Ethyl (2E,4Z)-deca-2,4-dienoate → 2,4-Decadienoic acid, methyl ester, (2E,4Z)-

HRID 2399217Notes

Reaction equation

HRID 2399217 reaction equation
[C:1]([O:12][CH2:13]C)(=[O:11])/[CH:2]=[CH:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>CO>[C:1]([O:12][CH3:13])(=[O:11])/[CH:2]=[CH:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

3

Reactant 1

HCID 5281162Ethyl (2E,4Z)-deca-2,4-dienoate

Product 1

HCID 64363362,4-Decadienoic acid, methyl ester, (2E,4Z)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mass spectra (MS) were obtained in the electron impact mode at 70 eV using a Finnigan 4510 GC-MS. The MS of the major male-specific compound detected in E. conspersus aeration samples gave a prominent molecular ion a m/z 182 (ca. 20%), but a matching spectrum was not found in the GC-MS computer library of spectra (>31,000 MS) (FIG. 2). The presence of an M-31 peak at m/z 151 suggested a methyl ester structure for this component, as did ions at m/z 59 ([O=C--O--CH3 ]+) and m/z 74 ([CH2 =C(OH)--OCH3 ]+). Thus, the molecular formula was deduced to be C11H18O2 and a di-unsaturated, unbranched acidic moiety was thought most likely. A 20 g sample of the related compound, ethyl (2E,4Z)-decadienoate (called the pear ester), was obtained from International Flavors & Fragrances Inc. (IFF, Union Beach, N.J.). The pear ester standard was saponified and re-esterified with methanol by normal procedures to give methyl (2E,4Z)-decadienoate and a small percentage of the corresponding (2Z,4E)- and (2E,4E)-isomers. This standard of methyl (2E,4Z)-decadienoate gave an identical MS to that of the E. conspersus male-specific compound and the standard coeluted with the unknown by GC.

Workup

  1. customMass spectra (MS) were obtained in the electron impact mode at 70 eV

Sources & evidence

ORD record
ord-fc124f4ddf0f4e9f9a75cb05a892f77e
Source dataset
uspto-grants-1995_09
Patent number
US05447718

Reaction notes

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