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693-72-1,MFCD00002734
Catalog No.:AA003UWL

693-72-1 | Trans-11-octadecenoic acid

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50mg
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100mg
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500mg
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1g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003UWL
Chemical Name:
Trans-11-octadecenoic acid
CAS Number:
693-72-1
Molecular Formula:
C18H34O2
Molecular Weight:
282.4614
MDL Number:
MFCD00002734
SMILES:
CCCCCC/C=C/CCCCCCCCCC(=O)O
Properties
Properties
 
Form:
Liquid  
Storage:
Keep in dry area;-20 ℃;  

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  

Downstream Synthesis Route

[1]JournaloftheAmericanChemicalSociety,1948,vol.70,p.3393

Literature

Title: 10-Oxo-trans-11-octadecenoic acid generated from linoleic acid by a gut lactic acid bacterium Lactobacillus plantarum is cytoprotective against oxidative stress.

Journal: Toxicology and applied pharmacology 20160401

Title: Breed effect on quality veal production in mountain areas: emphasis on meat fatty acid composition.

Journal: Meat science 20121201

Title: Vaccenic acid in serum triglycerides is associated with markers of insulin resistance in men.

Journal: Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme 20121001

Title: Vaccenic acid-mediated reduction in cytokine production is independent of c9,t11-CLA in human peripheral blood mononuclear cells.

Journal: Biochimica et biophysica acta 20121001

Title: The intestinal bioavailability of vaccenic acid and activation of peroxisome proliferator-activated receptor-α and -γ in a rodent model of dyslipidemia and the metabolic syndrome.

Journal: Molecular nutrition & food research 20120801

Title: Conjugated linoleic acid synthesis-related protein proteasome subunit α 5 (PSMA5) is increased by vaccenic acid treatment in goat mammary tissue.

Journal: Journal of dairy science 20120801

Title: Red blood cell trans-18:1 isomeric profile correlates with subcutaneous fat and muscle profiles in beef cattle.

Journal: Meat science 20120601

Title: Effect of tanniniferous Terminalia chebula extract on rumen biohydrogenation, ∆(9)-desaturase activity, CLA content and fatty acid composition in longissimus dorsi muscle of kids.

Journal: Meat science 20120301

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

Journal: Biochimica et biophysica acta 20120201

Title: Ruminal microbe of biohydrogenation of trans-vaccenic acid to stearic acid in vitro.

Journal: BMC research notes 20120101

Title: Unique interplay between sugar and lipid in determining the antigenic potency of bacterial antigens for NKT cells.

Journal: PLoS biology 20111101

Title: Fatty acid composition in chronic heart failure: low circulating levels of eicosatetraenoic acid and high levels of vaccenic acid are associated with disease severity and mortality.

Journal: Journal of internal medicine 20110901

Title: Isomerization of vaccenic acid to cis and trans C18:1 isomers during biohydrogenation by rumen microbes.

Journal: Lipids 20110901

Title: A 4-week repeated oral dose toxicity study of dairy fat naturally enriched in vaccenic, rumenic and α-linolenic acids in rats.

Journal: Journal of agricultural and food chemistry 20110727

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

Journal: Talanta 20110715

Title: Inclusion of flaxseed in hay- and barley silage diets increases alpha-linolenic acid in cow plasma independent of forage type.

Journal: Lipids 20110701

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

Journal: Lipids 20110701

Title: Effects of ruminant trans fatty acids on cardiovascular disease and cancer: a comprehensive review of epidemiological, clinical, and mechanistic studies.

Journal: Advances in nutrition (Bethesda, Md.) 20110701

Title: Effect of ruminal pulse dose of polyunsaturated fatty acids on ruminal microbial populations and duodenal flow and milk profiles of fatty acids.

Journal: Journal of dairy science 20110601

Title: Fatty acid composition of ruminal bacteria and protozoa, and effect of defaunation on fatty acid profile in the rumen with special reference to conjugated linoleic acid in cattle.

Journal: Animal science journal = Nihon chikusan Gakkaiho 20110601

Title: Bovine milk fat enriched in conjugated linoleic and vaccenic acids attenuates allergic dermatitis in mice.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20110501

Title: Effects of fish oil and starch added to a diet containing sunflower-seed oil on dairy goat performance, milk fatty acid composition and in vivo delta9-desaturation of [13C]vaccenic acid.

Journal: The British journal of nutrition 20100801

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

Journal: Lipids 20100701

Title: Improving the fatty acid profile of dairy cow milk by combining grazing with feeding of total mixed ration.

Journal: The Journal of dairy research 20100501

Title: Proteomic analysis of endogenous conjugated linoleic acid biosynthesis in lactating rats and mouse mammary gland epithelia cells (HC11).

Journal: Biochimica et biophysica acta 20100401

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

Journal: Nutrients 20100201

Title: Effect of inoculated corn silage enriched with sunflower oil on rumen fermentation and lipid metabolism in an artificial rumen (RUSITEC).

Journal: Journal of the science of food and agriculture 20100115

Title: [Characteristics of the response of natural and recombinant luminescent microorganisms in the presence of Fe2+ ions].

Journal: Prikladnaia biokhimiia i mikrobiologiia 20100101

Title: A review of fatty acid profiles and antioxidant content in grass-fed and grain-fed beef.

Journal: Nutrition journal 20100101

Title: Effect of sampling fat location and cooking on fatty acid composition of beef steaks.

Journal: Meat science 20100101

Title: Prominent role of liver in elevated plasma palmitoleate levels in response to rosiglitazone in mice fed high-fat diet.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20091201

Title: Human health benefits of vaccenic acid.

Journal: Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme 20091001

Title: Vaccenic acid favourably alters immune function in obese JCR:LA-cp rats.

Journal: The British journal of nutrition 20090801

Title: Unusual odd-chain and trans-octadecenoic fatty acids in tissues of feral European beaver (Castorfiber), Eurasian badger (Melesmeles) and raccoon dog (Nyctereutesprocyonoides).

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20090601

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

Journal: The British journal of nutrition 20090501

Title: Selective production of cis-9,trans-11 isomer of conjugated linoleic acid from trans-vaccenic acid methyl ester by Delacroixia coronata.

Journal: Journal of applied microbiology 20090501

Title: Mechanism of conjugated linoleic acid and vaccenic acid formation in human faecal suspensions and pure cultures of intestinal bacteria.

Journal: Microbiology (Reading, England) 20090101

Title: Studies on the production of conjugated linoleic acid from linoleic and vaccenic acids by mixed rumen protozoa.

Journal: Applied microbiology and biotechnology 20081201

Title: Short communication: malic acid does not promote vaccenic acid accumulation in mixed ruminal fluid with fractionated fish oil by a rumen-simulation technique.

Journal: Journal of dairy science 20081001

Title: The effect of dietary inclusion of olive tree leaves and grape marc on the content of conjugated linoleic acid and vaccenic acid in the milk of dairy sheep and goats.

Journal: The Journal of dairy research 20080801

Title: Cis-9, trans-11-conjugated linoleic acid but not its precursor trans-vaccenic acid attenuate inflammatory markers in the human colonic epithelial cell line Caco-2.

Journal: The British journal of nutrition 20080701

Title: Feeding soybean oil to dairy goats increases conjugated linoleic acid in milk.

Journal: Journal of dairy science 20080601

Title: Bovine milk fat enriched in conjugated linoleic and vaccenic acids attenuates allergic airway disease in mice.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20080101

Title: Effects of butter naturally enriched with conjugated linoleic acid and vaccenic acid on blood lipids and LDL particle size in growing pigs.

Journal: Lipids in health and disease 20080101

Title: Vaccenic acid and cis-9,trans-11 CLA in the rumen and different tissues of pasture- and concentrate-fed beef cattle.

Journal: Lipids 20071201

Title: Trans fats, dyslipidemia and the metabolic syndrome: are we missing the cream?

Journal: The Canadian nurse 20071101

Title: Biohydrogenation of linoleic acid by rumen fungi compared with rumen bacteria.

Journal: Journal of applied microbiology 20070901

Title: Diet supplementation with fish oil and sunflower oil to increase conjugated linoleic acid levels in milk fat of partially grazing dairy cows.

Journal: Journal of dairy science 20070601

Title: Factors influencing biohydrogenation and conjugated linoleic acid production by mixed rumen fungi.

Journal: Journal of microbiology (Seoul, Korea) 20070601

Title: Fatty acid composition of ruminal bacteria and protozoa, with emphasis on conjugated linoleic acid, vaccenic acid, and odd-chain and branched-chain fatty acids.

Journal: Journal of animal science 20070501

Title: Influence of organic diet on the amount of conjugated linoleic acids in breast milk of lactating women in the Netherlands.

Journal: The British journal of nutrition 20070401

Title: Structures and physiological roles of 13 integral lipids of bovine heart cytochrome c oxidase.

Journal: The EMBO journal 20070321

Title: Kinetics of fatty acid biohydrogenation in vitro.

Journal: Journal of dairy science 20070301

Title: The effect of solids dilution rate and oil source on trans C18:1 and conjugated linoleic acid production by ruminal microbes in continuous culture.

Journal: Journal of dairy science 20070201

Title: Effectiveness of oils rich in linoleic and linolenic acids to enhance conjugated linoleic acid in milk from dairy cows.

Journal: Journal of dairy science 20070201

Title: Short communication: Eicosatrienoic acid and docosatrienoic acid do not promote vaccenic acid accumulation in mixed ruminal cultures.

Journal: Journal of dairy science 20061101

Title: Contribution of rumen protozoa to duodenal flow of nitrogen, conjugated linoleic acid and vaccenic acid in steers fed silages differing in their water-soluble carbohydrate content.

Journal: The British journal of nutrition 20061101

Title: Milk production and composition from cows fed small amounts of fish oil with extruded soybeans.

Journal: Journal of dairy science 20061001

Title: Rumen ciliate protozoa contain high concentrations of conjugated linoleic acids and vaccenic acid, yet do not hydrogenate linoleic acid or desaturate stearic acid.

Journal: The British journal of nutrition 20061001

Title: The membrane bound bacterial lipocalin Blc is a functional dimer with binding preference for lysophospholipids.

Journal: FEBS letters 20060904

Title: Comparing the fatty acid composition of organic and conventional milk.

Journal: Journal of dairy science 20060601

Title: Eicosapentaenoic acid and 3,10 dithia stearic acid inhibit the desaturation of trans-vaccenic acid into cis-9, trans-11-conjugated linoleic acid through different pathways in Caco-2 and T84 cells.

Journal: The British journal of nutrition 20060401

Title: Trans-11-18 : 1 is effectively Delta9-desaturated compared with trans-12-18 : 1 in humans.

Journal: The British journal of nutrition 20060401

Title: Augmentation of vaccenate production and suppression of vaccenate biohydrogenation in cultures of mixed ruminal microbes.

Journal: Journal of dairy science 20060301

Title: Effect of dietary vitamin E on rumen biohydrogenation pathways and milk fat depression in dairy cows fed high-fat diets.

Journal: Journal of dairy science 20060201

Title: The influence of n-3 polyunsaturated fatty acids and very low calorie diet during a short-term weight reducing regimen on weight loss and serum fatty acid composition in severely obese women.

Journal: Physiological research 20060101

Title: Milk and cheese from cows fed calcium salts of palm and fish oil alone or in combination with soybean products.

Journal: Journal of dairy science 20060101

Title: Supplementation with extruded linseed cake affects concentrations of conjugated linoleic acid and vaccenic acid in goat milk.

Journal: Journal of dairy science 20060101

Title: Biohydrogenation of fatty acids and digestibility of fresh alfalfa or alfalfa hay plus sucrose in continuous culture.

Journal: Journal of dairy science 20051101

Title: Milk and cheese fatty acid composition in sheep fed Mediterranean forages with reference to conjugated linoleic acid cis-9,trans-11.

Journal: Journal of dairy science 20051001

Title: Incorporation of cis-9, trans-11 conjugated linoleic acid and vaccenic acid (trans-11 18 : 1) into plasma and leucocyte lipids in healthy men consuming dairy products naturally enriched in these fatty acids.

Journal: The British journal of nutrition 20050801

Title: Seasonal variation in conjugated linoleic acid and vaccenic acid in milk fat of sheep and its transfer to cheese and ricotta.

Journal: Journal of dairy science 20050401

Title: Vaccenic acid metabolism in the liver of rat and bovine.

Journal: Lipids 20050301

Title: Vaccenic and rumenic acids, a distinct feature of ruminant fats.

Journal: Journal of dairy science 20050201

Title: Flavor and stability of pasteurized milk with elevated levels of conjugated linoleic acid and vaccenic acid.

Journal: Journal of dairy science 20050201

Title: Drosophila OBP LUSH is required for activity of pheromone-sensitive neurons.

Journal: Neuron 20050120

Title: GC-MS structural characterization of fatty acids from marine aerobic anoxygenic phototrophic bacteria.

Journal: Lipids 20050101

Title: Conjugated linoleic acid increases in milk when cows fed fish meal and extruded soybeans for an extended period of time.

Journal: Journal of dairy science 20040601

Title: Plea for using the term n-7 fatty acids in place of C18:2 cis-9, trans-11, and C18:1 trans-11 or their trivial names rumenic acid and vaccenic acid rather than the generic term conjugated linoleic acids.

Journal: Journal of dairy science 20040501

Title: Short communication: docosahexaenoic acid promotes vaccenic acid accumulation in mixed ruminal cultures when incubated with linoleic acid.

Journal: Journal of dairy science 20040401

Title: Endogenous synthesis of cis-9, trans-11 conjugated linoleic acid in dairy cows fed fresh pasture.

Journal: Journal of dairy science 20040201

Title: Effects of dietary cis 9, trans 11-18:2, trans 10, cis 12-18:2, or vaccenic acid (trans 11-18:1) during lactation on body composition, tissue fatty acid profiles, and litter growth in mice.

Journal: The British journal of nutrition 20031201

Title: Conjugated linoleic acid and vaccenic acid in rumen, plasma, and milk of cows fed fish oil and fats differing in saturation of 18 carbon fatty acids.

Journal: Journal of dairy science 20031101

Title: Might analysis, synthesis and metabolism of CLA contribute to explain the biological effects of CLA?

Journal: European journal of medical research 20030820

Title: Vaccenic acid (t11-18:1) is converted to c9,t11-CLA in MCF-7 and SW480 cancer cells.

Journal: Lipids 20030601

Title: Fresh forage and solin supplementation on conjugated linoleic acid levels in plasma and milk.

Journal: Journal of dairy science 20030501

Title: Milk conjugated linoleic acid response to fish oil supplementation of diets differing in fatty acid profiles.

Journal: Journal of dairy science 20030301

Title: Fatty acid profiles of milk and rumen digesta from cows fed fish oil, extruded soybeans or their blend.

Journal: Journal of dairy science 20020901

Title: Regiospecific enzymatic oxygenation of cis-vaccenic acid during aerobic senescence of the halophilic purple sulfur bacterium Thiohalocapsa halophila.

Journal: Lipids 20020601

Title: Feeding fish meal and extruded soybeans enhances the conjugated linoleic acid (CLA) content of milk.

Journal: Journal of dairy science 20020301

Title: (13)C NMR characterization of triacylglycerols of Moringa oleifera seed oil: an 'oleic-vaccenic acid' oil.

Journal: Journal of agricultural and food chemistry 20020227

Title: Dibutyrate derivatization of monoacylglycerols for the resolution of regioisomers of oleic, petroselinic, and cis-vaccenic acids.

Journal: Lipids 20020101

Title: Dietary trans-vaccenic acid (trans11-18:1) increases concentration of cis9,transll-conjugated linoleic acid (rumenic acid) in tissues of lactating mice and suckling pups.

Journal: Reproduction, nutrition, development 20020101

Title: Modulation of lipid metabolism and vitamin A by conjugated linoleic acid.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20020101

Title: 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.

Journal: Clinica chimica acta; international journal of clinical chemistry 20011001

Title: Effect of forage:concentrate ratio on ruminal digestion and duodenal flow of fatty acids in ewes.

Journal: Journal of animal science 20010801

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

Journal: Atherosclerosis 20010701

Title: Training affects muscle phospholipid fatty acid composition in humans.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 20010201

Title: Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland.

Journal: Nutrition and cancer 20010101

Title: Li D, et al. Ruminal microbe of biohydrogenation of trans-vaccenic acid to stearic acid in vitro. BMC Res Notes. 2012 Feb 15;5:97.

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SDS
Tags:693-72-1 Molecular Formula|693-72-1 MDL|693-72-1 SMILES|693-72-1 Trans-11-octadecenoic acid