More Information
Alternate Name/Synonyms
Milbemycin A3 A4; Mixture of milbemectin A3 & A4
CAS #
A3: 51596-10-2; A4: 51596-11-3
Chemical Name
(1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-5',6',11,13,22-pentamethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one; (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21R,24S)-6'-ethyl-21,24
Chemical Formula
A3: C31H44O7, A4: C32H46O7
Appearance
White to off-white solid
Solubility
Soluble in ethanol, methanol, DMF, or DMSO.
Storage Temp
-20°C, desiccated
THERAPEUTIC AREA
Insecticide
USE
Milbemycin A3 is an antibiotic derived from Streptomyces with acaricidal activity. The milbemycins are part of a family of macrocyclic lactones that are characterized by the spiroketal ring system that are produced by Streptomyces hygroscopicus subsp. aureolacrimosus and are suggested to stimulate chloride-gated ion channels. Milbemycin A4 is an antibiotic derived from Streptomyces with acaricidal activity. The milbemycins are part of a family of macrocyclic lactones that are characterized by the spiroketal ring system that are produced by Streptomyces hydroscopious subsp. aureolacrimosus and are suggested to stimulate chloride-gated ion channels.
Milbemycin A3 and A4 have been used to synthesize milbemycins α9, α10, α11, α12, α14, α15, α20, α21, α22, α23, α26, α7, δ(2,3), δ(4,26)-milbemycins A3, and A4.
INCHI
InChI=1S/C32H46O7.C31H44O7/c1-6-27-21(4)12-13-31(39-27)17-25-16-24(38-31)11-10-20(3)14-19(2)8-7-9-23-18-36-29-28(33)22(5)15-26(30(34)37-25)32(23,29)35;1-18-7-6-8-23-17-35-28-27(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/h7-10,15,19,21,24-29,33,35H,6,11-14,16-18H2,1-5H3;6-9,14,18,20,22,24-28,32,34H,10-13,15-17H2,1-5H3/b8-7+,20-10+,23-9+;7-6+,19-9+,23-8+/t19-,21-,24+,25-,26-,27+,28+,29+,31+,32+;18-,20-,22+,24+,25-,26-,27+,28+,30-,31+/m00/s1
SMILES
O=C3O[C@@H]5C[C@@]1(O[C@H](C)[C@@H](C)CC1)O[C@H](C/C=C(\C)C[C@H](/C=C/C=C2/[C@]4(O)[C@H](OC2)[C@H](O)C(=C/[C@@H]34)\C)C)C5.O=C5O[C@H]2C[C@H](O[C@]1(O[C@H](CC)[C@@H](C)CC1)C2)C/C=C(\C)C[C@H](/C=C/C=C3/[C@@]4(O)[C@H]5/C=C(/C)[C@@H](O)[C@H]4OC3)C
Handling
Use only in area provided with appropriate exhaust ventilation. Keep away from heat and source of ignition. Empty containers pose a fire risk, evaporate residue under fume hood. Ground all equipment containing material. Do not breathe dust.
Certificate of Analysis 1
Certificate of Analysis 2
Certificate of Analysis 3