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Name |
Methoprene |
EINECS | 254-993-2 |
CAS No. | 40596-69-8 | Density | 0.914 g/cm3 |
PSA | 35.53000 | LogP | 5.06200 |
Solubility | Miscible | Melting Point |
164oC |
Formula | C19H34O3 | Boiling Point | 385.7 °C at 760 mmHg |
Molecular Weight | 310.477 | Flash Point | 162.4 °C |
Transport Information | UN 3082 9/PG 3 | Appearance | N/A |
Safety | 26-36-60-61 | Risk Codes | 36/37/38-51/53 |
Molecular Structure | Hazard Symbols | Xi, N | |
Synonyms |
2,4-Dodecadienoicacid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl ester, (E,E)-;(2E,4E)-3,7,11-Trimethyl-11-methoxydodeca-2,4-dienoic acid ethyl ester;Altosid;Altosid Liquid Larvicide;Altosid SR 10;Altosid XR;Apex 600E;Isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate;Juvemon;Juvenmon;Manina;Manta;Manta (hormone);Starbar Inhibitor;ZPA 1019; |
Article Data | 15 |
5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 20% |
5-(6-Methoxy-2,6-dimethyl-heptyl)-3-methyl-2,5-dihydro-thiophene-2-carboxylic acid isopropyl ester
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 20% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Product distribution; | A n/a B n/a C 90 mg |
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
C
isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate
Conditions | Yield |
---|---|
With lithium carbonate; lithium bromide In N,N-dimethyl-formamide for 1h; Heating; Yield given. Title compound not separated from byproducts; | A n/a B 0.18 g C 10% |
With lithium carbonate; lithium bromide In N,N-dimethyl-formamide for 1h; Heating; Yields of byproduct given; | A n/a B 0.18 g C 10% |
Conditions | Yield |
---|---|
(i) SOCl2, (ii) /BRN= 635639/; Multistep reaction; |
7-methoxy-3,7-dimethyloctanal
diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In benzene other reagents; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
methyllithium
Isopropyl (2Z,4E)-3-Acetoxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate
methoprene
Conditions | Yield |
---|---|
With copper(l) iodide 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h; Yield given. Multistep reaction; |
methyllithium
Isopropyl (4E)-3-Diethoxyphosphoryloxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate
A
Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
B
methoprene
Conditions | Yield |
---|---|
With copper(l) iodide 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h; Yield given. Multistep reaction. Yields of byproduct given; |
2-(1-Bromo-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester
methoprene
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc dibromide 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h; Multistep reaction; |
3-Methylthiophene
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 2: 77 percent / H2SO4 conc. / 4 h / Heating 3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 5: diethyl ether / 0.5 h / 0 °C 6: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 2: 77 percent / H2SO4 conc. / 4 h / Heating 3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 5: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
2-bromo-6-methylhept-5-ene
methoprene
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min 2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 3: pyridine; diethyl ether / 6 h / Heating 4: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 5: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 6: 77 percent / H2SO4 conc. / 4 h / Heating 7: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 8: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 9: diethyl ether / 0.5 h / 0 °C 10: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min 2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 3: pyridine; diethyl ether / 6 h / Heating 4: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 5: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 6: 77 percent / H2SO4 conc. / 4 h / Heating 7: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 8: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 9: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme |
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | 5gm/kg (5000mg/kg) | EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976. | |
guinea pig | LC50 | inhalation | > 210gm/m3 (210000mg/m3) | EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976. | |
rabbit | LD50 | oral | 3038mg/kg (3038mg/kg) | "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A615, Pg. 1986, | |
rabbit | LD50 | skin | 3gm/kg (3000mg/kg) | EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976. | |
rat | LC50 | inhalation | > 210gm/m3 (210000mg/m3) | EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976. | |
rat | LD50 | oral | 25gm/kg (25000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 56(10), Pg. 72, 1991. |
The Methoprene, with the CAS registry number 40596-69-8, is also known as Isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4 dodecadienoate. It belongs to the product categories of Growth regulatorsPesticides&Metabolites;H-MAlphabetic.This chemical's molecular formula is C19H34O3 and molecular weight is 310.47. What's more,Its systematic name is Isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4 dodecadienoate.It is a juvenile hormone analog and insect growth regulator used to control insects by disrupting metamorphosis. Has been effective in controlling mosquito larvae.
Physical properties about Methoprene are:
(1)ACD/LogP: 5.625; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.63; (4)ACD/LogD (pH 7.4): 5.63; (5)ACD/BCF (pH 5.5): 11084.06; (6)ACD/BCF (pH 7.4): 11084.06; (7)ACD/KOC (pH 5.5): 27339.10; (8)ACD/KOC (pH 7.4): 27339.10; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 11; (12)Index of Refraction: 1.462; (13)Molar Refractivity: 93.435 cm3; (14)Molar Volume: 339.84 cm3; (15)Surface Tension: 29.636999130249 dyne/cm; (16)Density: 0.914 g/cm3; (17)Flash Point: 162.376 °C; (18)Enthalpy of Vaporization: 63.453 kJ/mol; (19)Boiling Point: 385.697 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:O=C(OC(C)C)\C=C(\C=C\CC(CCCC(OC)(C)C)C)C;
(2)Std. InChI:InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+;
(3)Std. InChIKey:NFGXHKASABOEEW-LDRANXPESA-N.
Safety Information of Methoprene chloride:
The Methoprene is irritating to eyes, respiratory system and skin.It is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.Avoid release to the environment. Refer to special instructions safety data sheet. When you use it ,wear suitable protective clothing.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.This material and/or its container must be disposed of as hazardous waste.
The toxicity data of Methoprene as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | 5gm/kg (5000mg/kg) | EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976. | |
guinea pig | LC50 | inhalation | > 210gm/m3 (210000mg/m3) | EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976. | |
rabbit | LD50 | oral | 3038mg/kg (3038mg/kg) | "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A615, Pg. 1986, | |
rabbit | LD50 | skin | 3gm/kg (3000mg/kg) | EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976. | |
rat | LC50 | inhalation | > 210gm/m3 (210000mg/m3) | EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976. | |
rat | LD50 | oral | 25gm/kg (25000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 56(10), Pg. 72, 1991. |