(2E,4E)-2,4-Decadien-1-ol - CAS 14507-02-9
Molecular Formula:
C10H18O
Molecular Weight:
154.253
COA:
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Olfactive Family:
Waxy
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Synonyms:
(2E,4E)-deca-2,4-dien-1-ol; (E,E)-2,4-Decadien-1-ol; Trans,trans-2,4-Decadien-1-ol
MSDS:
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InChIKey:
NUBWFSDCZULDCI-BLHCBFLLSA-N
InChI:
InChI=1S/C10H18O/c1-2-3-4-5-6-7-8-9-10-11/h6-9,11H,2-5,10H2,1H3/b7-6+,9-8+
Canonical SMILES:
CCCCCC=CC=CCO
1.Identification of trans,trans-2,4-decadienal metabolites in mouse and human cells using liquid chromatography-mass spectrometry.
Pan KL1, Huang WJ, Hsu MH, Lee HL, Liu HJ, Cheng CW, Tsai MH, Shen MY, Lin P. Chem Res Toxicol. 2014 Oct 20;27(10):1707-19. doi: 10.1021/tx500199b. Epub 2014 Oct 7.
trans,trans-2,4-Decadienal (tt-DDE), a lipid peroxidation product of linolieic acid, is the most abundant aldehyde identified in cooking oil fumes and is readily detectable in food products as well as in restaurant emissions. Previously, we have reported the toxicological effects of tt-DDE in vitro and in vivo. However, the metabolic pathways of tt-DDE in vivo remain unclear. In our present study, we combined liquid chromatography-mass spectrometry with triple quadrupole and time-of-flight to identify tt-DDE metabolites in the urine of mice orally administered tt-DDE. We identified two tt-DDE metabolites, 2,4-decadienoic acid and cysteine-conjugated 2,4-decadien-1-ol, in the urine of mice gavaged with tt-DDE and in human hepatoma cell cultures. The structure of 2,4-decadienoic acid was confirmed upon comparison of its tandem mass spectrometry (MS/MS) spectrum and retention time with those of synthetic standards. The moieties of cysteine and alcohol on cysteine-conjugated 2,4-decadien-1-ol were validated by treating cell cultures with stable-isotope-labeled cysteine and 4-methylpyrazole, an alcohol dehydrogenase inhibitor.
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