Milbemycin A4

Base Information

• Chemical Name: Milbemycin A4
• CAS No.: 51596-11-3
• Deprecated CAS: 56197-02-5
• Molecular Formula: C₃₂H₄₆O₇
• Molecular Weight: 542.713
• UNII: 9BSH89E55Y
• DSSTox Substance ID: DTXSID4052760
• Nikkaji Number: J34.158D
• Wikidata: Q27119775
• Metabolomics Workbench ID: 56197
• ChEMBL ID: CHEMBL2272397
• Mol file: 51596-11-3.mol

Synonyms:5-hydroxymilbemycin beta7;CL 301,423;CL 301423;Cydectin;Milbeknock;milbemectin;milbemycin A3;milbemycin A4;milbemycin alpha1;milbemycin alpha10;milbemycin alpha11;milbemycin alpha13;milbemycin alpha14;milbemycin alpha15;milbemycin alpha2;milbemycin alpha3;milbemycin alpha4;milbemycin alpha5;milbemycin alpha6;milbemycin alpha7;milbemycin alpha8;milbemycin alpha9;milbemycin B;milbemycin beta1;milbemycin beta12;milbemycin beta2;milbemycin beta3;milbemycin D;milbemycins;mixture of milbemycins A3 and A4;moxidectin

Chemical Property of Milbemycin A4

Chemical Property:

• Melting Point: 212-215°
• Boiling Point: 732.9°Cat760mmHg
• PKA: 12.46±0.70(Predicted)
• Flash Point: 233.3°C
• PSA: 94.45000
• Density: 1.2g/cm³
• LogP: 4.92430
• Storage Temp.: 0-6°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 542.32435380
• Heavy Atom Count: 39
• Complexity: 1060

Purity/Quality:

98% ,99% , ^*data from raw suppliers

MilbemycinA4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(CCC2(O1)CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)C)C
• Isomeric SMILES: CC[C@@H]1[C@H](CC[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)\C)C
• Description: Milbemycin A4 is the prominent member of a complex family of macrocyclic lactones that contain a characteristic spiroketal group produced from the fermentation of soil bacterium S. hygroscopicus subsp. aureolacrimosus. As a compound that potentiates glutamate and GABA-gated chloride-channel opening, milbemycin 4 is used as a nematocide and insecticide.
• Uses: Milbemycins are a complex family of macrocyclic lactones containing a highly characteristic spiroketal group, produced by Streptomyces hydroscopicus subsp. aureolarcrimosus. Milbemycin A4 is the dominant member of a group of analogues containing a 25-ethyl substituent. Milbemycin A4 is a highly selective and potent nematocide and insecticide. Like the closely related avermectins, milbemycins are thought to act on chloride-gated ion channels. Acaricide. Milbemycin A4 is a macrolide compound that is a member of a complex family of macrocyclic lactones that contain structural group produced from the fermentation of soil bacterium S. hygroscopicus subsp. aureolacrimosus. Antibacterial and insecticide (1,2). It potentiates glutamate and GABA-gated chloride-channel opening. Used in the synthesis of Milbemycin A17 (3).

Technology Process of Milbemycin A4

There total 7 articles about Milbemycin A4 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:

5-oxo-5-deoxymilbemycin A4 (86691-97-6) → milbemycin A4 (51596-11-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; Yield given; -40 up to 0 deg C;

DOI:10.1016/0040-4039(94)80121-5

Reference yield:

C35H54O7Si (160035-93-8) → milbemycin A4 (51596-11-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / 1N HCl / methanol / Ambient temperature

2: Dess-Martin periodinane / CH₂Cl₂ / 0 °C

3: imidazole / CH₂Cl₂ / 0 °C

4: NaBH₄ / methanol / -40 up to 0 deg C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; Dess-Martin periodane; In methanol; dichloromethane;

DOI:10.1016/0040-4039(94)80121-5

Reference yield:

C35H54O7Si (160035-92-7) → milbemycin A4 (51596-11-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / 1.) LDA; 2.) AcOH / tetrahydrofuran / -78 °C / 1.) 10 min; 2.) 5 min

2: 94 percent / 1N HCl / methanol / Ambient temperature

3: Dess-Martin periodinane / CH₂Cl₂ / 0 °C

4: imidazole / CH₂Cl₂ / 0 °C

5: NaBH₄ / methanol / -40 up to 0 deg C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; Dess-Martin periodane; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0040-4039(94)80121-5

upstream raw materials:

5-oxo-5-deoxymilbemycin A₄

C₃₅H₅₄O₇Si

C₃₅H₅₄O₇Si

C₃₂H₄₄O₇

Downstream raw materials:

5-ketomilbemycin A₄ 5-oxime

5-O-methylmilbemycin A4