methyl (2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienoate

• ChemBase ID: 132518
• Molecular Formular: C16H26O3
• Molecular Mass: 266.37584
• Monoisotopic Mass: 266.18819469
• SMILES: C/C(=C\CC/C(=C/C(=O)OC)/C)/CCC1C(O1)(C)C
• Canonical SMILES: COC(=O)/C=C(/CC/C=C(/CCC1OC1(C)C)\C)\C
• InChI: InChI=1S/C16H26O3/c1-12(9-10-14-16(3,4)19-14)7-6-8-13(2)11-15(17)18-5/h7,11,14H,6,8-10H2,1-5H3/b12-7+,13-11+
• InChIKey: QVJMXSGZTCGLHZ-ZPLWXOMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienoate; methyl 9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienoate
• IUPAC Traditional name: methyl (2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienoate; methyl 9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienoate
• Synonyms: (2E,6E)- 9-(3,3-Dimethyl-2-oxiranyl)-3,7-dimethyl-2,6-nonadienoic Acid Methyl Ester; (E,E)-(±)-10,11-Epoxy-3,7,11-trimethyl-2,6-dodecadienoic Acid Methyl Ester; (E,E)-Methyl 3,7,11-trimethyl-10,11-epoxy-2,6-dodecadienoate; (±)-Juvenile Hormone III; Methyl RS-(±)-10,11-Epoxyfarnesate; trans-trans-10,11-Epoxy Farnesenic Acid Methyl Ester; C16-Juvenile Hormone; JH-III; Manduca hormone; trans,trans-10,11-Epoxy-3,7,11-trimethyl-2,6-dodecadienic acid methyl ester; Juvenile hormone III

Database IDs

• CAS Number: 24198-95-6
• EC Number: 246-072-9
• MDL Number: MFCD00135990
• Beilstein Number: 1316317
• PubChem SID: 162226795; 24881770; 24896191
• PubChem CID: 5367549

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.8828642
• LogD (pH = 7.4): 3.8828642
• Log P: 3.8828642
• Molar Refractivity: 78.4587 cm^3
• Polarizability: 30.442617 Å^3
• Polar Surface Area: 38.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~80% (HPLC); ≥65%
• Empirical Formula (Hill Notation): C16H26O3

DETAILS

Sigma Aldrich - J2000

Biochem/physiol Actions
Controls the larval metamorphosis of insects, including the retention of juvenile characteristics.

Sigma Aldrich - 59992

Biochem/physiol Actions
Controls the larval metamorphosis of insects, including the retention of juvenile characteristics.

Toronto Research Chemicals - E589400

trans-trans-10,11-Epoxy Farnesenic Acid Methyl Ester is a metabolite (2E,6E)-Farnesenic Acid.

REFERENCES

• Koeppe, J., et al.: J. Biol. Chem., 259, 3219 (1984)
• King, L., et al.: Insect. Biochem., 18, 793 (1984)
• Park, Y., et al.: Biochemistry, 32, 7909 (1984)