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MedKoo Cat#: 413020 | Name: Milbemycin (free base)

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Milbemycin (free base) is a family of macrolide antibiotics with insecticidal & acaricidal activity; milbemectin is a mixture of milbemycins A3 and A4; moxidectin (CL 301,423) is milbemycin B.

Chemical Structure

Milbemycin (free base)
Milbemycin (free base)
CAS#51570-36-6 (free base)

Theoretical Analysis

MedKoo Cat#: 413020

Name: Milbemycin (free base)

CAS#: 51570-36-6 (free base)

Chemical Formula: C31H44O7

Exact Mass: 528.3087

Molecular Weight: 528.69

Elemental Analysis: C, 70.43; H, 8.39; O, 21.18

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
51570-36-6 (free base) 129496-10-2 (oxime) 114177-14-9 (A3 Oxime)
Synonym
Milbemycin (free base); CL301,423; CL-301,423; CL 301,423
IUPAC/Chemical Name
(6R,25R)-5-Demethoxy-28-deoxy-6,28-epoxy-25-ethyl-5-(hydroxyimino)milbemycin B
InChi Key
ZLBGSRMUSVULIE-GSMJGMFJSA-N
InChi Code
InChI=1S/C31H44O7/c1-18-7-6-8-23-17-35-28-27(32)21(4)14-26(31(23,28)34)29(33)36-25-15-24(10-9-19(2)13-18)38-30(16-25)12-11-20(3)22(5)37-30/h6-9,14,18,20,22,24-28,32,34H,10-13,15-17H2,1-5H3/b7-6+,19-9+,23-8+/t18-,20-,22+,24+,25-,26-,27+,28+,30-,31+/m0/s1
SMILES Code
C[C@@H]1C/C(C)=C/C[C@@H]2C[C@H](OC([C@@H]3C=C([C@H]([C@H]4OC/C([C@@]34O)=C\C=C\1)O)C)=O)C[C@@]5(O2)CC[C@@H]([C@H](O5)C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 528.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wang H, Cheng X, Liu Y, Li S, Zhang Y, Wang X, Xiang W. Improved milbemycin production by engineering two Cytochromes P450 in Streptomyces bingchenggensis. Appl Microbiol Biotechnol. 2020 Apr;104(7):2935-2946. doi: 10.1007/s00253-020-10410-8. Epub 2020 Feb 11. PMID: 32043186. 2: Gill JH, Lacey E. Avermectin/milbemycin resistance in trichostrongyloid nematodes. Int J Parasitol. 1998 Jun;28(6):863-77. doi: 10.1016/s0020-7519(98)00068-x. PMID: 9673866. 3: He H, Ye L, Li C, Wang H, Guo X, Wang X, Zhang Y, Xiang W. SbbR/SbbA, an Important ArpA/AfsA-Like System, Regulates Milbemycin Production in Streptomyces bingchenggensis. Front Microbiol. 2018 May 23;9:1064. doi: 10.3389/fmicb.2018.01064. PMID: 29875761; PMCID: PMC5974925. 4: Qi H, Zhang J, Hao ZK, Zhang SY, Li JS, Zhang LQ, Wang JD, Xiang WS. Two novel milbemycin derivatives from the genetically engineered strain Streptomyces avermitilis AVE-H39. J Antibiot (Tokyo). 2020 Sep;73(9):642-645. doi: 10.1038/s41429-020-0317-2. Epub 2020 May 29. PMID: 32472052. 5: Wang JD, Qi H, Zhang J, Li JS, Zhang SY, Hao ZK, Zhang LQ, Xiang WS. Two new 13-hydroxylated milbemycin metabolites from the genetically engineered strain Streptomyces avermitilis AVE-H39. J Asian Nat Prod Res. 2020 Aug 27:1-7. doi: 10.1080/10286020.2020.1803294. Epub ahead of print. PMID: 32851866. 6: Molento MB, Nielsen MK, Kaplan RM. Resistance to avermectin/milbemycin anthelmintics in equine cyathostomins - current situation. Vet Parasitol. 2012 Apr 19;185(1):16-24. doi: 10.1016/j.vetpar.2011.10.013. Epub 2011 Oct 18. PMID: 22047763. 7: Walker B, Izumikawa K, Tsai HF, Bennett JE. Milbemycin A4 oxime as a probe of azole transport in Candida glabrata. FEMS Yeast Res. 2014 Aug;14(5):755-61. doi: 10.1111/1567-1364.12164. Epub 2014 Jun 12. PMID: 24838041; PMCID: PMC4126866. 8: Zeltins A, Turks M, Skrastina D, Lugiņina J, Kalnciema I, Balke I, Bizdēna Ē, Skrivelis V. Synthesis and Immunological Evaluation of Virus-Like Particle- Milbemycin A₃/A₄ Conjugates. Antibiotics (Basel). 2017 Sep 11;6(3):18. doi: 10.3390/antibiotics6030018. PMID: 28892001; PMCID: PMC5617982. 9: Danaher M, Radeck W, Kolar L, Keegan J, Cerkvenik-Flajs V. Recent developments in the analysis of avermectin and milbemycin residues in food safety and the environment. Curr Pharm Biotechnol. 2012 May;13(6):936-51. doi: 10.2174/138920112800399068. PMID: 22039790. 10: Wolstenholme AJ, Rogers AT. Glutamate-gated chloride channels and the mode of action of the avermectin/milbemycin anthelmintics. Parasitology. 2005;131 Suppl:S85-95. doi: 10.1017/S0031182005008218. PMID: 16569295.