A naturally-occurring insecticide
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Spinosyn A

Item No. 16528

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-2-[(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-13-[[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]oxy]-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-14-methyl-1H-as-indaceno[3,2-d]oxacyclododecin-7,15-dione
CAS Number
131929-60-7
Synonyms
  • A-83543A
  • Lepicidin A
Molecular Formula
C41H65NO10
Formula Weight
732.0
Purity
≥99%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CN(C)[C@H]1CC[C@@](O[C@H]([C@@H](C)C2=O)CCC[C@H](CC)OC(C[C@]3([H])C2=C[C@]4([H])[C@@]3([H])C=C[C@@]5([H])[C@@]4([H])C[C@H](O[C@]6([H])O[C@@H](C)[C@H](OC)[C@@H](OC)[C@H]6OC)C5)=O)([H])O[C@@H]1C
InChi Code
InChI=1S/C41H65NO10/c1-10-26-12-11-13-34(52-36-17-16-33(42(5)6)23(3)48-36)22(2)37(44)32-20-30-28(31(32)21-35(43)50-26)15-14-25-18-27(19-29(25)30)51-41-40(47-9)39(46-8)38(45-7)24(4)49-41/h14-15,20,22-31,33-34,36,38-41H,10-13,16-19,21H2,1-9H3/t22-,23-,24+,25-,26+,27-,28-,29-,30-,31+,33+,34+,36+,38+,39-,40-,41+/m1/s1
InChi Key
SRJQTHAZUNRMPR-UYQKXTDMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Spinosyn A is a naturally-occurring macrocyclic lactone that is a potent insecticide.1,2 It acts as an agonist of insect nicotinic acetylcholinesterase receptors (nAChRs), which differ both structurally and functionally from nAChRs in vertebrates.3 As a result, it has low affinity for vertebrate nAChRs and has limited adverse effects in those animals.3,4 Spinosyn A is produced naturally by the fermentation of the bacterium S. spinosa and its chemical synthesis has been described.5 Formulations containing spinosyn A have been used in the control of insects in agriculture.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Creemer, L.C., Kirst, H.A., Paschal, J.W., et al. Synthesis and insecticidal activity of spinosyn analogs functionally altered at the 2'-,3'- and 4'-positions of the rhamnose moiety. J. Antibiot. (Tokyo) 53(2), 171-178 (2000).

    2. Duke, S.O., Cantrell, C.L., Meepagala, K.M., et al. Natural toxins for use in pest management. Toxins (Basel) 2(8), 1943-1962 (2010).

    3. Vo, D.T., Hsu, W.H., Abu-Basha, E.A., et al. Insect nicotinic acetylcholine receptor agonists as flea adulticides in small animals. J. Vet. Pharmacol. Ther. 33(4), 315-322 (2010).

    4. Amaral, T.S., Carvalho, T.F., Silva, M.C., et al. Short-term effects of a spinosyn’s family insecticide on energy metabolism and liver morphology in frugivorous bats Artibeus lituratus (Olfers, 1818). Braz. J. Biol. 72(2), 299-304 (2012).

    5. Mergott, D.J., Frank, S.A., and Roush, R.W. Total synthesis of (−)-spinosyn A. Proc. Natl. Acad. Sci. USA 101(33), 11955-11959 (2004).