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Name |
Spinosad |
EINECS | 620-162-1 |
CAS No. | 131929-60-7 | Density | 1.167 g/cm3 |
PSA | 111.22000 | LogP | 5.48740 |
Solubility | Spinosyn A: 290 mg l-1 (pH 5); Spinosyn D: 29 mg l-1 (pH 5) | Melting Point |
84oC to 99.5oC |
Formula | C41H65NO10 | Boiling Point | 801.515 °C at 760 mmHg |
Molecular Weight | 731.968 | Flash Point | 438.541 °C |
Transport Information | UN 3077 | Appearance | N/A |
Safety | Risk Codes | N/A | |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
(-)-SpinosynA;A 83543A;Lepicidin A;Spinosyn A; |
Article Data | 2 |
(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione
A
spinosyn A
Conditions | Yield |
---|---|
With silver trifluoromethanesulfonate In dichloromethane for 3h; Yield given. Yields of byproduct given; |
methyl 4-formylbutanoate
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 16 steps 1: (-)-(1S,2R)-N,N-dibutylnorephedrine / hexane; toluene / 72 h / 0 °C 2: 84 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature 3: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C 4: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h 5: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature 6: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C 7: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature 8: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h 9: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C 10: Jones reagent / acetone / 1.5 h / 0 °C 11: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C 12: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene 13: 63 percent / methanolic K2CO3 / 48 h / Heating 14: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C 15: 91 percent / 49percent aq. HF / acetonitrile / 24 h 16: AgOTf3 / CH2Cl2 / 3 h View Scheme |
D-forosamine
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) diethyl azodicarboxylate, PPh3 / 1.) THF, -50 deg C, 10 min, 2.) THF, from -50 to 20 deg C, 3 h 2: AgOTf3 / CH2Cl2 / 3 h View Scheme |
(S)-5-Hydroxy-heptanoic acid methyl ester
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1: 84 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature 2: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C 3: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h 4: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature 5: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C 6: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature 7: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h 8: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C 9: Jones reagent / acetone / 1.5 h / 0 °C 10: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C 11: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene 12: 63 percent / methanolic K2CO3 / 48 h / Heating 13: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C 14: 91 percent / 49percent aq. HF / acetonitrile / 24 h 15: AgOTf3 / CH2Cl2 / 3 h View Scheme |
13,14β-Dihydro A83543A aglycon 9α,17α-bis-O-(TBDMS) ether
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 19 steps 1: t-BuOOH, Triton B / methanol; H2O; tetrahydrofuran / 120 h / Ambient temperature 2: diethyl ether / 0 °C 3: 87 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 4: 85 percent / NaIO4 / tetrahydrofuran; H2O / Ambient temperature 5: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h 6: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4 7: 90 percent / pyridine, DMAP 8: MeOH / 168 h / Heating 9: camphorsulfonic acid / CH2Cl2 / 24 h 10: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h 11: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h 12: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C 13: Jones reagent / acetone / 1.5 h / 0 °C 14: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C 15: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene 16: 63 percent / methanolic K2CO3 / 48 h / Heating 17: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C 18: 91 percent / 49percent aq. HF / acetonitrile / 24 h 19: AgOTf3 / CH2Cl2 / 3 h View Scheme |
(S)-5-(tert-butyldimethylsiloxy)heptanal
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h 2: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature 3: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C 4: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature 5: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h 6: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C 7: Jones reagent / acetone / 1.5 h / 0 °C 8: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C 9: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene 10: 63 percent / methanolic K2CO3 / 48 h / Heating 11: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C 12: 91 percent / 49percent aq. HF / acetonitrile / 24 h 13: AgOTf3 / CH2Cl2 / 3 h View Scheme |
(S)-5-(tert-Butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C 2: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h 3: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature 4: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C 5: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature 6: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h 7: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C 8: Jones reagent / acetone / 1.5 h / 0 °C 9: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C 10: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene 11: 63 percent / methanolic K2CO3 / 48 h / Heating 12: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C 13: 91 percent / 49percent aq. HF / acetonitrile / 24 h 14: AgOTf3 / CH2Cl2 / 3 h View Scheme |
Formic acid 2-((3S,3aR,5aS,7R,8aR,8bS)-7-hydroxy-2-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl)-ethyl ester
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: 90 percent / pyridine, DMAP 2: MeOH / 168 h / Heating 3: camphorsulfonic acid / CH2Cl2 / 24 h 4: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h 5: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h 6: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C 7: Jones reagent / acetone / 1.5 h / 0 °C 8: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C 9: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene 10: 63 percent / methanolic K2CO3 / 48 h / Heating 11: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C 12: 91 percent / 49percent aq. HF / acetonitrile / 24 h 13: AgOTf3 / CH2Cl2 / 3 h View Scheme |
(2R,3aS,5aR,5bS,10aS,10bR)-2-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,5a,5b,6,7,9,9a,10,10a,10b-dodecahydro-1H-8-oxa-cyclopenta[a]fluoren-9-ol
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h 2: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4 3: 90 percent / pyridine, DMAP 4: MeOH / 168 h / Heating 5: camphorsulfonic acid / CH2Cl2 / 24 h 6: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h 7: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h 8: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C 9: Jones reagent / acetone / 1.5 h / 0 °C 10: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C 11: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene 12: 63 percent / methanolic K2CO3 / 48 h / Heating 13: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C 14: 91 percent / 49percent aq. HF / acetonitrile / 24 h 15: AgOTf3 / CH2Cl2 / 3 h View Scheme |
spinosyn A
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: camphorsulfonic acid / CH2Cl2 / 24 h 2: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h 3: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h 4: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C 5: Jones reagent / acetone / 1.5 h / 0 °C 6: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C 7: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene 8: 63 percent / methanolic K2CO3 / 48 h / Heating 9: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C 10: 91 percent / 49percent aq. HF / acetonitrile / 24 h 11: AgOTf3 / CH2Cl2 / 3 h View Scheme |
Lepicidin A with CAS NO. of 131929-60-7 is also called for Spinosyn A ; (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-2-((6-Deoxy-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)-13-(((2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9-ethyl-14-methyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-1H-as-indaceno(3,2-d)oxacyclododecin-7,15-dione ; A 83543A ; CCRIS 8937 ; HSDB 7006 ; LY-232105 ; PP-105 ; Spinosad factor A ; UNII-OY0L59V61N ; 1H-as-Indaceno(3,2-d)oxacyclododecin-7,15-dione, 2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-2-((6-deoxy-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)- 13-((5-dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9-ethyl-14-methyl-, (2R-(2R*,3aS*,5aR*,5bS*,9S*,13S*(2R*,5S*,6R*),14R*,16aS*,16bR*))- ; 1H-as-Indaceno(3,2-d)oxacyclododecin-7,15-dione, 2-((6-deoxy-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)-13-(((2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-14-methyl-,(2R,3aS,5aR,5bS,9S,13S, 14R ,16aS, 16bR) - and so on.
Molecular Formula: C41H65NO10
Molecular Weight: 731.96
ACD/LogP: 4.80
ACD/LogD (pH 5.5): 1.99
ACD/LogD (pH 7.4): 3.56
ACD/BCF (pH 5.5): 4.06
ACD/BCF (pH 7.4): 151.13
ACD/KOC (pH 5.5): 15.11
ACD/KOC (pH 7.4): 562.62
H bond acceptors: 11
H bond donors: 0
Freely Rotating Bonds: 9
Heavy Atom Count: 52
Formal Charge: 0
Complexity: 1290
Isotope Atom Count: 0
Defined Atom StereoCenter Count: 16
Undefined Atom StereoCenter Count: 1
Defined Bond StereoCenter Count: 0
Undefined Bond StereoCenter Count: 0
Covalently-Bonded Unit Count: 1
Index of Refraction: 1.54
Molar Refractivity: 196.9 cm3
Molar Volume: 627.2 cm3
Surface Tension: 45.8 dyne/cm
Density: 1.16 g/cm3
Flash Point: 438.5°C
Enthalpy of Vaporization: 116.54 kJ/mol
Boiling Point: 801.5°C at 760 mmHg
Vapour Pressure: 1.04E-25 mmHg at 25°C
The molecular structure of Lepicidin A with CAS NO. of 131929-60-7:
Lepicidin A with CAS NO. of 131929-60-7 is used as pediculicide.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD | oral | > 400mg/kg (400mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | National Technical Information Service. Vol. OTS0543604, |
mouse | LDLo | oral | 500mg/kg (500mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | National Technical Information Service. Vol. OTS0543562, |
rat | LC50 | inhalation | > 499mg/m3/4H (499mg/m3) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER | National Technical Information Service. Vol. OTS0534564, |
rat | LD | oral | > 2gm/kg (2000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER | National Technical Information Service. Vol. OTS0543570, |
Moderately toxic by ingestion and inhalation. When heated to decomposition it emits toxic vapors of NOx.
RIDADR: 3077
HazardClass: 9
PackingGroup: III
Hazardous Substances Data: 131929-60-7(Hazardous Substances Data)