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Methoprene
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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 Molecular Structure of 40596-69-8 (METHOPRENE) Hazard Symbols IrritantXi, DangerousN
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

Methoprene Synthetic route

87416-87-3

5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid

A

52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

40596-69-8

methoprene

C

isopropyl 5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylate

Conditions
ConditionsYield
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%
87416-89-5

5-(6-Methoxy-2,6-dimethyl-heptyl)-3-methyl-2,5-dihydro-thiophene-2-carboxylic acid isopropyl ester

A

52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

40596-69-8

methoprene

C

isopropyl 5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylate

Conditions
ConditionsYield
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

(E)-4-Bromo-11-methoxy-3,7,11-trimethyl-dodec-2-enoic acid isopropyl ester

A

52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

40596-69-8

methoprene

C

41797-08-4, 55290-71-6, 58222-78-9, 58223-32-8, 68218-72-4

isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate

Conditions
ConditionsYield
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%
53092-52-7

Methoprene acid

67-63-0

isopropyl alcohol

40596-69-8

methoprene

Conditions
ConditionsYield
(i) SOCl2, (ii) /BRN= 635639/; Multistep reaction;
3613-30-7

7-methoxy-3,7-dimethyloctanal

50798-35-1

diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid

A

52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

40596-69-8

methoprene

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In benzene other reagents; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
917-54-4

methyllithium

80957-93-3

Isopropyl (2Z,4E)-3-Acetoxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate

40596-69-8

methoprene

Conditions
ConditionsYield
With copper(l) iodide 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h; Yield given. Multistep reaction;
917-54-4

methyllithium

80957-87-5, 80957-88-6

Isopropyl (4E)-3-Diethoxyphosphoryloxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate

A

52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

40596-69-8

methoprene

Conditions
ConditionsYield
With copper(l) iodide 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h; Yield given. Multistep reaction. Yields of byproduct given;
103768-96-3

2-(1-Bromo-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester

40596-69-8

methoprene

Conditions
ConditionsYield
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;
616-44-4

3-Methylthiophene

40596-69-8

methoprene

Conditions
ConditionsYield
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
4434-77-9

2-bromo-6-methylhept-5-ene

40596-69-8

methoprene

Conditions
ConditionsYield
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

Methoprene Toxicity Data With Reference

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.

Methoprene Specification

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.

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