(2E,​4E)​-5-​[(2S,​3S)​-​3-​[2-​[(2R)​-​3,​3-​Dimethyloxiranyl]​ethyl]​-​3-​methyloxiranyl]​-​3-​methyl-​2,​4-​pentadienoic Acid Methyl Ester

CAS: 146276-65-5

Ref. TR-D471535

Product Information

• Name: (2E,​4E)​-5-​[(2S,​3S)​-​3-​[2-​[(2R)​-​3,​3-​Dimethyloxiranyl]​ethyl]​-​3-​methyloxiranyl]​-​3-​methyl-​2,​4-​pentadienoic Acid Methyl Ester
• Synonyms: [2S-[2alpha(2E,4E),3beta(S*)]]-5-[3-[2-(3,3-Dimethyloxiranyl)ethyl]-3-methyloxiranyl]-3-methyl-2,4-Pentadienoic Acid Methyl Ester

Description

Applications (2E,​4E)​-5-​[(2S,​3S)​-​3-​[2-​[(2R)​-​3,​3-​Dimethyloxiranyl]​ethyl]​-​3-​methyloxiranyl]​-​3-​methyl-​2,​4-​pentadienoic Acid Methyl Ester is an intermediate in synthesizing Juvenile Hormone B 3 (J211205), a sesquiterpenoid produced by the larval ring gland and adult corpus allatum (CA) of Drosophila melanogaster. Juvenile hormones regulate development, reproduction, diapause, and polyphenisms.
References Wang, Ch., et al.: Gen. Comp. Endocr., 176, 347 (2012); Bendena, W.G., et al.: Gen. Comp. Endocr., 172, 56 (2011); Wyatt, G., Davey, K.: Adv. Insect Physiol., 26, 1 (1996); Nijhout, H.: Insect Hormones (Princeton Univ. Press, Princeton) (1994)

• Brand: TRC

Chemical properties

• Molecular weight: 280.36
• Formula: C₁₆H₂₄O₄
• Color/Form: Yellow
• InChI: InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
• InChI key: InChIKey=CEBXXEKPIIDJHL-UHFFFAOYSA-N
• SMILES: Cc1cc(O)cc2oc(=O)c3c(O)cc(O)cc3c12