Spinetoram L

Base Information

• Chemical Name: Spinetoram L
• CAS No.: 187166-15-0
• Molecular Formula: C43H69NO10
• Molecular Weight: 760.0
• UNII: 2Y6X4QH84Q
• DSSTox Substance ID: DTXSID2044341
• Nikkaji Number: J2.971.982I
• Wikidata: Q27255794
• Metabolomics Workbench ID: 143699

Synonyms:Spinetoram L;187166-15-0;spinosyn L, 3'-Ethoxy-;Spinetoram (minor component);Spinetoram (minor component) [ISO];UNII-2Y6X4QH84Q;2Y6X4QH84Q;(1S,2S,5R,7S,9S,10S,14R,15S,19S)-15-[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-7-[(2R,3R,4R,5S,6S)-4-ethoxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy-19-ethyl-4,14-dimethyl-20-oxatetracyclo[10.10.0.02,10.05,9]docosa-3,11-diene-13,21-dione;3/'-Ethoxy-spinosyn L;SCHEMBL678138;3'-O-ETHYL SPINOSYN L;DTXSID2044341;PD094756;Q27255794;1H-as-Indaceno[3,2-d]oxacyclododecin-7,15-dione, 2-[(6-deoxy-3-O-ethyl-2,4-di-O-methyl-.alpha.-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-4,14-dimethyl-, (2S,3aR,5aS,5bS,9S,13S,14R,16aS,16bS)-

Chemical Property of Spinetoram L

Chemical Property:

• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 759.49214740
• Heavy Atom Count: 54
• Complexity: 1350

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

3''-Ethoxy Spinosyn L ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1CCCC(C(C(=O)C2=CC3C4CC(CC4C(=CC3C2CC(=O)O1)C)OC5C(C(C(C(O5)C)OC)OCC)OC)C)OC6CCC(C(O6)C)N(C)C
• Isomeric SMILES: CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OCC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C
• General Description: Spinetoram L is a minor component of spinetoram, a semi-synthetic insecticide derived from fermentation, known for its broad-spectrum efficacy, environmental safety, and low toxicity to non-target organisms. While the study primarily focuses on spinetoram J and its analogues, it underscores the significance of sugar moiety modifications in enhancing insecticidal activity, though Spinetoram L itself was not directly evaluated in this research. The findings highlight the potential for optimizing spinosyn derivatives through structural adjustments to improve their pesticidal properties.

Refernces

Semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues

10.3762/bjoc.14.207

The study focuses on the semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues. Spinetoram, derived from fermentation, is a broad-spectrum insecticide that is environmentally friendly and non-toxic to animals and humans. The researchers improved the semi-synthesis process of spinetoram J by using 3-O-ethyl-2,4-di-O-methylrhamnose as both a reaction substrate and a protecting group, which simplified the synthesis steps and reduced costs. They also synthesized a range of D-forosamine replacement analogues and evaluated their insecticidal activities against Plutella xylostella larvae. Although the analogues did not match the potency of spinetoram, some showed only 20–40 times lower activity, with one analogue being nearly as active as spinosad. The findings suggest the potential for developing new insecticides by modifying sugar components in natural products and highlight the importance of the electrical properties of substituents in insecticidal activity.

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