Avermectin B2a

Avermectin B2a

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Category Antibiotics
Catalog number BBF-00230
CAS 65195-57-5
Molecular Weight 891.09
Molecular Formula C48H74O15

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Description

Avermectin B2a is produced by the strain of Streptomyces avermitilis. It stimulates nerve cells to release Y-aminobutyric acid (GABA), which blocks the transmission of signals from the central nervous system to the motor nerve. It is not resistant to bacteria and fungi, but has strong activity to nematode parasites such as ancylostoma and Pteria, as well as insects such as flies. Abamectin B1a has the highest activity. Ivermectin obtained by catalytic hydrogenation contains 22 23- dihydroabamectin B1a (above 80%) and 22 23 dioxabamectin B1b (below 20%). Less active than B1a but less toxic. Used as repellent (subcutaneous or oral) for cattle, sheep and pigs, it is also effective against human filariasis.

Specification

Synonyms SCHEMBL1681286
IUPAC Name (1R,4S,4'S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-butan-2-yl-4',21,24-trihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
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)O)C
InChI InChI=1S/C48H74O15/c1-11-24(2)43-28(6)35(49)22-47(63-43)21-33-18-32(62-47)16-15-26(4)42(25(3)13-12-14-31-23-56-45-40(50)27(5)17-34(46(52)59-33)48(31,45)53)60-39-20-37(55-10)44(30(8)58-39)61-38-19-36(54-9)41(51)29(7)57-38/h12-15,17,24-25,28-30,32-45,49-51,53H,11,16,18-23H2,1-10H3/b13-12+,26-15+,31-14+/t24?,25-,28-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47-,48+/m0/s1
InChI Key CWGATOJEFAKFBK-QJDTYEMPSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum parasites

Reference Reading

1. High Value Utilization of an Avermectin Fermentation Byproduct: Novel B2a Derivatives as Pesticide Candidates
Qingbo Xu, Jinming Li, Wenxiu Guo, Juncheng Xiang, Liqi Zhou, Jianjun Zhang J Agric Food Chem. 2022 Jun 1;70(21):6377-6384. doi: 10.1021/acs.jafc.2c01035. Epub 2022 May 18.
In an effort to develop novel molecules with suitable insecticidal activities, 23,24-alkene-avermectin B2a derivatives have been synthesized via a one-pot multistep reaction using avermectin B2a, a byproduct of avermectin fermentation, as a starting material. All products and intermediates were characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometry. Bioassay results showed that the LC50 values of compounds 4 and 9 against Meloidogyne incognita were 0.63 and 0.50 mg/L, respectively, similar to that of avermectin (0.46 mg/L). Importantly, the LC50 values of compound 9 against Tetranychus cinnabarinus and Mythimna separate were 0.0067 and 0.047 mg/L, respectively, superior to that of avermectin. Through field experiments, it could be found that spraying 0.25% water-dispersible granules of compound 9 345 g ha-1 could effectively control M. incognita outbreaks, with an efficacy of 84.9%. Combined with toxicity experiments, it could be further inferred that compound 9 may be useful as a low-toxicity pesticide. In summary, we efficiently synthesized a new B2a derivative as a potential pesticide and offered an important way for improving the utilization efficiency of avermectin fermentation products. In doing so, the environmental pollution associated with fermentation byproducts may be greatly reduced, potentially enabling a sustainable avermectin fermentation process.
2. Synthesis and insecticidal activities of 5-deoxyavermectin B2a oxime ester derivatives
Guoshao Sun, Jingjing Zhang, Shuhui Jin, Jianjun Zhang RSC Adv. 2018 Jan 22;8(7):3774-3781. doi: 10.1039/c7ra13258a. eCollection 2018 Jan 16.
Three series of avermectin B2a oxime ester derivatives were synthesized using avermectin B2a as starting material. All of the compounds were characterized by 1H NMR, 13C NMR, and HRMS. Bioassay results indicated that some of the derivatives (8b, 8c, 8d, 8f, 11k, 11l, 14c, 14j) showed potent insecticidal activities against Myzus persicae, Caenorhabditis elegans, or Tetranychus cinnabarinus. As shown by initial insecticidal activity data, compound 8d showed excellent activities (>90%) against M. persicae and C. elegans, which were more potent than that of avermectin B2a. Compound 8d might be a lead compound for designing new avermectin B2a derivatives.
3. Organocatalytic Site-Selective Acylation of Avermectin B2a, a Unique Endectocidal Drug
Takeshi Yamada, Koh Suzuki, Tomoyasu Hirose, Takumi Furuta, Yoshihiro Ueda, Takeo Kawabata, Satoshi Ōmura, Toshiaki Sunazuka Chem Pharm Bull (Tokyo). 2016 Jul 1;64(7):856-64. doi: 10.1248/cpb.c16-00205. Epub 2016 Apr 12.
The organocatalytic site-selective monoacylation of avermectin B2a, an insecticidal and anti-parasitic drug, was accomplished. Although an acetylation of avermectin B2a using a 4-dimethylaminopyridine (DMAP) as a catalyst gave poor site-selectivity, use of our organocatalyst increased site-selectivity of the acylation at the C-5-OH as well as the yield of monoacetate. This catalyst was also effective in other acylations. Interestingly, trihaloacetylation under same conditions gave poor site-selectivity. However, the use of an enantiomer of our organocatalyst provided the C-4″-O-trihaloacetyl avermectin B2a with excellent site-selectivity. These results indicate that the site-selective acylation of avermectin B2a can be controlled by the combination of a suitable organocatalyst and an acid anhydride.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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