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Cis-11-Eicosenoic acid

CAS# 5561-99-9

Cis-11-Eicosenoic acid

Catalog No. BCX1369----Order now to get a substantial discount!

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Chemical structure

Cis-11-Eicosenoic acid

Chemical Properties of Cis-11-Eicosenoic acid

Cas No. 5561-99-9 SDF Download SDF
PubChem ID N/A Appearance Powder
Formula C20H38O2 M.Wt 310.52
Type of Compound Aliphatics Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Cis-11-Eicosenoic acid Dilution Calculator

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Cis-11-Eicosenoic acid Molarity Calculator

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Preparing Stock Solutions of Cis-11-Eicosenoic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2204 mL 16.102 mL 32.204 mL 64.4081 mL 80.5101 mL
5 mM 0.6441 mL 3.2204 mL 6.4408 mL 12.8816 mL 16.102 mL
10 mM 0.322 mL 1.6102 mL 3.2204 mL 6.4408 mL 8.051 mL
50 mM 0.0644 mL 0.322 mL 0.6441 mL 1.2882 mL 1.6102 mL
100 mM 0.0322 mL 0.161 mL 0.322 mL 0.6441 mL 0.8051 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Cis-11-Eicosenoic acid

Dietary Chinese herbal formula supplementation improves yolk fatty acid profile in aged laying hens.[Pubmed:38404134]

Vet Q. 2024 Dec;44(1):1-11.

Chinese herbal formula (CHF) has the potential to improve the performance of aged laying hens through integrated regulation of various physiological functions. The present study aimed to investigate the effects of dietary CHF supplementation on the yolk fatty acid profile in aged laying hens. A total of 144 healthy 307-day-old Xinyang black-feather laying hens were randomly allocated into two groups: a control group (CON, fed a basal diet) and a CHF group (fed a basal diet supplemented with 1% CHF; contained 0.30% Leonurus japonicus Houtt., 0.20% Salvia miltiorrhiza Bge., 0.25% Ligustrum lucidum Ait., and 0.25% Taraxacum mongolicum Hand.-Mazz. for 120 days). The fatty acid concentrations in egg yolks were analyzed using a targeted metabolomics technology at days 60 and 120 of the trial. The results showed that dietary CHF supplementation increased (p < .05) the concentrations of several saturated fatty acids (SFA, including myristic acid and stearic acid), monounsaturated fatty acids (MUFA, including petroselinic acid, elaidic acid, trans-11-eicosenoic acid, and Cis-11-Eicosenoic acid), polyunsaturated fatty acids (PUFA, including linolelaidic acid, linoleic acid, gamma-linolenic acid, alpha-linolenic acid, 11c,14c-eicosadienoic acid, eicosatrienoic acid, homo-gamma-linolenic acid, arachidonic acid, and docosapentaenoic acid), and fatty acid indexes (total MUFA, n-3 and n-6 PUFA, PUFA/SFA, hypocholesterolemic/hypercholesterolaemic ratio, health promotion index, and desirable fatty acids) in egg yolks. Collectively, these findings suggest that dietary CHF supplementation could improve the nutritional value of fatty acids in egg yolks of aged laying hens, which would be beneficial for the production of healthier eggs to meet consumer demands.

NEFA can serve as good biological markers for the diagnosis of depression in adolescents.[Pubmed:38364978]

J Affect Disord. 2024 May 1;352:342-348.

BACKGROUND: The incidence of adolescent depression has markedly risen in recent years, with a high recurrence rate into adulthood. Diagnosis in adolescents is challenging due to subjective factors, highlighting the crucial need for objective diagnostic markers. METHODS: Our study enrolled 204 participants, including healthy controls (n = 88) and first-episode adolescent depression patients (n = 116). Serum samples underwent gas chromatography-mass spectrometry (GC-MS) analysis to assess non-esterified fatty acids (NEFA) expression. Machine learning and ROC analysis were employed to identify potential biomarkers, followed by bioinformatics analysis to explore underlying mechanisms. RESULTS: Nearly all differentially expressed NEFA exhibited significant downregulation. Notably, nonanoic acid, cis-10-pentadecenoic acid, cis-10-carboenoic acid, and Cis-11-Eicosenoic acid demonstrated excellent performance in distinguishing adolescent depression patients. Metabolite-gene interaction analysis revealed these NEFAs interacted with multiple genes. KEGG pathway analysis on these genes suggested that differentially expressed NEFA may impact PPAR and cAMP signaling pathways. LIMITATIONS: Inclusion of diverse populations for evaluation is warranted. Biomarkers identified in this study require samples that are more in line with the experimental design for external validation, and further basic research is necessary to validate the potential depressive mechanisms of NEFA. CONCLUSIONS: The overall reduction in NEFA expression in first-episode adolescent depression patients suggests a potential mediation of depression symptoms through cAMP and PPAR signaling pathways. NEFA levels show promise as a diagnostic tool for identifying first-episode adolescent depression patients.

Metabolome and transcriptome profiling in different bagging pear fruit reveals that PbKCS10 affects the occurrence of superficial scald via regulating the wax formation.[Pubmed:37130451]

Food Chem. 2023 Oct 1;422:136206.

Superficial scald is a physiological disorder of fruit, which is easy to occur during long-term cold storage after harvest. Different preharvest bagging treatments (no bagging, polyethylene bagging and non-woven fabric bagging) were used to explore the occurrence mechanism of superficial scald. UHPLC-MS analysis, GC-MS analysis and RNA-seq revealed the influence of the wax of 'Chili' on the occurrence of superficial scald. The wax content and wax components (Lupeol, lup-20(29)-en-3-one, heptacosane, 9-octadecenoic acid, eicosanoic acid, Cis-11-Eicosenoic acid) were significantly higher in the fruit bagged with non-woven fabric (NWF, with low incidence of superficial scald) than that in fruit bagged with polyethylene (PE, high incidence of superficial scald). Transcriptomics and qRT-PCR data identified a wax synthesis gene, PbKCS10, which exhibited high expression levels in fruit with low of superficial scald. The results of gene function showed that PbKCS10 reduced the occurrence of superficial scald by increasing the wax formation.

Bovine milk-derived extracellular vesicles prevent gut inflammation by regulating lipid and amino acid metabolism.[Pubmed:36757176]

Food Funct. 2023 Feb 21;14(4):2212-2222.

Inflammatory bowel disease (IBD) is a global health problem in which metabolite alteration plays an important pathogenic role. Bovine milk-derived extracellular vesicles (mEVs) have been shown to regulate nutrient metabolism in healthy animal models. This study investigated the effect of oral mEVs on metabolite changes in DSS-induced murine colitis. We performed metabolomic profiling on plasma samples and measured the concentrations of lipids and amino acids in both fecal samples and colonic tissues. Plasma metabolome analysis found that mEVs significantly upregulated 148 metabolite levels and downregulated 44 metabolite concentrations (VIP > 1, and p < 0.05). In the fecal samples, mEVs significantly increased the contents of acetate and butyrate and decreased the levels of tridecanoic acid (C13:0), methyl cis-10-pentadecenoate (C15:1) and Cis-11-Eicosenoic acid (C20:1). Moreover, the concentrations of eicosadienoic acid (C20:2), eicosapentaenoic acid (C20:5), and docosahexaenoic acid (C22:6) were decreased in colonic tissues with mEV supplementation. In addition, compared with the DSS group, mEVs significantly increased the content of L-arginine, decreased the level of L-valine in the fecal samples, and also decreased the levels of L-serine and L-glutamate in the colonic tissues. Collectively, our findings demonstrated that mEVs could recover the metabolic abnormalities caused by inflammation and provided novel insights into mEVs as a potential modulator for metabolites to prevent and treat IBD.

Possible Mechanism of Dysphania ambrosioides (L.) Mosyakin & Clemants Seed Extract Suppresses the Migration and Invasion of Human Hepatocellular Carcinoma Cells SMMC-7721.[Pubmed:36694378]

Chem Biodivers. 2023 Mar;20(3):e202200768.

Mexican tea (Dysphania ambrosioides (L.) Mosyakin & Clemants) is rich in phenolic acids and flavonoids and could be a potential medicinal herb that can be used for prevention of human hepatocellular carcinoma. The objective of this study was to elaborate the possible mechanism for the prevention or treatment of hepatocellular carcinoma using Mexican tea, and to provide new avenues for the utilization of the invasive plant. In this study, the D. ambrosioides seed extracts (CSE) were analyzed by gas chromatography-mass spectrometry, and the effects of CSE on proliferation, migration, invasion, and gene expression of SMMC-7721 cells were investigated. Eight compounds were identified in CSE, and the compound with the highest content was ascaridole (25.82 %). The proliferation was significantly inhibited by CSE (p<0.05), and IC(50) values were 0.587 g/L, 0.360 g/L, and 0.361 g/L at 24 h, 36 h, and 48 h, respectively. Migration and invasion were significantly inhibited (p<0.05). The network pharmacology and transcriptome analysis indicated that 2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one, Cis-11-Eicosenoic acid and 2-ethylcyclohexanone might be the active compounds. Transcriptome analysis indicated that the Wnt signaling pathway, which is related to migration and invasion, was significantly altered; this was verified by western blot assay. The expression of wnt11, lef1 and mmp7 genes in SMMC-7721 cells was significantly down-regulated (p<0.05), while gsk-3beta was significantly up-regulated (p<0.05). These results indicate that CSE inhibits the invasion and migration of SMMC-7721 cells in hepatocellular carcinoma through the Wnt signaling pathway.

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