112-79-8 | Elaidic acid

Packsize	Purity	Availability	Price	Discounted Price
50mg	96%	in stock	$20.00	$14.00
100mg	96%	in stock	$33.00	$23.00
250mg	96%	in stock	$46.00	$32.00
1g	96%	in stock	$50.00	$35.00
5g	96%	in stock	$163.00	$114.00
25g	96%	in stock	$472.00	$330.00

Description

• Catalog Number: AD37901
• Chemical Name: Elaidic acid
• CAS Number: 112-79-8
• Molecular Formula: C18H34O2
• Molecular Weight: 282.4614
• MDL Number: MFCD00063954
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)O
• NSC Number: 26988

Computed Properties

• Complexity: 234
• Covalently-Bonded Unit Count: 1
• Defined Bond Stereocenter Count: 1
• Heavy Atom Count: 20
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 15
• XLogP3: 6.5

Upstream Synthesis Route

(E)-Octadec-9-enoic acid, also known as oleic acid, is a valuable compound used extensively in chemical synthesis. It serves as a crucial building block in the production of various chemicals and materials due to its versatile nature and reactivity. One primary application of (E)-Octadec-9-enoic acid is in the preparation of ester derivatives, which are widely used in the production of soaps, detergents, cosmetics, and pharmaceuticals. Additionally, (E)-Octadec-9-enoic acid is utilized in the synthesis of bioactive compounds, such as surfactants, emollients, and lubricants, due to its ability to impart desirable properties to the final products. Its versatile functionality and compatibility with a wide range of chemical reactions make (E)-Octadec-9-enoic acid an indispensable component in the realm of chemical synthesis.

Literature

• Self-assembled nanostructures of fully hydrated monoelaidin-elaidic acid and monoelaidin-oleic acid systems.

  Langmuir : the ACS journal of surfaces and colloids 20120703

• Trans fatty acids: induction of a pro-inflammatory phenotype in endothelial cells.

  Lipids 20120701

• Identification of a potential biomarker panel for the intake of the common dietary trans fat elaidic acid (trans∆9-C18:1).

  Journal of proteomics 20120517

• Caspase pathway of elaidic acid (9t-C18:1)-induced apoptosis in human umbilical vein endothelial cells.

  Cell biology international 20120301

• Deleterious impact of elaidic fatty acid on ABCA1-mediated cholesterol efflux from mouse and human macrophages.

  Biochimica et biophysica acta 20120201

• Ecological-level associations between highly processed food intakes and plasma phospholipid elaidic acid concentrations: results from a cross-sectional study within the European prospective investigation into cancer and nutrition (EPIC).

  Nutrition and cancer 20111101

• [Terahertz spectroscopic investigation of elaidic acid].

  Guang pu xue yu guang pu fen xi = Guang pu 20111001

• Elaidic acid enhanced the simultaneous neurotoxicity attributable to the cerebral pathological lesion resulted from oxidative damages induced by acrylamide and benzo(a)pyrene.

  Toxicology and industrial health 20110801

• Determination of elaidic and vaccenic acids in foods using GC×GC-FID and GC×GC-TOFMS.

  Talanta 20110715

• Vaccenic and elaidic acid equally esterify into triacylglycerols, but differently into phospholipids of fed rat liver cells.

  Lipids 20110701

• Distinct effects of oleic acid and its trans-isomer elaidic acid on the expression of myokines and adipokines in cell models.

  The British journal of nutrition 20110401

• Enhanced role of elaidic acid on acrylamide-induced oxidative stress in epididymis and epididymal sperm that contributed to the impairment of spermatogenesis in mice.

  Toxicology and industrial health 20100901

• Elaidic acid sustains LPS and TNF-alpha induced ICAM-1 and VCAM-I expression on human bone marrow endothelial cells (HBMEC).

  Clinical biochemistry 20100801

• Dissimilar properties of vaccenic versus elaidic acid in beta-oxidation activities and gene regulation in rat liver cells.

  Lipids 20100701

• Delivery of 5-azacytidine to human cancer cells by elaidic acid esterification increases therapeutic drug efficacy.

  Molecular cancer therapeutics 20100501

• Vaccenic and elaidic acid modify plasma and splenocyte membrane phospholipids and mitogen-stimulated cytokine production in obese insulin resistant JCR: LA-cp rats.

  Nutrients 20100201

• Effect of trans unsaturation on molecular organization in a phospholipid membrane.

  Biochemistry 20091124

• Trans fat feeding results in higher serum alanine aminotransferase and increased insulin resistance compared with a standard murine high-fat diet.

  American journal of physiology. Gastrointestinal and liver physiology 20090801

• Metabolic implications of dietary trans-fatty acids.

  Obesity (Silver Spring, Md.) 20090601

• Correlation of erythrocyte fatty acid composition and dietary intakes with markers of atherosclerosis in patients with myocardial infarction.

  Nutrition research (New York, N.Y.) 20090601

• Modulation of rat neutrophil function in vitro by cis- and trans-MUFA.

  The British journal of nutrition 20090501

• Evaluation of fatty acid content of some Iranian fast foods with emphasis on trans fatty acids.

  Asia Pacific journal of clinical nutrition 20090101

• Association between serum trans-monounsaturated fatty acids and breast cancer risk in the E3N-EPIC Study.

  American journal of epidemiology 20080601

• 'Bottleneck effect' in two-dimensional microfluidics.

  Physical review letters 20080404

• Structure-effect relation of C18 long-chain fatty acids in the reduction of body weight in rats.

  International journal of obesity (2005) 20080301

• Phosphatidylcholine and sphingomyelin containing an elaidoyl fatty acid can form cholesterol-rich lateral domains in bilayer membranes.

  Biochimica et biophysica acta 20070701

• Activation of caspase 3 in HepG2 cells by elaidic acid (t18:1).

  Biochimica et biophysica acta 20070401

• Potentiation of TRPV3 channel function by unsaturated fatty acids.

  Journal of cellular physiology 20060701

• Sequentially combined estradiol valerate plus levonorgestrel therapy decreases 18:1 trans-fatty acid content of plasma lipids in healthy postmenopausal women.

  Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20051201

• Trans fatty acids induce apoptosis in human endothelial cells.

  Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20051201

• Low amounts of trans 18:1 fatty acids elevate plasma triacylglycerols but not cholesterol and alter the cellular defence to oxidative stress in mice.

  The British journal of nutrition 20050901

• Response of apolipoprotein E*3-Leiden transgenic mice to dietary fatty acids: combining liver proteomics with physiological data.

  FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050501

• Substrate dependence of the postischemic cardiomyocyte recovery: dissociation between functional, metabolic and injury markers.

  Molecular and cellular biochemistry 20050501

• Structures formed by the chiral assembly of racemic mixtures of enantiomers: iodination products of elaidic and oleic acids.

  The journal of physical chemistry. B 20050317

• Trans fatty acids alter the lipid composition and size of apoB-100-containing lipoproteins secreted by HepG2 cells.

  The Journal of nutritional biochemistry 20050301

• Leaky beta-oxidation of a trans-fatty acid: incomplete beta-oxidation of elaidic acid is due to the accumulation of 5-trans-tetradecenoyl-CoA and its hydrolysis and conversion to 5-trans-tetradecenoylcarnitine in the matrix of rat mitochondria.

  The Journal of biological chemistry 20041210

• Long-Term exposure of INS-1 cells to cis and trans fatty acids influences insulin release and fatty acid oxidation differentially.

  Metabolism: clinical and experimental 20040901

• Asp49 phospholipase A(2)-elaidoylamide complex: a new mode of inhibition.

  Biochemical and biophysical research communications 20040709

• Activation of latent transforming growth factor beta 1 and inhibition of matrix metalloprotease activity by a thrombospondin-like tripeptide linked to elaidic acid.

  Biochemical pharmacology 20040601

• Intracellular depletion of insulin: a comparative study with palmitate, oleate and elaidate in INS-1 cells.

  European journal of endocrinology 20030401

• Effects of oleic acid and its congeners, elaidic and stearic acids, on the structural properties of phosphatidylethanolamine membranes.

  Journal of lipid research 20030301

• Isomerization of stable isotopically labeled elaidic acid to cis and trans monoenes by ruminal microbes.

  Journal of lipid research 20021201

• Total synthesis and biological evaluation of (5Z,9Z)-5,9-hexadecadienoic acid, an inhibitor of human topoisomerase I.

  Journal of natural products 20021101

• Effects of diets enriched in saturated (palmitic), monounsaturated (oleic), or trans (elaidic) fatty acids on insulin sensitivity and substrate oxidation in healthy adults.

  Diabetes care 20020801

• Simple, intuitive calculations of free energy of binding for protein-ligand complexes. 1. Models without explicit constrained water.

  Journal of medicinal chemistry 20020606

• Acute effects of fatty acids on insulin secretion from rat and human islets of Langerhans.

  The Journal of endocrinology 20020401

• Oxidation of unsaturated fatty acids by human fibroblasts with very-long-chain acyl-CoA dehydrogenase deficiency: aspects of substrate specificity and correlation with clinical phenotype.

  Clinica chimica acta; international journal of clinical chemistry 20011001

• Lipids stimulate the production of 6-keto-prostaglandin f(1alpha) in human dorsal hand veins.

  Hypertension (Dallas, Tex. : 1979) 20011001

• Effect of dietary elaidic versus vaccenic acid on blood and liver lipids in the hamster.

  Atherosclerosis 20010701

• In vitro test for the effectiveness of antioxidants as inhibitors of thiyl radical-induced reactions with unsaturated fatty acids.

  Journal of agricultural and food chemistry 20010301

• Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.

  Antiviral research 20000301

• Fatty acids and derivatives as antimicrobial agents.

  Antimicrobial agents and chemotherapy 19720701