ChemicalBook CAS DataBase List 51596-10-2

51596-10-2

Name	MILBEMECTIN A3
CAS	51596-10-2
Molecular Formula	C31H44O7
MDL Number	MFCD04972569
Molecular Weight	528.69
MOL File	51596-10-2.mol

Synonyms

milbemycin milbemycinb-2 milbemycin A3 Milbemycin α1 Milbemycin α1 MILBEMECTIN A3 milbemectine a3 Antibiotic B-41A3 Milbemycin EP Imp B Milbemycin oxime A3 Milbemite Impurity 1 Milbemycin EP Impurity B Milbemycin Oxime EP Impurity B B 41A3, MilbeMycin alpha1, MilbeMectin (+)-Chloropseudoephedrine (hydrochloride) Milbemycin Impurity 2(Milbemycin EP Impurity B) (6R,25R)-5-O-Demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B (25R)-25-Methyl-5β-hydroxy-5-demethoxy-28-O,6β-cyclomilbemycin B Milbemycin B, 5-O-demethyl-28-deoxy-6,28-epoxy-25-methyl-, (6R,25R)-

Chemical Properties

Melting point	212-215°; mp 192-194°
alpha	D20 +106° (c = 0.25 in acetone) (Aoki); D20 +106° (acetone) (Hirama)
Boiling point	725.5±60.0 °C(Predicted)
density	1.21±0.1 g/cm3(Predicted)
storage temp.	0-6°C
solubility	DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
form	A solid
pka	12.46±0.70(Predicted)
color	White to light yellow
InChIKey	ZLBGSRMUSVULIE-HIKHPYAJNA-N
EPA Substance Registry System	Milbemycin A3 (51596-10-2)

Safety Data

RIDADR	2588
HazardClass	6.1(b)
PackingGroup	III

Hazard Information

Description

Milbemycin A₃ is a 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 A₃ is used as a nematocide and insecticide. The acaricidal and nematocidal activity of a mixture of milbemycin A₃ and milbemycin A₄ against adult spider mites, spider mite eggs, and C. elegans are reported at IC₅₀ values of 5.3, 41.1, and 9.5 μg/ml.

Uses

Milbemycin A3 is widely used as a pesticides in agriculture. Milbemycin A3 (Milbemycin EP Impurity B) is an antibiotic with acaricidal activity.

Uses

Milbemycins are a complex family of macrocyclic lactones containing a highly characteristic spiroketal group, produced by Streptomyces hydroscopicus subsp. aureolarcrimosus. Milbemycin A3 is a major member of a group of analogues containing a 25-methyl substituent. Milbemycin A3 is a highly selective and potent nematocide and insecticide. Like the closely related avermectins, milbemycins are thought to act on chloride-gated ion channels.

Definition

ChEBI: Milbemycin A3 is a milbemycin.

Synthesis

Milbemectin A3 is obtained by extracting it from the fermentation of the soil microorganism streptomyces (streptomyces hygroscopicus subsp. aureolacrimosus).

References

[1] LING-YU YANG . New nemadectin congeners with acaricidal and nematocidal activity from Streptomyces microflavus neau3 Y-3[J]. Bioorganic & Medicinal Chemistry Letters, 2013, 23 20: Pages 5710-5713. DOI: 10.1016/j.bmcl.2013.08.002

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