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2420-56-6,MFCD02259040
Catalog No.:AA006X2P

2420-56-6 | (10E,12Z)-Octadeca-10,12-dienoic acid

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100g
80% (isomers mixture)
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500g
80% (isomers mixture)
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA006X2P
Chemical Name:
(10E,12Z)-Octadeca-10,12-dienoic acid
CAS Number:
2420-56-6
Molecular Formula:
C18H32O2
Molecular Weight:
280.4455
MDL Number:
MFCD02259040
SMILES:
CCCCC/C=C\C=C\CCCCCCCCC(=O)O
Properties
Computed Properties
 
Complexity:
267  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
14  
XLogP3:
7.1  

Literature

Title: Evaluation of anti-tubercular activity of linolenic acid and conjugated-linoleic acid as effective inhibitors against Mycobacterium tuberculosis.

Journal: Asian Pacific journal of tropical medicine 20160201

Title: Oleic acid attenuates trans-10,cis-12 conjugated linoleic acid-mediated inflammatory gene expression in human adipocytes.

Journal: Lipids 20121101

Title: The dietary fatty acid 10E12Z-CLA induces epiregulin expression through COX-2 dependent PGF(2α) synthesis in adipocytes.

Journal: Prostaglandins & other lipid mediators 20121001

Title: Acute exposure of L6 myotubes to cis-9, trans-11 and trans-10, cis-12 conjugated linoleic acid isomers stimulates glucose uptake by modulating Ca2+/calmodulin-dependent protein kinase II.

Journal: The international journal of biochemistry & cell biology 20120801

Title: Free radical scavenging activity of conjugated linoleic acid as single or mixed isomers.

Journal: Pharmaceutical biology 20120601

Title: Conjugated linoleic acid conversion by six Lactobacillus plantarum strains cultured in MRS broth supplemented with sunflower oil and soymilk.

Journal: Journal of food science 20120601

Title: 10e12z CLA alters adipocyte differentiation and adipocyte cytokine expression and induces macrophage proliferation.

Journal: The Journal of nutritional biochemistry 20120501

Title: The effect of strategic supplementation with trans-10,cis-12 conjugated linoleic acid on the milk production, estrous cycle characteristics, and reproductive performance of lactating dairy cattle.

Journal: Journal of dairy science 20120501

Title: Conjugated linoleic acid induces hepatic expression of fibroblast growth factor 21 through PPAR-α.

Journal: The British journal of nutrition 20120201

Title: High dose trans-10,cis-12 CLA increases lean body mass in hamsters, but elevates levels of plasma lipids and liver enzyme biomarkers.

Journal: Lipids 20120101

Title: Dietary CLA combined with palm oil or ovine fat differentially influences fatty acid deposition in tissues of obese Zucker rats.

Journal: Lipids 20120101

Title: Effect of a supplement containing trans-10,cis-12 conjugated linoleic acid on the performance of dairy ewes fed 2 levels of metabolizable protein and at a restricted energy intake.

Journal: Journal of dairy science 20120101

Title: De novo synthesis of trans-10, cis-12 conjugated linoleic acid in oleaginous yeast Yarrowia lipolytica.

Journal: Microbial cell factories 20120101

Title: Isomer-specific effects of conjugated linoleic acid on proliferative activity of cultured neural progenitor cells.

Journal: Molecular and cellular biochemistry 20111201

Title: Conjugated linoleic acid-induced apoptosis in mouse mammary tumor cells is mediated by both G protein coupled receptor-dependent activation of the AMP-activated protein kinase pathway and by oxidative stress.

Journal: Cellular signalling 20111201

Title: Characterization of the acute lactational response to trans-10, cis-12 conjugated linoleic acid.

Journal: Journal of dairy science 20111201

Title: Effect of trans-10 cis-12 conjugated linoleic acid on bovine oocyte competence and fatty acid composition.

Journal: Reproduction in domestic animals = Zuchthygiene 20111001

Title: JNK inhibition by SP600125 attenuates trans-10, cis-12 conjugated linoleic acid-mediated regulation of inflammatory and lipogenic gene expression.

Journal: Lipids 20111001

Title: Trans-10, cis-12 conjugated linoleic acid and the PPAR-γ agonist rosiglitazone attenuate lipopolysaccharide-induced TNF-α production by bovine immune cells.

Journal: Domestic animal endocrinology 20111001

Title: t10c12-CLA maintains higher bone mineral density during aging by modulating osteoclastogenesis and bone marrow adiposity.

Journal: Journal of cellular physiology 20110901

Title: The lipogenesis pathway as a cancer target.

Journal: Journal of medicinal chemistry 20110825

Title: Effect of trans-10, cis-12 conjugated linoleic acid on performance, adipose depot weights, and liver weight in early-lactation dairy cows.

Journal: Journal of dairy science 20110601

Title: Trans-10, cis-12-conjugated linoleic acid modulates NF-κB activation and TNF-α production in porcine peripheral blood mononuclear cells via a PPARγ-dependent pathway.

Journal: The British journal of nutrition 20110501

Title: Combined effects of trans-10,cis-12 conjugated linoleic acid, propionate, and acetate on milk fat yield and composition in dairy cows.

Journal: Journal of dairy science 20110401

Title: The change in conjugated linoleic acid concentration in blood of Japanese fed a conjugated linoleic acid diet.

Journal: Journal of nutritional science and vitaminology 20110101

Title: Trans-10, cis-12 conjugated linoleic acid inhibits skeletal muscle differentiation and GLUT4 expression independently from NF-κB activation.

Journal: Molecular nutrition & food research 20101201

Title: t10,c12-CLA decreases adiposity in peripubertal mice without dose-related detrimental effects on mammary development, inflammation status, and metabolism.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20101201

Title: Different mechanisms of cis-9,trans-11- and trans-10,cis-12- conjugated linoleic acid affecting lipid metabolism in 3T3-L1 cells.

Journal: The Journal of nutritional biochemistry 20101101

Title: Trans-10, cis-12 conjugated linoleic acid directly enhances the chemotactic activity of porcine peripheral blood polymorphonuclear neutrophillic leukocytes by activating F-actin polymerization in vitro.

Journal: Research in veterinary science 20101001

Title: Trans-10, cis-12-conjugated linoleic acid alters hepatic gene expression in a polygenic obese line of mice displaying hepatic lipidosis.

Journal: The Journal of nutritional biochemistry 20100901

Title: t10,c12-18:2-induced milk fat depression is less pronounced in cows fed high-concentrate diets.

Journal: Lipids 20100901

Title: Additive effects of trans-10, cis-12 conjugated linoleic acid and propionic acid on milk fat content and composition in dairy cows.

Journal: The Journal of dairy research 20100801

Title: trans-10,cis-12-Conjugated linoleic acid instigates inflammation in human adipocytes compared with preadipocytes.

Journal: The Journal of biological chemistry 20100604

Title: Differential effects of conjugated linoleic acid isomers in insulin-resistant female C57Bl/6J mice.

Journal: The Journal of nutritional biochemistry 20100401

Title: Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia.

Journal: Bioorganic & medicinal chemistry letters 20100315

Title: Serum adipokine profile and fatty acid composition of adipose tissues are affected by conjugated linoleic acid and saturated fat diets in obese Zucker rats.

Journal: The British journal of nutrition 20100301

Title: Acute oral safety study of dairy fat rich in trans-10 C18:1 versus vaccenic plus conjugated linoleic acid in rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100201

Title: Trans-10,cis-12-CLA dysregulate lipid and glucose metabolism and induce hepatic NR4A receptors.

Journal: Frontiers in bioscience (Elite edition) 20100101

Title: Trans-10,cis-12-CLA-caused lipodystrophy is associated with profound changes of fatty acid profiles of liver, white adipose tissue and erythrocytes in mice: possible link to tissue-specific alterations of fatty acid desaturation.

Journal: Annals of nutrition & metabolism 20100101

Title: Blood arachidonic acid and HDL cholesterol influence the phagocytic abilities of human monocytes/macrophages.

Journal: Annals of nutrition & metabolism 20100101

Title: Weak effect of trans-10, cis-12-conjugated linoleic acid on body fat accumulation in adult hamsters.

Journal: The British journal of nutrition 20091201

Title: Conjugated linoleic acid isomers, t10c12 and c9t11, are differentially incorporated into adipose tissue and skeletal muscle in humans.

Journal: Lipids 20091101

Title: Effects of intravenous infusion of trans-10, cis-12 18:2 on mammary lipid metabolism in lactating dairy cows.

Journal: Journal of dairy science 20091001

Title: Trans-10, cis-12-conjugated linoleic acid reduces the hepatic triacylglycerol content and the leptin mRNA level in adipose tissue in obese Zucker fa/fa rats.

Journal: The British journal of nutrition 20090901

Title: Trans-10, cis-12 conjugated linoleic acid modulates phagocytic responses of canine peripheral blood polymorphonuclear neutrophilic leukocytes exposed to Clostridium difficile toxin B.

Journal: Veterinary immunology and immunopathology 20090815

Title: A multi-gene analysis strategy identifies metabolic pathways targeted by trans-10, cis-12-conjugated linoleic acid in the liver of hamsters.

Journal: The British journal of nutrition 20090801

Title: [Effect of t10, c12-conjugated linoleic acid on fatty acid metabolism in C2C12 myotubes].

Journal: Wei sheng yan jiu = Journal of hygiene research 20090501

Title: Effect of calcium salts of a mixture of conjugated linoleic acids containing trans-10, cis-12 in the diet on milk fat synthesis in goats.

Journal: The British journal of nutrition 20090401

Title: Flaxseed oil prevents trans-10, cis-12-conjugated linoleic acid-induced insulin resistance in mice.

Journal: The British journal of nutrition 20090301

Title: Effects of trans-10,cis-12 conjugated linoleic acid on body composition in genetically obese mice.

Journal: Journal of medicinal food 20090201

Title: Hepatomegaly induced by trans-10,cis-12 conjugated linoleic acid in adult hamsters fed an atherogenic diet is not associated with steatosis.

Journal: Journal of the American College of Nutrition 20090201

Title: Conjugated linoleic acid isomers' roles in the regulation of PPAR-gamma and NF-kappaB DNA binding and subsequent expression of antioxidant enzymes in human umbilical vein endothelial cells.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20090101

Title: t10c12 conjugated linoleic acid suppresses HER2 protein and enhances apoptosis in SKBr3 breast cancer cells: possible role of COX2.

Journal: PloS one 20090101

Title: Trans-10, cis-12-conjugated linoleic acid does not increase body fat loss induced by energy restriction.

Journal: The British journal of nutrition 20081201

Title: Immunoenhancing effect of trans-10, cis-12 conjugated linoleic acid on the phagocytic capacity and oxidative burst activity of canine peripheral blood phagocytes.

Journal: Research in veterinary science 20081001

Title: A conjugated linoleic acid supplement containing trans-10, cis-12 conjugated linoleic acid reduces milk fat synthesis in lactating goats.

Journal: Journal of dairy science 20080901

Title: Biopsied and vitrified bovine embryos viability is improved by trans10, cis12 conjugated linoleic acid supplementation during in vitro embryo culture.

Journal: Animal reproduction science 20080701

Title: Apoptosis induced by t10,c12-conjugated linoleic acid is mediated by an atypical endoplasmic reticulum stress response.

Journal: Journal of lipid research 20080501

Title: t10,c12-Conjugated linoleic acid stimulates mammary tumor progression in Her2/ErbB2 mice through activation of both proliferative and survival pathways.

Journal: Carcinogenesis 20080501

Title: Conjugated linoleic acids differentially alter polyp number and diameter in the Apc(min/+) mouse model of intestinal cancer.

Journal: Cell proliferation 20080401

Title: Cytotoxic effects of the conjugated linoleic acid isomers t10c12, c9t11-CLA and mixed form on rat hepatic stellate cells and CCl4-induced hepatic fibrosis.

Journal: The Journal of nutritional biochemistry 20080301

Title: Conjugated linoleic acid isomers inhibit platelet-derived growth factor-induced NF-kappaB transactivation and collagen formation in human vascular smooth muscle cells.

Journal: European journal of nutrition 20080301

Title: Oleic acid prevents apoptotic cell death induced by trans10, cis12 isomer of conjugated linoleic acid via p38 MAP kinase dependent pathway.

Journal: In vitro cellular & developmental biology. Animal 20080101

Title: Adiposity and serum parameters in hamsters fed energy restricted diets supplemented or not with trans-10,cis-12 conjugated linoleic acid.

Journal: Journal of physiology and biochemistry 20071201

Title: Conjugated linoleic acid alters global gene expression in human intestinal-like Caco-2 cells in an isomer-specific manner.

Journal: The Journal of nutrition 20071101

Title: Influence of conjugated linoleic acid isomers on the metastasis of colon cancer cells in vitro and in vivo.

Journal: The Journal of nutritional biochemistry 20071001

Title: Antiobesity effect of trans-10,cis-12-conjugated linoleic acid-producing Lactobacillus plantarum PL62 on diet-induced obese mice.

Journal: Journal of applied microbiology 20071001

Title: Saturated fatty acid-mediated endoplasmic reticulum stress and apoptosis are augmented by trans-10, cis-12-conjugated linoleic acid in liver cells.

Journal: Molecular and cellular biochemistry 20070901

Title: Consumption of c9,t11-18:2 or t10,c12-18:2 enriched dietary supplements does not influence milk macronutrients in healthy, lactating women.

Journal: Lipids 20070901

Title: Evaluation of the mechanism of action of conjugated linoleic acid isomers on reproduction in dairy cows.

Journal: Journal of dairy science 20070901

Title: Quantitative gas chromatographic method for the analysis of cis-9, trans-11 and trans-10, cis-12 isomers of the conjugated linoleic acid in liver.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070815

Title: Effects of three different conjugated linoleic acid preparations on insulin signalling, fat oxidation and mitochondrial function in rats fed a high-fat diet.

Journal: The British journal of nutrition 20070801

Title: Heterologous expression of linoleic acid isomerase from Propionibacterium acnes and anti-proliferative activity of recombinant trans-10, cis-12 conjugated linoleic acid.

Journal: Microbiology (Reading, England) 20070801

Title: Effects of trans-10, cis-12 conjugated linoleic acid on ovine milk fat synthesis and cheese properties.

Journal: Journal of dairy science 20070701

Title: The t10,c12 isomer of conjugated linoleic acid stimulates mammary tumorigenesis in transgenic mice over-expressing erbB2 in the mammary epithelium.

Journal: Carcinogenesis 20070601

Title: Enhancement of ajoene-induced apoptosis by conjugated linoleic acid in 3T3-L1 adipocytes.

Journal: Apoptosis : an international journal on programmed cell death 20070601

Title: Effects of trans-10, cis-12 conjugated linoleic acid on the expression of uncoupling proteins in hamsters fed an atherogenic diet.

Journal: The British journal of nutrition 20070601

Title: Effects of trans-10,cis-12 conjugated linoleic acid on cholesterol metabolism in hypercholesterolaemic hamsters.

Journal: European journal of nutrition 20070601

Title: Leptin-induced matrix metalloproteinase-2 secretion is suppressed by trans-10,cis-12 conjugated linoleic acid.

Journal: Biochemical and biophysical research communications 20070518

Title: Cryosurvival of bovine blastocysts is enhanced by culture with trans-10 cis-12 conjugated linoleic acid (10t,12c CLA).

Journal: Animal reproduction science 20070401

Title: Conjugated linoleic acids promote human fat cell apoptosis.

Journal: Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20070301

Title: Upregulation of tumor necrosis factor-alpha expression by trans10-cis12 conjugated linoleic acid enhances phagocytosis of RAW macrophages via a peroxisome proliferator-activated receptor gamma-dependent pathway.

Journal: Cytokine 20070301

Title: Effects of a supplement containing trans-10, cis-12 conjugated linoleic acid on bioenergetic and milk production parameters in grazing dairy cows offered ad libitum or restricted pasture.

Journal: Journal of dairy science 20070201

Title: Dietary trans 10, cis 12-conjugated linoleic acid reduces the expression of fatty acid oxidation and drug detoxification enzymes in mouse liver.

Journal: The British journal of nutrition 20070101

Title: Trans-10, cis-12-conjugated linoleic acid increases phagocytosis of porcine peripheral blood polymorphonuclear cells in vitro.

Journal: The British journal of nutrition 20070101

Title: Upregulation of liver VLDL receptor and FAT/CD36 expression in LDLR-/- apoB100/100 mice fed trans-10,cis-12 conjugated linoleic acid.

Journal: Journal of lipid research 20061201

Title: Production of lean beef containing a high content of trans-10, cis-12 conjugated linoleic acid by feeding a high-temperature-micro-time-treated diet with extruded soybean.

Journal: Bioscience, biotechnology, and biochemistry 20061101

Title: Conjugated linoleic acid reduces phorbol ester-induced prostaglandin F2alpha production by bovine endometrial cells.

Journal: Journal of dairy science 20061001

Title: LDL receptor gene transcription is selectively induced by t10c12-CLA but not by c9t11-CLA in the human hepatoma cell line HepG2.

Journal: Biochimica et biophysica acta 20061001

Title: SREBP1 and thyroid hormone responsive spot 14 (S14) are involved in the regulation of bovine mammary lipid synthesis during diet-induced milk fat depression and treatment with CLA.

Journal: The Journal of nutrition 20061001

Title: The effects of t10,c12 CLA isomer compared with c9,t11 CLA isomer on lipid metabolism and body composition in hamsters.

Journal: The Journal of nutritional biochemistry 20060901

Title: Desaturation indices in liver, muscle, and bone of growing male and female mice fed trans-10,cis-12 conjugated linoleic acid.

Journal: Lipids 20060801

Title: Trans-10, trans-12 conjugated linoleic acid does not affect milk fat yield but reduces delta9-desaturase index in dairy cows.

Journal: Journal of dairy science 20060701

Title: Effects of trans-10,cis-12 conjugated linoleic acid on body fat and serum lipids in young and adult hamsters.

Journal: Journal of physiology and biochemistry 20060601

Title: A conjugated linoleic acid supplement containing trans-10, cis-12 reduces milk fat synthesis in lactating sheep.

Journal: Journal of dairy science 20060501

Title: Conjugated linoleic acid enhances transepithelial calcium transport in human intestinal-like Caco-2 cells: an insight into molecular changes.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20060501

Title: Chronic but not acute conjugated linoleic acid treatment inhibits deoxycholic acid-induced protein kinase C and nuclear factor-kappaB activation in human colorectal cancer cells.

Journal: European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20060401

Title: Effects of conjugated linoleic acid on linoleic and linolenic acid metabolism in man.

Journal: The British journal of nutrition 20060401

Title: trans-10,cis-12 conjugated linoleic acid prevents adiposity but not insulin resistance induced by an atherogenic diet in hamsters.

Journal: The Journal of nutritional biochemistry 20060201

Title: CLA isomers inhibit TNFalpha-induced eicosanoid release from human vascular smooth muscle cells via a PPARgamma ligand-like action.

Journal: Biochimica et biophysica acta 20060201

Title: Production of trans-10, cis-12 conjugated linoleic acid in rice.

Journal: Transgenic research 20060201

Title: Conjugated linoleic acid (CLA) up-regulates the estrogen-regulated cancer suppressor gene, protein tyrosine phosphatase gamma (PTPgama), in human breast cells.

Journal: Anticancer research 20060101

Title: Dietary trans-10, cis-12 and cis-9,trans-11 conjugated linoleic acids induce apoptosis in the colonic mucosa of rats treated with 1,2-dimethylhydrazine.

Journal: Journal of medicinal food 20060101

Title: Conjugated linoleic acid (CLA) modulates prostaglandin E2 (PGE2) signaling in canine mammary cells.

Journal: Anticancer research 20060101

Title: trans-10,cis-12 conjugated linoleic acid inhibits the G1-S cell cycle progression in DU145 human prostate carcinoma cells.

Journal: Journal of medicinal food 20060101

Title: Isomer-specific effect of conjugated linoleic acid on inflammatory adipokines associated with fat accumulation in 3T3-L1 adipocytes.

Journal: Journal of medicinal food 20060101

Title: Detection of conjugated dienoic fatty acids in human vascular smooth muscle cells treated with conjugated linoleic acid.

Journal: Biochimica et biophysica acta 20051215

Title: Cis-9,trans-11-CLA exerts anti-inflammatory effects in human bronchial epithelial cells and eosinophils: comparison to trans-10,cis-12-CLA and to linoleic acid.

Journal: Biochimica et biophysica acta 20051215

Title: Breast cancer cell-targeted oxidative stress: enhancement of cancer cell uptake of conjugated linoleic acid, activation of p53, and inhibition of proliferation.

Journal: Experimental and molecular pathology 20051001

Title: Divergent mechanisms of cis9, trans11-and trans10, cis12-conjugated linoleic acid affecting insulin resistance and inflammation in apolipoprotein E knockout mice: a proteomics approach.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20051001

Title: Isomer-specific regulation of differentiating pig preadipocytes by conjugated linoleic acids.

Journal: Journal of animal science 20050901

Title: Trans10, cis12-conjugated linoleic acid induces mitochondria-related apoptosis and lysosomal destabilization in rat hepatoma cells.

Journal: Biochimica et biophysica acta 20050815

Title: Functional genomic characterization of delipidation elicited by trans-10, cis-12-conjugated linoleic acid (t10c12-CLA) in a polygenic obese line of mice.

Journal: Physiological genomics 20050511

Title: Impaired lipid accumulation by trans10, cis12 CLA during adipocyte differentiation is dependent on timing and length of treatment.

Journal: Biochimica et biophysica acta 20050221

Title: Effects of human breast stromal cells on conjugated linoleic acid (CLA) modulated vascular endothelial growth factor-A (VEGF-A) expression in MCF-7 cells.

Journal: Anticancer research 20050101

Title: Supplementation with trans10cis12-conjugated linoleic acid induces hyperproinsulinaemia in obese men: close association with impaired insulin sensitivity.

Journal: Diabetologia 20040601

Title: Effects of specific conjugated linoleic acid isomers on growth characteristics in obese Zucker rats.

Journal: Lipids 20040601

Title: Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme.

Journal: Lipids 20030601

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Tags:2420-56-6 Molecular Formula|2420-56-6 MDL|2420-56-6 SMILES|2420-56-6 (10E,12Z)-Octadeca-10,12-dienoic acid