Deriv.
• Storage: -20°C
• IUPAC Name: (2R,3S,4'S,6S,8'R,10'E,13'S,14'E,16'E,20'R,21'R,24'S)-2-butan-2-yl-21',24'-dihydroxy-12'-[5-(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
• 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
• InChIKey: RRZXIRBKKLTSOM-NJRQVPCTSA-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

8,9-Z-Abamectin B1a (CAS 113665-89-7) is a photodegradation product of Avermectin B1a; a natural product derived from the soil actinomycete Streptomyces avermitilis. It is an antiparasitic agent that paralyzes nematodes without causing hypercontraction or flaccid paralysis.

Reference

1.Lofgren, C. S., and D. F. Williams. "Avermectin B1a: highly potent inhibitor of reproduction by queens of the red imported fire ant (Hymenoptera: Formicidae)." Journal of Economic Entomology 75.5 (1982): 798-803.
2.Kass, I. S., et al. "Avermectin B1a, a paralyzing anthelmintic that affects interneurons and inhibitory motoneurons in Ascaris." Proceedings of the National Academy of Sciences 77.10 (1980): 6211-6215.
3.Fritz, Lawrence C., Ching C. Wang, and Alfredo Gorio. "Avermectin B1a irreversibly blocks postsynaptic potentials at the lobster neuromuscular junction by reducing muscle membrane resistance." Proceedings of the National Academy of Sciences 76.4 (1979): 2062-2066.
4.Maynard, Michael S., et al. "Fate of the 8, 9-Z isomer of avermectin B1a in rats." Journal of Agricultural and Food Chemistry 37.6 (1989): 1487-1491.
5.Maynard, Michael S., and Heather D. Maynard. "HPLC assay for avermectin B1a and its two photoisomers using a photo diode array detector." Bulletin of environmental contamination and toxicology 43.4 (1989): 499-504.
6.Crouch, Louis S., et al. "Photodegradation of avermectin B1a thin films on glass." Journal of agricultural and food chemistry 39.7 (1991): 1310-1319.