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10030-73-6,MFCD00067230
Catalog No.:AA0001GB

10030-73-6 | 9-Hexadecenoic acid, (9E)-

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100mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0001GB
Chemical Name:
9-Hexadecenoic acid, (9E)-
CAS Number:
10030-73-6
Molecular Formula:
C16H30O2
Molecular Weight:
254.4082
MDL Number:
MFCD00067230
SMILES:
CCCCCC/C=C/CCCCCCCC(=O)O
NSC Number:
277452
Properties
Computed Properties
 
Complexity:
209  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
13  
XLogP3:
6.4  

Downstream Synthesis Route
methylesterof/the/lower-melting9.10-dihydroxy-palmiticacid 
  373-49-9    10030-73-6 

[1]ChemischeBerichte,1941,vol.74,p.981

[1]ComptesRendusHebdomadairesdesSeancesdel'AcademiedesSciences,1945,vol.220,p.405    BulletindelaSocieteChimiquedeFrance,1946,p.90    Chem.Abstr.,1946,p.5398,5399

9-hexadecenoicacidmethylester 
  373-49-9    10030-73-6 

[1]Patent:WO2012/61093,2012,A1.Locationinpatent:Page/Pagecolumn25-26

Literature

Title: Biosynthesis and metabolic engineering of palmitoleate production, an important contributor to human health and sustainable industry.

Journal: Progress in lipid research 20121001

Title: Supplemental palmitoleic (C16:1 cis-9) acid reduces lipogenesis and desaturation in bovine adipocyte cultures.

Journal: Journal of animal science 20121001

Title: Lithocholic acid extends longevity of chronologically aging yeast only if added at certain critical periods of their lifespan.

Journal: Cell cycle (Georgetown, Tex.) 20120915

Title: High levels of stearic acid, palmitoleic acid, and dihomo-γ-linolenic acid and low levels of linoleic acid in serum cholesterol ester are associated with high insulin resistance.

Journal: Nutrition research (New York, N.Y.) 20120901

Title: Red blood cell membrane concentration of cis-palmitoleic and cis-vaccenic acids and risk of coronary heart disease.

Journal: The American journal of cardiology 20120815

Title: Palmitoleate is a mitogen, formed upon stimulation with growth factors, and converted to palmitoleoyl-phosphatidylinositol.

Journal: The Journal of biological chemistry 20120803

Title: Increased erythrocytes n-3 and n-6 polyunsaturated fatty acids is significantly associated with a lower prevalence of steatosis in patients with type 2 diabetes.

Journal: Clinical nutrition (Edinburgh, Scotland) 20120801

Title: Structural basis of Wnt recognition by Frizzled.

Journal: Science (New York, N.Y.) 20120706

Title: Gluteofemoral adipose tissue plays a major role in production of the lipokine palmitoleate in humans.

Journal: Diabetes 20120601

Title: Pharmacological evaluation of a novel cyclic phosphatidic acid derivative 3-S-cyclic phosphatidic acid (3-S-cPA).

Journal: Bioorganic & medicinal chemistry 20120515

Title: Knock-down of endothelial connexins impairs angiogenesis.

Journal: Pharmacological research 20120301

Title: Enzymatic activity and genetic variation in SCD1 modulate the relationship between fatty acids and inflammation.

Journal: Molecular genetics and metabolism 20120301

Title: Effects of diet and behavioral enrichment on free fatty acids in the aged canine brain.

Journal: Neuroscience 20120127

Title: Effect of fatty acids on the transdermal delivery of donepezil: in vitro and in vivo evaluation.

Journal: International journal of pharmaceutics 20120117

Title: Fatty acid composition of developing sea buckthorn (Hippophae rhamnoides L.) berry and the transcriptome of the mature seed.

Journal: PloS one 20120101

Title: Palmitoleate induces hepatic steatosis but suppresses liver inflammatory response in mice.

Journal: PloS one 20120101

Title: Rho signaling participates in membrane fluidity homeostasis.

Journal: PloS one 20120101

Title: Caenorhabditis elegans Delta12-desaturase FAT-2 is a bifunctional desaturase able to desaturate a diverse range of fatty acid substrates at the Delta12 and Delta15 positions.

Journal: The Journal of biological chemistry 20111223

Title: Cationic drug-derived nanoparticles for multifunctional delivery of anticancer siRNA.

Journal: Biomaterials 20111201

Title: Specific unsaturated fatty acids enforce the transdifferentiation of human cancer cells toward adipocyte-like cells.

Journal: Stem cell reviews 20111101

Title: Fatty acids identified in the Burmese python promote beneficial cardiac growth.

Journal: Science (New York, N.Y.) 20111028

Title: Redberry juniper as a roughage source in lamb feedlot rations: wool and carcass characteristics, meat fatty acid profiles, and sensory panel traits.

Journal: Meat science 20111001

Title: Efficient accumulation of oleic acid in Saccharomyces cerevisiae caused by expression of rat elongase 2 gene (rELO2) and its contribution to tolerance to alcohols.

Journal: Applied microbiology and biotechnology 20110901

Title: [Investigation of fatty acid profile for diagnostic purposes in mouse melanoma].

Journal: Magyar onkologia 20110901

Title: N-terminal residues of the Vibrio cholerae virulence regulatory protein ToxT involved in dimerization and modulation by fatty acids.

Journal: The Journal of biological chemistry 20110812

Title: Insulin sensitivity is not associated with palmitoleate availability in obese humans.

Journal: Journal of lipid research 20110401

Title: Relation between degree of obesity and site-specific adipose tissue fatty acid composition in a Mediterranean population.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20110201

Title: Dysregulation of Hnf1b gene expression in cultured beta-cells in response to cytotoxic fatty acid.

Journal: JOP : Journal of the pancreas 20110105

Title: Effects of perfluorinated fatty acids with different carbon chain length on fatty acid profiles of hepatic lipids in mice.

Journal: Biological & pharmaceutical bulletin 20110101

Title: Inhibitory effect of unsaturated fatty acids on saturated fatty acid-induced apoptosis in human pancreatic β-cells: activation of caspases and ER stress induction.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20110101

Title: Remodeling mitochondrial membranes during arousal from hibernation.

Journal: Physiological and biochemical zoology : PBZ 20110101

Title: Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2 diabetes.

Journal: Lipids in health and disease 20110101

Title: Regulation of lipid metabolism by palmitoleate and eicosapentaenoic acid (EPA) in mice fed a high-fat diet.

Journal: Bioscience, biotechnology, and biochemistry 20110101

Title: Summaries for patients. Dietary trans-palmitoleic acid and diabetes.

Journal: Annals of internal medicine 20101221

Title: Trans-palmitoleic acid, metabolic risk factors, and new-onset diabetes in U.S. adults: a cohort study.

Journal: Annals of internal medicine 20101221

Title: Structure-function analysis of human l-prostaglandin D synthase bound with fatty acid molecules.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20101201

Title: Effect of age and body weight of Greater Rhea (Rhea americana) females on egg number, size and composition.

Journal: British poultry science 20101201

Title: Regulation of podocyte survival and endoplasmic reticulum stress by fatty acids.

Journal: American journal of physiology. Renal physiology 20101001

Title: Optimal production of 7,10-dihydroxy-8(E)-hexadecenoic acid from palmitoleic acid by Pseudomonas aeruginosa PR3.

Journal: New biotechnology 20100930

Title: Pleiotropic effects of the goat prolactin receptor genotype on milk fatty acid composition.

Journal: Domestic animal endocrinology 20100801

Title: Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.

Journal: Archives of oral biology 20100801

Title: Modelling the influence of palmitic, palmitoleic, stearic and oleic acids on apparent heat resistance of spores of Bacillus cereus NTCC 11145 and Clostridium sporogenes Pasteur 79.3.

Journal: International journal of food microbiology 20100715

Title: [Palmitoleic acid and oleic acid].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20100701

Title: Lipomobilization in periparturient dairy cows influences the composition of plasma nonesterified fatty acids and leukocyte phospholipid fatty acids.

Journal: Journal of dairy science 20100601

Title: Dynamic changes in cytosolic and mitochondrial ATP levels in pancreatic acinar cells.

Journal: Gastroenterology 20100501

Title: Palmitoleate attenuates palmitate-induced Bim and PUMA up-regulation and hepatocyte lipoapoptosis.

Journal: Journal of hepatology 20100401

Title: Circulating palmitoleate strongly and independently predicts insulin sensitivity in humans.

Journal: Diabetes care 20100201

Title: Calorie restriction increases fatty acid synthesis and whole body fat oxidation rates.

Journal: American journal of physiology. Endocrinology and metabolism 20100101

Title: Loss of Stearoyl-CoA desaturase-1 attenuates adipocyte inflammation: effects of adipocyte-derived oleate.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20100101

Title: Effect of palmitoleic acid on melanogenic protein expression in murine b16 melanoma.

Journal: Journal of oleo science 20100101

Title: Different impacts of saturated and unsaturated free fatty acids on COX-2 expression in C(2)C(12) myotubes.

Journal: American journal of physiology. Endocrinology and metabolism 20091201

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: Pancreatic protease activation by alcohol metabolite depends on Ca2+ release via acid store IP3 receptors.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20090630

Title: Effects of dietary palmitoleic acid on plasma lipoprotein profile and aortic cholesterol accumulation are similar to those of other unsaturated fatty acids in the F1B golden Syrian hamster.

Journal: The Journal of nutrition 20090201

Title: Studies on chemical constituents of Gracilaria verrucosa.

Journal: Natural product research 20081201

Title: Loss of Ncb5or results in impaired fatty acid desaturation, lipoatrophy, and diabetes.

Journal: The Journal of biological chemistry 20081024

Title: Identification of a lipokine, a lipid hormone linking adipose tissue to systemic metabolism.

Journal: Cell 20080919

Title: Laboratory measurements of the heterogeneous oxidation of condensed-phase organic molecular makers for meat cooking emissions.

Journal: Environmental science & technology 20080715

Title: Plasma palmitoleic acid, a product of stearoyl-coA desaturase activity, is an independent marker of triglyceridemia and abdominal adiposity.

Journal: Nutrition, metabolism, and cardiovascular diseases : NMCD 20080701

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

Journal: American journal of epidemiology 20080601

Title: Differential regulation of the endoplasmic reticulum stress response in pancreatic beta-cells exposed to long-chain saturated and monounsaturated fatty acids.

Journal: The Journal of endocrinology 20080601

Title: In vivo role of lipid adducts on Wingless.

Journal: Journal of cell science 20080515

Title: Identification and functional expression of a Delta9-fatty acid desaturase from Psychrobacter urativorans in Escherichia coli.

Journal: Lipids 20080301

Title: Milk fatty acids II: prediction of the production of individual fatty acids in bovine milk.

Journal: Journal of dairy science 20080301

Title: Lipid characterization of a wrinkled sunflower mutant.

Journal: Phytochemistry 20080201

Title: Pathways of arachidonic acid peroxyl radical reactions and product formation with guanine radicals.

Journal: Chemical research in toxicology 20080201

Title: Region [corrected] of slowed conduction acts as core for spiral wave reentry in cardiac cell monolayers.

Journal: American journal of physiology. Heart and circulatory physiology 20080101

Title: Endothelial injury induces vascular smooth muscle cell proliferation in highly localized regions of a direct contact co-culture system.

Journal: Cell biochemistry and biophysics 20080101

Title: Association between fatty acid compositions and genotypes of FABP4 and LXR-alpha in Japanese black cattle.

Journal: BMC genetics 20080101

Title: Potassium loss is involved in tobacco cell death induced by palmitoleic acid and ceramide.

Journal: Archives of biochemistry and biophysics 20070901

Title: [Functional significance of lipid modification of secreted signaling proteins].

Journal: Seikagaku. The Journal of Japanese Biochemical Society 20070901

Title: Mechanisms involved in the cytotoxic and cytoprotective actions of saturated versus monounsaturated long-chain fatty acids in pancreatic beta-cells.

Journal: The Journal of endocrinology 20070801

Title: Production and identification of a novel compound, 7,10-dihydroxy-8(E)-hexadecenoic acid from palmitoleic acid by Pseudomonas aeruginosa PR3.

Journal: Applied microbiology and biotechnology 20070501

Title: Post-translational palmitoylation and glycosylation of Wnt-5a are necessary for its signalling.

Journal: The Biochemical journal 20070315

Title: Dipalmitoylation of radicicol results in improved efficacy against tumor growth and angiogenesis in vivo.

Journal: Cancer science 20070201

Title: Localization of lipids in the aortic wall with imaging TOF-SIMS.

Journal: Biochimica et biophysica acta 20070201

Title: Altered membrane free unsaturated fatty acid composition in human colorectal cancer tissue.

Journal: Molecular and cellular biochemistry 20070101

Title: Fatty acids and sleep in depressed inpatients.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20070101

Title: The sensitivity of yeast mutants to oleic acid implicates the peroxisome and other processes in membrane function.

Journal: Genetics 20070101

Title: Wnt lipid modifications: not as saturated as we thought.

Journal: Developmental cell 20061201

Title: Monounsaturated fatty acid modification of Wnt protein: its role in Wnt secretion.

Journal: Developmental cell 20061201

Title: Differential effects of palmitate and palmitoleate on insulin action and glucose utilization in rat L6 skeletal muscle cells.

Journal: The Biochemical journal 20061101

Title: Differential protective effects of palmitoleic acid and cAMP on caspase activation and cell viability in pancreatic beta-cells exposed to palmitate.

Journal: Apoptosis : an international journal on programmed cell death 20060701

Title: Construction and functional analysis of fatty acid desaturase gene disruptants in Candida albicans.

Journal: Microbiology (Reading, England) 20060501

Title: Ras and its signals diffuse through the cell on randomly moving nanoparticles.

Journal: Cancer research 20060215

Title: Protective effect of gap junction uncouplers given during hypoxia against reoxygenation injury in isolated rat hearts.

Journal: American journal of physiology. Heart and circulatory physiology 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: Micropatterns of propagation.

Journal: Advances in cardiology 20060101

Title: [Palmitoleic acid].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20050801

Title: Palmitoylation is a sorting determinant for transport to the myelin membrane.

Journal: Journal of cell science 20050601

Title: Changes in conjugated linoleic acid and palmitoleic acid are correlated to retinol levels in chronic renal failure in both hemodialysis and conservative treatment patients.

Journal: Artificial organs 20050501

Title: Evidence for cytochrome f involvement in eggplant cell death induced by palmitoleic acid.

Journal: Cell death and differentiation 20050401

Title: Evidence for signaling via gap junctions from smooth muscle to endothelial cells in rat mesenteric arteries: possible implication of a second messenger.

Journal: Cell calcium 20050401

Title: Lipid characterization of seed oils from high-palmitic, low-palmitoleic, and very high-stearic acid sunflower lines.

Journal: Lipids 20050401

Title: Serum lipid effects of a monounsaturated (palmitoleic) fatty acid-rich diet based on macadamia nuts in healthy, young Japanese women.

Journal: Clinical and experimental pharmacology & physiology 20041201

Title: Growth temperature affects accumulation of exogenous fatty acids and fatty acid composition in Schizosaccharomyces pombe.

Journal: Antonie van Leeuwenhoek 20041101

Title: Rat intestinal ceramidase: purification, properties, and physiological relevance.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20041001

Title: A palmitoylation switch mechanism in the regulation of the visual cycle.

Journal: Cell 20040611

Title: Two Delta9-stearic acid desaturases are required for Aspergillus nidulans growth and development.

Journal: Fungal genetics and biology : FG & B 20040501

Title: Biochemical characterization of a high-palmitoleic acid Helianthus annuus mutant.

Journal: Plant physiology and biochemistry : PPB 20040501

Title: Food and fatty acid intake and atopic disease in adults.

Journal: The European respiratory journal 20040401

Title: Regulation of stearoyl-CoA desaturases and role in metabolism.

Journal: Progress in lipid research 20040301

Title: Effect of fatty acids on the membrane potential of an alkaliphilic bacillus.

Journal: Current microbiology 20040301

Title: Mono-unsaturated fatty acids protect against beta-cell apoptosis induced by saturated fatty acids, serum withdrawal or cytokine exposure.

Journal: FEBS letters 20040227

Title: Antagonizing potencies of saturated and unsaturated long-chain free fatty acids to isoflurane in goldfish.

Journal: Journal of anesthesia 20040101

Title: Dietary conjugated linoleic acid differentially alters fatty acid composition and increases conjugated linoleic acid content in porcine adipose tissue.

Journal: The British journal of nutrition 20031101

Title: Conversion of alpha-linolenic acid to palmitic, palmitoleic, stearic and oleic acids in men and women.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20031001

Title: Effect of reduced maternal protein intake in pregnancy in the rat on the fatty acid composition of brain, liver, plasma, heart and lung phospholipids of the offspring after weaning.

Journal: The British journal of nutrition 20030801

Title: Fatty acid composition and productive traits of broiler fed diets containing conjugated linoleic acid.

Journal: Poultry science 20030801

Title: Alleviation of the cytotoxic activity induced by trans10, cis12-conjugated linoleic acid in rat hepatoma dRLh-84 cells by oleic or palmitoleic acid.

Journal: Cancer letters 20030710

Title: Monounsaturated fatty acids prevent the deleterious effects of palmitate and high glucose on human pancreatic beta-cell turnover and function.

Journal: Diabetes 20030301

Title: Comparison of the contents of the main biochemical compounds and the antioxidant activity of some Spanish olive oils as determined by four different radical scavenging tests.

Journal: The Journal of nutritional biochemistry 20030301

Title: Palmitoleic acid isomer (C16:1delta6) in human skin sebum is effective against gram-positive bacteria.

Journal: Skin pharmacology and applied skin physiology 20030101

Title: Different role of saturated and unsaturated fatty acids in beta-cell apoptosis.

Journal: Biochemical and biophysical research communications 20021220

Title: Fatty acid composition and preservation of the Tyrolean Iceman and other mummies.

Journal: Journal of lipid research 20021201

Title: The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women.

Journal: British journal of pharmacology 20020801

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

Journal: The Journal of endocrinology 20020401

Title: Effect of palmitoleic acid on bradykinin-induced endothelium-dependent relaxation in isolated pig ciliary artery.

Journal: Klinische Monatsblatter fur Augenheilkunde 20020401

Title: Metabolic fate and selective utilization of major fatty acids in human sebaceous gland.

Journal: The Journal of investigative dermatology 20020101

Title: [Fatty acids in the species of several zygomycete taxa].

Journal: Mikrobiologiia 20020101

Title: Aspects of the intercellular communication in aged hearts: effects of the gap junction uncoupler palmitoleic acid.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20011101

Title: Killing of Gram-positive cocci by fatty acids and monoglycerides.

Journal: APMIS : acta pathologica, microbiologica, et immunologica Scandinavica 20011001

Title: Transmembrane TNF (pro-TNF) is palmitoylated.

Journal: FEBS letters 20010629

Title: Lipase catalyzed synthesis of organic acid esters of lactic acid in non-aqueous media.

Journal: Journal of biotechnology 20010504

Title: Mitochondrial respiration on rumenic and linoleic acids.

Journal: Biochemical Society transactions 20010501

Title: The effect of low light flux and nitrogen deficiency on the chemical composition of Spirulina sp. (Arthrospira) grown on digested pig waste.

Journal: Bioresource technology 20010301

Title: Brain and hippocampus fatty acid composition in phospholipid classes of aged-relative cognitive deficit rats.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20010301

Title: Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3.

Journal: Archives of biochemistry and biophysics 20010301

Title: Distinct effects of saturated and monounsaturated fatty acids on beta-cell turnover and function.

Journal: Diabetes 20010101

Title: Frigolet ME, et al. The Role of the Novel Lipokine Palmitoleic Acid in Health and Disease.

Title: de Souza CO, et al. Palmitoleic Acid Improves Metabolic Functions in Fatty Liver by PPARα-Dependent AMPK Activation. J Cell Physiol. 2016 Dec 7. doi: 10.1002/jcp.25715.

Title: Yang ZH, et al. Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2 diabetes. Lipids Health Dis. 2011 Jul 21;10:120.

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Tags:10030-73-6 Molecular Formula|10030-73-6 MDL|10030-73-6 SMILES|10030-73-6 9-Hexadecenoic acid, (9E)-