Doramectin synthetic

Base Information

• Chemical Name: Doramectin synthetic
• CAS No.: 117704-25-3
• Molecular Formula: C50H74O14
• Molecular Weight: 899.129
• Hs Code.: 29419090
• European Community (EC) Number: 601-490-4
• Metabolomics Workbench ID: 144383
• NCI Thesaurus Code: C81559
• Wikipedia: Doramectin
• Mol file: 117704-25-3.mol

Synonyms:25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)avermectin A1a;avermectin A1a, 25-cyclohexyl-5-o-demethyl-25-de(1-methylpropyl)-;Dectomax;doramectin;L-701023;L701023;UK-67,994;UK-67994

Chemical Property of Doramectin synthetic

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 116-119 °C
• Refractive Index: 1.579
• Boiling Point: 967.4 °C at 760 mmHg
• PKA: 12.42±0.70(Predicted)
• Flash Point: 274.4 °C
• PSA: 170.06000
• Density: 1.25 g/cm³
• LogP: 5.91160
• Storage Temp.: 0-6°C
• Solubility.: methanol: soluble
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 898.50785703
• Heavy Atom Count: 64
• Complexity: 1790

Purity/Quality:

99%min ^*data from raw suppliers

Doramectin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N, Xi
• Hazard Codes: T,N,Xi
• Statements: 25-50/53-36/37/38
• Safety Statements: 33-45-60-61-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)O)OC)OC)C)OC7(C4)C=CC(C(O7)C8CCCCC8)C)O
• Isomeric SMILES: C[C@H]1/C=C/C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]4CC(C/C=C(/[C@H]1O[C@@H]5C[C@@H]([C@H]([C@@H](O5)C)O[C@@H]6C[C@@H]([C@H]([C@@H](O6)C)O)OC)OC)\C)O[C@]7(C4)C=C[C@@H]([C@H](O7)C8CCCCC8)C)O
• Description: Doramectin is a novel avermectin with a cyclohexyl substituent on the previously inaccessible C-25 position of the molecule; the substitution was facilitated by mutational biosynthesis. The discovery of doramectin involved feeding carboxylic acids or their precursors to a fermentation of Streptomyces avermitilis that lacked branched-chain 2-oxo acid dehydrogenase activity, and then screening the resultant fermentation products for anthelmintic and ectoparasiticidal activity (89). Two dosage forms of doramectin have been developed for use as an endectocide on cattle, an injectable formulation for subcutaneous administration and a pouron formulation. An injectable formulation is also approved for use on pigs.
• Uses: antibacterial Doramectin is a biosynthetic avermectin derived from a mutant strain of Streptomyces avermitilis, supplemented with a cyclohexylcaboxylic acid starting unit. Doramectin was developed as an anthelmintic for internal parasite control. The presence of the cyclohexyl group replacing the sec-butyl moiety affords greater hydrophobicity and longer biological half-life compared to avermectin. Like the other milbemycin/avermectins, it selectively binds to parasite glutamate-gated chloride ion channels and disrupts neurotransmission leading to paralysis and death of the parasite. A mutational biosynthetic antiparasitic antibiotic. Mutational biosynthetic antiparasitic antibiotic structurally related to the avermectins

Technology Process of Doramectin synthetic

There total 1 articles about Doramectin synthetic which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.6%

→ doramectin (117704-25-3)

Guidance literature:

Reference yield: 77.0%

doramectin (117704-25-3) + trifluoroacetic anhydride (407-25-0) → C52H69F3O13

Guidance literature:

With triethylamine; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/jf00041a034

Reference yield: 72.5%

doramectin (117704-25-3) → 5-ketodoramectin

Guidance literature:

With manganese(IV) oxide; In diethyl ether; for 18h; Ambient temperature;

DOI:10.1021/jf00041a034

Downstream raw materials:

[3H]-Selamectin

doramectin

Refernces