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CAS 220119-16-4

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Avermectin A1a,25-cyclohexyl-5-demethoxy-25-de(1-methylpropyl)-22,23-dihydro-5-oxo- (9CI)

Description:
Avermectin A1a, also known by its chemical name 25-cyclohexyl-5-demethoxy-25-de(1-methylpropyl)-22,23-dihydro-5-oxo-, is a member of the avermectin family, which are macrocyclic lactones derived from the fermentation of the bacterium Streptomyces avermitilis. This compound exhibits potent anthelmintic and insecticidal properties, making it valuable in agricultural and veterinary applications. Avermectins function by binding to glutamate-gated chloride channels, leading to paralysis and death of susceptible parasites and insects. The structure of Avermectin A1a includes a complex macrocyclic ring system, which contributes to its biological activity. It is characterized by a high degree of lipophilicity, which enhances its ability to penetrate biological membranes. The compound is typically administered in formulations designed for targeted delivery, ensuring efficacy while minimizing environmental impact. Safety profiles indicate that while effective against pests, avermectins must be used judiciously to avoid toxicity in non-target organisms, including humans and beneficial insects.
Formula:C50H74O14
InChI:InChI=1S/C50H74O14/c1-27-13-12-16-34-26-57-47-42(51)30(4)21-37(50(34,47)54)48(53)60-36-22-35(63-49(25-36)20-19-29(3)45(64-49)33-14-10-9-11-15-33)18-17-28(2)44(27)61-41-24-39(56-8)46(32(6)59-41)62-40-23-38(55-7)43(52)31(5)58-40/h12-13,16-17,21,27,29,31-33,35-41,43-47,52,54H,9-11,14-15,18-20,22-26H2,1-8H3/b13-12+,28-17+,34-16+/t27-,29-,31-,32-,35+,36-,37-,38-,39-,40-,41-,43-,44-,45-,46-,47+,49+,50+/m0/s1
InChI key:InChIKey=JCXGGTZYZDLMDY-QYEATPFCSA-N
SMILES:O[C@]/12[C@@]3(OC\C1=C/C=C/[C@H](C)[C@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)\C(\C)=C\C[C@@]6(C[C@](OC(=O)[C@@]2(C=C(C)C3=O)[H])(C[C@@]7(O[C@@]([C@@H](C)CC7)(C8CCCCC8)[H])O6)[H])[H])[H]
Synonyms:
  • (25S)-Cyclohexyl-25-De(Sec-Butyl)- 5-Demethoxy-5-Oxo-22,23-Dihydroavermectin A1A
  • Avermectin A<sub>1a</sub>, 25-cyclohexyl-5-demethoxy-25-de(1-methylpropyl)-22,23-dihydro-5-oxo-
  • Avermectin A1a, 25-cyclohexyl-5-demethoxy-25-de(1-methylpropyl)-22,23-dihydro-5-oxo-
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  • 25-Cyclohexyl-5-demethoxy-25-de(1-methylpropyl)-22,23-dihydro-5-oxo-avermectin A1a
    TRC
    + Info

    25-Cyclohexyl-5-demethoxy-25-de(1-methylpropyl)-22,23-dihydro-5-oxo-avermectin A1a

    Controlled Product
    CAS:

    Applications 25-Cyclohexyl-5-demethoxy-25-de(1-methylpropyl)-22,23-dihydro-5-oxo-avermectin A1a is an intermediate in synthesizing 4'-O-2,6-Dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl Selamectin (D440100), which s an impurity of Selamectin (S247990), a topical parasiticide. Selamectin (S247990) is also used as a veterinary antihelminithic agent on animals.
    References Eshar, D., et al.: J. Am. Veterin. Med. Association., 241, 1056 (2012); Geis-Asteggiante, L., et al.: J. Chromatograph., 1258, 43 (2012);

    Formula:C50H74O14
    Color and Shape:Neat
    Molecular weight:899.11

    Ref: TR-C988133

    5mg
    175.00€
    50mg
    1,121.00€
    2500µg
    120.00€