10-Undecylenic Acid - CAS 112-38-9
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
10-Undecylenic Acid
Catalog Number:
112-38-9
Synonyms:
undec-10-enoicacid;10-UNDECENOICACID;undecylenicacid;Undec-10-enoicacid;Undecenoicacid;112-38-9
CAS Number:
112-38-9
Description:
10-Undecylenic Acid, a long-chain fatty acid substance, could be used as a monomer in the polymerization and also a raw material in the syntheses of Pheromone (11Z)-hexadecenal.
Molecular Weight:
184.28
Molecular Formula:
C11H20O2
Quantity:
Grams-Kilos
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C=CCCCCCCCCC(=O)O
InChI:
InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)
InChIKey:
FRPZMMHWLSIFAZ-UHFFFAOYSA-N
Targets:
Others
Chemical Structure
CAS 112-38-9 10-Undecylenic Acid

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Reference Reading


1.An Involvement of PI3-K/Akt Activation and Inhibition of AIF Translocation in Neuroprotective Effects of Undecylenic Acid (UDA) Against Pro-Apoptotic Factors-Induced Cell Death in Human Neuroblastoma SH-SY5Y Cells.
Jantas D1, Piotrowski M2, Lason W1. J Cell Biochem. 2015 Dec;116(12):2882-95. doi: 10.1002/jcb.25236.
Undecylenic acid (UDA), a naturally occurring 11-carbon unsaturated fatty acid, has been used for several years as an economical antifungal agent and a nutritional supplement. Recently, the potential usefulness of UDA as a neuroprotective drug has been suggested based on the ability of this agent to inhibit μ-calpain activity. In order to verify neuroprotective potential of UDA, we tested protective efficacy of this compound against cell damage evoked by pro-apoptotic factors (staurosporine and doxorubicin) and oxidative stress (hydrogen peroxide) in human neuroblastoma SH-SY5Y cells. We showed that UDA partially protected SH-SY5Y cells against the staurosporine- and doxorubicin-evoked cell death; however, this effect was not connected with its influence on caspase-3 activity. UDA decreased the St-induced changes in mitochondrial and cytosolic AIF level, whereas in Dox-model it affected only the cytosolic AIF content. Moreover, UDA (1-40 μM) decreased the hydrogen peroxide-induced cell damage which was connected with attenuation of hydrogen peroxide-mediated necrotic (PI staining, ADP/ATP ratio) and apoptotic (mitochondrial membrane potential, caspase-3 activation, AIF translocation) changes.
2.Microwave-assisted pyrolysis of methyl ricinoleate for continuous production of undecylenic acid methyl ester (UAME).
Nie Y1, Duan Y1, Gong R1, Yu S1, Lu M1, Yu F1, Ji J1. Bioresour Technol. 2015 Jun;186:334-7. doi: 10.1016/j.biortech.2015.03.076. Epub 2015 Mar 19.
Undecylenic acid methyl ester (UAME) was continuously produced from methyl ricinoleate using a microwave-assisted pyrolysis system with atomization feeding. The UAME yield of 77 wt.% was obtained at 500°C using SiC as the microwave absorbent and heating medium. The methyl ricinoleate conversion and UAME yield from microwave-assisted pyrolysis process were higher than those from conventional pyrolysis. The effect of temperature on the pyrolysis process was also investigated. The methyl ricinoleate conversion increased but the cracking liquid yield decreased when the temperature increased from 460°C to 560°C. The maximum UAME yield was obtained at the temperature of 500°C.
3.Antifungal effects of undecylenic acid on the biofilm formation of Candida albicans.
Shi D, Zhao Y, Yan H, Fu H, Shen Y, Lu G, Mei H, Qiu Y, Li D, Liu W. Int J Clin Pharmacol Ther. 2016 May;54(5):343-53. doi: 10.5414/CP202460.
Undecylenic acid can effectively control skin fungal infection, but the mechanism of its fungal inhibition is unclear. Hyphal growth of Candida albicans (C. albicans) and biofilm formation have been well recognized as important virulence factors for the initiation of skin infection and late development of disseminated infection. In this study, we seek to investigate antifungal mechanisms of undecylenic acid by evaluating the virulence factors of C. albicans during biofilm formation. We found that undecylenic acid inhibits biofilm formation of C. albicans effectively with optimal concentration above 3 mM. In the presence of this compound, the morphological transition from yeast to filamentous phase is abolished ultimately when the concentration of undecylenic acid is above 4 mM. Meanwhile, the cell surface is crumpled, and cells display an atrophic appearance under scanning electron microscopy even with low concentration of drug treatment.
4.Polyelectrolyte-coated nanocapsules containing undecylenic acid: Synthesis, biocompatibility and neuroprotective properties.
Piotrowski M1, Jantas D2, Szczepanowicz K1, Łukasiewicz S3, Lasoń W2, Warszyński P4. Colloids Surf B Biointerfaces. 2015 Nov 1;135:8-17. doi: 10.1016/j.colsurfb.2015.07.029. Epub 2015 Jul 19.
The main objectives of the present study were to investigate the biocompatibility of polyelectrolyte-coated nanocapsules and to evaluate the neuroprotective action of the nanoencapsulated water-insoluble neuroprotective drug-undecylenic acid (UDA), in vitro. Core-shell nanocapsules were synthesized using nanoemulsification and the layer-by-layer (LbL) technique (by saturation method). The average size of synthesized nanocapsules was around 80 nm and the concentration was 2.5 × 10(10) particles/ml. Their zeta potential values ranged from less than -30 mV for the ones with external polyanion layers through -4 mV for the PEG-ylated layers to more than 30 mV for the polycation layers. Biocompatibility of synthesized nanocarriers was evaluated in the SH-SY5Y human neuroblastoma cell line using cell viability/toxicity assays (MTT reduction, LDH release). The results obtained showed that synthesized nanocapsules coated with PLL and PGA (also PEG-ylated) were non-toxic to SH-SY5Y cells, therefore, they were used as nanocarriers for UDA.