(E)-2-Decenoic acid - CAS 334-49-6
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Not Intended for Therapeutic Use. For research use only.
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trans-2-Decenoic Acid is isolated along with 10-hydroxy-trans-2-decenoic acid, a fatty acid unique to royal jelly.(E)-2-decanoic acid(trans-2-Decenoic Acid) and 10-hydroxy-trans-2-decenoic acid are both described to demonstrate estrogenic activity, where the fatty acids demonstrate inhibition of 17β-estradiol binding to estrogen receptor-β.
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trans-2-Decenoic acid
1.Engineering Escherichia coli for the synthesis of short- and medium-chain α,β-unsaturated carboxylic acids.
Kim S1, Cheong S1, Gonzalez R2. Metab Eng. 2016 Mar 17;36:90-98. doi: 10.1016/j.ymben.2016.03.005. [Epub ahead of print]
Concerns over sustained availability of fossil resources along with environmental impact of their use have stimulated the development of alternative methods for fuel and chemical production from renewable resources. In this work, we present a new approach to produce α,β-unsaturated carboxylic acids (α,β-UCAs) using an engineered reversal of the β-oxidation (r-BOX) cycle. To increase the availability of both acyl-CoAs and enoyl-CoAs for α,β-UCA production, we use an engineered Escherichia coli strain devoid of mixed-acid fermentation pathways and known thioesterases. Core genes for r-BOX such as thiolase, hydroxyacyl-CoA dehydrogenase, enoyl-CoA hydratase, and enoyl-CoA reductase were chromosomally overexpressed under the control of a cumate inducible phage promoter. Native E. coli thioesterase YdiI was used as the cycle-terminating enzyme, as it was found to have not only the ability to convert trans-enoyl-CoAs to the corresponding α,β-UCAs, but also a very low catalytic efficiency on acetyl-CoA, the primer and extender unit for the r-BOX pathway.
2.Gas chromatographic-mass spectrometric investigation of volatile and extractable compounds of crude royal jelly.
Isidorov VA1, Bakier S, Grzech I. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Feb 15;885-886:109-16. doi: 10.1016/j.jchromb.2011.12.025. Epub 2011 Dec 30.
Using headspace solid-phase microextraction (HS-SPME) followed by diethyl ether and methanol extraction, it was possible to isolate as many as 185 organic compounds out of 17 samples of crude royal jelly (RJ). Of the above compound number, 169 compounds were positively identified by means of gas chromatography-mass spectrometry. The volatile fraction of RJ consists of 25 different compounds where approximately 47% of the total ion current (TIC) of volatile compound chromatograms were composed of substances characterized by bactericidal (phenols) and repelling (octanoic acid and 2-heptanone) activities. Preliminary investigations have shown that RJ stored for 10 months at -18°C and 4°C keeps its composition of volatile compounds unchanged, however, at the same time at room temperature RJ phenol contents is decreased twice, whereas the fraction of aliphatic acids is increased 2.8 times due to the presence of both acetic and butyric acids. The chromatogram of RJ ether extracts showed 85 different compounds, however about 88% of TIC consisted exclusively of 8 compounds, i.
3.2-decenoic acid ethyl ester, a compound that elicits neurotrophin-like intracellular signals, facilitating functional recovery from cerebral infarction in mice.
Tanaka Y1, Fukumitsu H, Soumiya H, Yoshimura S, Iwama T, Furukawa S. Int J Mol Sci. 2012;13(4):4968-81. doi: 10.3390/ijms13044968. Epub 2012 Apr 19.
In our previous study, we found that trans-2-decenoic acid ethyl ester (DAEE), a derivative of a medium-chain fatty acid, elicits neurotrophin-like signals including the activation of extracellular signal-regulated kinases 1 and 2 (ERK1/2) in cultured mouse cortical neurons. Here, we examined the efficacy of intraperitoneal administration of DAEE on the treatment of a mouse model of the cerebral infarction caused by unilateral permanent middle cerebral artery occlusion (PMCAO). DAEE-treatment (100 μg/kg body weight injected at 0.5, 24, 48, 72 h after PMCAO) significantly restored the mice from PMCAO-induced neurological deficits including motor paralysis when evaluated 48, 72, and 96 h after the PMCAO. Furthermore, DAEE facilitated the phosphorylation of ERK1/2 on the infarction side of the brain when analyzed by Western immunoblot analysis, and it enhanced the number of phosphorylated ERK1/2-positive cells in the border areas between the infarction and non-infarction regions of the cerebral cortex, as estimated immunohistochemically.
4.Unsaturated fatty acid, cis-2-decenoic acid, in combination with disinfectants or antibiotics removes pre-established biofilms formed by food-related bacteria.
Sepehr S1, Rahmani-Badi A1, Babaie-Naiej H1, Soudi MR1. PLoS One. 2014 Jul 7;9(7):e101677. doi: 10.1371/journal.pone.0101677. eCollection 2014.
Biofilm formation by food-related bacteria and food-related pathogenesis are significant problems in the food industry. Even though much disinfection and mechanical procedure exist for removal of biofilms, they may fail to eliminate pre-established biofilms. cis-2 decenoic acid (CDA), an unsaturated fatty acid messenger produced by Pseudomonas aeruginosa, is reportedly capable of inducing the dispersion of established biofilms by multiple types of microorganisms. However, whether CDA has potential to boost the actions of certain antimicrobials is unknown. Here, the activity of CDA as an inducer of pre-established biofilms dispersal, formed by four main food pathogens; Staphylococcus aureus, Bacillus cereus, Salmonella enterica and E. coli, was measured using both semi-batch and continuous cultures bioassays. To assess the ability of CDA combined biocides treatments to remove pre-established biofilms formed on stainless steel discs, CFU counts were performed for both treated and untreated cultures.
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CAS 334-49-6 (E)-2-Decenoic acid

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