200,000+ products from a single source!
sales@angenechem.com
Home > Other Building Blocks > 114818-04-1
114818-04-1 | 9,11-Octadecadienoic acid, 13-hydroxy-, (9E,11E,13S)-
CAS No: 114818-04-1 Catalog No: AG000FBD MDL No:
Product Description
Catalog Number:
AG000FBD
Chemical Name:
9,11-Octadecadienoic acid, 13-hydroxy-, (9E,11E,13S)-
CAS Number:
114818-04-1
Molecular Formula:
C18H32O3
Molecular Weight:
296.4449
IUPAC Name:
13-hydroxyoctadeca-9,11-dienoic acid
InChI:
InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)
InChI Key:
HNICUWMFWZBIFP-UHFFFAOYSA-N
SMILES:
CCCCC[C@@H](/C=C/C=C/CCCCCCCC(=O)O)O
Properties
Complexity:
295
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
296.235g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
296.451g/mol
Monoisotopic Mass:
296.235g/mol
Rotatable Bond Count:
14
Topological Polar Surface Area:
57.5A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
2
XLogP3:
5.3
Literature
| Title | Journal |
|---|---|
| Lowering dietary linoleic acid reduces bioactive oxidized linoleic acid metabolites in humans. | Prostaglandins, leukotrienes, and essential fatty acids 20121001 |
| Pioglitazone prevents smoking carcinogen-induced lung tumor development in mice. | Current cancer drug targets 20120701 |
| Relation of blood cadmium, lead, and mercury levels to biomarkers of lipid peroxidation in premenopausal women. | American journal of epidemiology 20120401 |
| Ligand-induced formation of transient dimers of mammalian 12/15-lipoxygenase: a key to allosteric behavior of this class of enzymes? | Proteins 20120301 |
| 15-Lipoxygenase-1 induces lipid peroxidation and apoptosis, and improves survival in rat malignant glioma. | In vivo (Athens, Greece) 20120101 |
| The cytochrome P450 inhibitor, ketoconazole, inhibits oxidized linoleic acid metabolite-mediated peripheral inflammatory pain. | Molecular pain 20120101 |
| Cyclooxygenases and lipoxygenases in cancer. | Cancer metastasis reviews 20111201 |
| 15-lipoxygenase-1 exerts its tumor suppressive role by inhibiting nuclear factor-kappa B via activation of PPAR gamma. | Journal of cellular biochemistry 20110901 |
| Epidermal FABP (FABP5) regulates keratinocyte differentiation by 13(S)-HODE-mediated activation of the NF-κB signaling pathway. | The Journal of investigative dermatology 20110301 |
| 5-lipoxygenase as an endogenous modulator of amyloid β formation in vivo. | Annals of neurology 20110101 |
| Cloning and characterization of a 9-lipoxygenase gene induced by pathogen attack from Nicotiana benthamiana for biotechnological application. | BMC biotechnology 20110101 |
| 13-hydroxy linoleic acid increases expression of the cholesterol transporters ABCA1, ABCG1 and SR-BI and stimulates apoA-I-dependent cholesterol efflux in RAW264.7 macrophages. | Lipids in health and disease 20110101 |
| Roles of peroxisome proliferator-activated receptor-alpha and -gamma in the development of non-small cell lung cancer. | American journal of respiratory cell and molecular biology 20101201 |
| L-4F differentially alters plasma levels of oxidized fatty acids resulting in more anti-inflammatory HDL in mice. | Drug metabolism letters 20100801 |
| Honokiol inhibits gastric tumourigenesis by activation of 15-lipoxygenase-1 and consequent inhibition of peroxisome proliferator-activated receptor-gamma and COX-2-dependent signals. | British journal of pharmacology 20100801 |
| Profiling lipoxygenase metabolism in specific steps of colorectal tumorigenesis. | Cancer prevention research (Philadelphia, Pa.) 20100701 |
| Ex vivo oxidation in tissue and plasma assays of hydroxyoctadecadienoates: Z,E/E,E stereoisomer ratios. | Chemical research in toxicology 20100517 |
| Identification of oxylipins with antifungal activity by LC-MS/MS from the supernatant of Pseudomonas 42A2. | Chemistry and physics of lipids 20100501 |
| 15-Lipoxygenases and its metabolites 15(S)-HETE and 13(S)-HODE in the development of non-small cell lung cancer. | Thorax 20100401 |
| 15-Lipoxygenase-1 expression suppresses the invasive properties of colorectal carcinoma cell lines HCT-116 and HT-29. | Cancer science 20091201 |
| Circadian stage-dependent inhibition of human breast cancer metabolism and growth by the nocturnal melatonin signal: consequences of its disruption by light at night in rats and women. | Integrative cancer therapies 20091201 |
| Effects of vitamin E on mitochondrial dysfunction and asthma features in an experimental allergic murine model. | Journal of applied physiology (Bethesda, Md. : 1985) 20091001 |
| Mechanistic investigations of human reticulocyte 15- and platelet 12-lipoxygenases with arachidonic acid. | Biochemistry 20090707 |
| Peroxisome proliferator-activated receptor gamma ligands isolated from adlay seed (Coix lacryma-jobi L. var. ma-yuen STAPF.). | Biological & pharmaceutical bulletin 20090401 |
| Synthesis and biological activity of hydroxylated derivatives of linoleic acid and conjugated linoleic acids. | Chemistry and physics of lipids 20090301 |
| Asymmetric dimethylarginine, oxidative stress, and vascular nitric oxide synthase in essential hypertension. | American journal of physiology. Regulatory, integrative and comparative physiology 20090201 |
| Human articular chondrocytes express 15-lipoxygenase-1 and -2: potential role in osteoarthritis. | Arthritis research & therapy 20090101 |
| Antiproliferative activity of guava leaf extract via inhibition of prostaglandin endoperoxide H synthase isoforms. | Prostaglandins, leukotrienes, and essential fatty acids 20090101 |
| Cross-Talk between PPARgamma and Insulin Signaling and Modulation of Insulin Sensitivity. | PPAR research 20090101 |
| Induction of arachidonate 12-lipoxygenase (Alox15) in intestine of iron-deficient rats correlates with the production of biologically active lipid mediators. | American journal of physiology. Gastrointestinal and liver physiology 20080401 |
| Asymmetric dimethylarginine and lipid peroxidation products in early autosomal dominant polycystic kidney disease. | American journal of kidney diseases : the official journal of the National Kidney Foundation 20080201 |
| Biomimetic nitration of the linoleic acid metabolite 13-hydroxyoctadecadienoic acid: isolation and spectral characterization of novel chain-rearranged epoxy nitro derivatives. | Chemistry and physics of lipids 20080101 |
| The 15-lipoxygenase-1 expression may enhance the sensitivity to non-steroidal anti-inflammatory drug-induced apoptosis in colorectal cancers from patients who are treated with the compounds. | Journal of gastroenterology and hepatology 20071201 |
| Dietary factors and growth and metabolism in experimental tumors. | The Journal of nutritional biochemistry 20071001 |
| [Activation mechanism of PPARgamma by its endogenous ligands]. | Seikagaku. The Journal of Japanese Biochemical Society 20071001 |
| 13-Oxo-ODE is an endogenous ligand for PPARgamma in human colonic epithelial cells. | Biochemical pharmacology 20070815 |
| Inhibition of fatty acid transport and proliferative activity in tissue-isolated human squamous cell cancer xenografts perfused in situ with melatonin or eicosapentaenoic or conjugated linoleic acids. | Comparative medicine 20070801 |
| The two faces of the 15-lipoxygenase in atherosclerosis. | Prostaglandins, leukotrienes, and essential fatty acids 20070801 |
| Evidence for oxylipin synthesis and induction of a new polyunsaturated fatty acid hydroxylase activity in Chondrus crispus in response to methyljasmonate. | Biochimica et biophysica acta 20070501 |
| The oxidative stress mediator 4-hydroxynonenal is an intracellular agonist of the nuclear receptor peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta). | Free radical biology & medicine 20070415 |
| Isoform-specific regulation of uridine diphosphate-glucuronosyltransferase 2B enzymes in the human prostate: differential consequences for androgen and bioactive lipid inactivation. | Endocrinology 20061101 |
| Metabolism of oxidized linoleic acid by glutathione transferases: peroxidase activity toward 13-hydroperoxyoctadecadienoic acid. | Biochimica et biophysica acta 20060701 |
| Differential modulation of cell cycle, apoptosis and PPARgamma2 gene expression by PPARgamma agonists ciglitazone and 9-hydroxyoctadecadienoic acid in monocytic cells. | Prostaglandins, leukotrienes, and essential fatty acids 20060501 |
| Oxidative metabolism of linoleic acid modulates PPAR-beta/delta suppression of PPAR-gamma activity. | Oncogene 20060223 |
| Dietary fish oil deactivates a growth-promoting signaling pathway in hepatoma 7288CTC in Buffalo rats. | Nutrition and cancer 20060101 |
| The critical role of 15-lipoxygenase-1 in colorectal epithelial cell terminal differentiation and tumorigenesis. | Cancer research 20051215 |
| Attenuation of breast tumor cell growth by conjugated linoleic acid via inhibition of 5-lipoxygenase activating protein. | Biochimica et biophysica acta 20051001 |
| Conjugated linoleic acid, cis-9,trans-11, is a substrate for pulmonary 15-lipoxygenase-1 in rat. | Journal of agricultural and food chemistry 20050907 |
| Overexpression of 15-lipoxygenase-1 induces growth arrest through phosphorylation of p53 in human colorectal cancer cells. | Molecular cancer research : MCR 20050901 |
| Tumor-associated down-regulation of 15-lipoxygenase-1 is reversed by celecoxib in colorectal cancer. | Annals of surgery 20050601 |
| Lipoxygenase-mediated metabolism of storage lipids in germinating sunflower cotyledons and beta-oxidation of (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid by the cotyledonary glyoxysomes. | Planta 20050401 |
| Free radical oxidation of coriolic acid (13-(S)-hydroxy-9Z,11E-octadecadienoic acid). | Chemistry and physics of lipids 20050401 |
| Characterization and quantification of free and esterified 9- and 13-hydroxyoctadecadienoic acids (HODE) in barley, germinating barley, and finished malt. | Journal of agricultural and food chemistry 20050309 |
| Glutathione peroxidase mimics as novel antioxidants from vegetables. | BioFactors (Oxford, England) 20050101 |
| The histone deacetylase inhibitor suberoylanilide hydroxamic acid induces apoptosis via induction of 15-lipoxygenase-1 in colorectal cancer cells. | Cancer research 20041201 |
| The novel pathway for ketodiene oxylipin biosynthesis in Jerusalem artichoke (Helianthus tuberosus) tubers. | Biochimica et biophysica acta 20041108 |
| Translocation of phospholipase A2 to membranes by oxidized LDL and hydroxyoctadecadienoic acid to contribute to cholesteryl ester formation. | Biochimica et biophysica acta 20041108 |
| 9HODE stimulates cell proliferation and extracellular matrix synthesis in human mesangial cells via PPARgamma. | Experimental biology and medicine (Maywood, N.J.) 20041101 |
| Autoxidative transformation of chiral omega6 hydroxy linoleic and arachidonic acids to chiral 4-hydroxy-2E-nonenal. | Chemical research in toxicology 20040701 |
| Differential inhibition of fatty acid transport in tissue-isolated steroid receptor negative human breast cancer xenografts perfused in situ with isomers of conjugated linoleic acid. | Cancer letters 20040608 |
| Melatonin uptake and growth prevention in rat hepatoma 7288CTC in response to dietary melatonin: melatonin receptor-mediated inhibition of tumor linoleic acid metabolism to the growth signaling molecule 13-hydroxyoctadecadienoic acid and the potential role of phytomelatonin. | Carcinogenesis 20040601 |
| Incorporation of arachidonic and linoleic acid hydroperoxides into cultured human umbilical vein endothelial cells. | Prostaglandins, leukotrienes, and essential fatty acids 20040601 |
| Enzymatically modified low-density lipoprotein upregulates CD36 in low-differentiated monocytic cells in a peroxisome proliferator-activated receptor-gamma-dependent way. | Biochemical pharmacology 20040301 |
| 15-Lipoxygenase-1 has anti-tumorigenic effects in colorectal cancer. | Prostaglandins, leukotrienes, and essential fatty acids 20040101 |
| Sensing environmental lipids by dendritic cell modulates its function. | Journal of immunology (Baltimore, Md. : 1950) 20040101 |
| Oxidized LDL activates phospholipase A2 to supply fatty acids required for cholesterol esterification. | Journal of lipid research 20030901 |
| Increased production of 12/15 lipoxygenase eicosanoids accelerates monocyte/endothelial interactions in diabetic db/db mice. | The Journal of biological chemistry 20030711 |
| Nonradiometric HPLC measurement of 13(S)-hydroxyoctadecadienoic acid from rat tissues. | Analytical biochemistry 20030701 |
| Platelet-type 12-lipoxygenase activates NF-kappaB in prostate cancer cells. | Prostaglandins & other lipid mediators 20030701 |
| Growth and fatty acid metabolism of human breast cancer (MCF-7) xenografts in nude rats: impact of constant light-induced nocturnal melatonin suppression. | Breast cancer research and treatment 20030601 |
| Evaluation of eicosanoids and NSAIDs as PPARgamma ligands in colorectal carcinoma cells. | Prostaglandins, leukotrienes, and essential fatty acids 20030501 |
| 15-Lipoxygenase-1 mediates cyclooxygenase-2 inhibitor-induced apoptosis in gastric cancer. | Carcinogenesis 20030201 |
| Association between E-cadherin expression by human colon, bladder and breast cancer cells and the 13-HODE:15-HETE ratio. A possible role of their metastatic potential. | Prostaglandins, leukotrienes, and essential fatty acids 20030101 |
| Opposing effects of 15-lipoxygenase-1 and -2 metabolites on MAPK signaling in prostate. Alteration in peroxisome proliferator-activated receptor gamma. | The Journal of biological chemistry 20021025 |
| Oleate and linoleate enhance the growth-promoting effects of insulin-like growth factor-I through a phospholipase D-dependent pathway in arterial smooth muscle cells. | The Journal of biological chemistry 20020927 |
| Modulation of epidermal tumor development caused by targeted overexpression of epidermis-type 12S-lipoxygenase. | Cancer research 20020815 |
| Metabolic profiling of oxylipins in germinating cucumber seedlings--lipoxygenase-dependent degradation of triacylglycerols and biosynthesis of volatile aldehydes. | Planta 20020801 |
| Dualism of oxidized lipoproteins in provoking and attenuating the oxidative burst in macrophages: role of peroxisome proliferator-activated receptor-gamma. | Journal of immunology (Baltimore, Md. : 1950) 20020315 |
| The activity of PPAR gamma in primary human trophoblasts is enhanced by oxidized lipids. | The Journal of clinical endocrinology and metabolism 20020301 |
| Dissociation of apoptosis induction and CD36 upregulation by enzymatically modified low-density lipoprotein in monocytic cells. | Biochemical and biophysical research communications 20020125 |
| Perturbation of lipid metabolism by linoleic acid hydroperoxide in CaCo-2 cells. | Biological chemistry 20020101 |
| Epidermal anti-Inflammatory properties of 5,11,14 20:3: effects on mouse ear edema, PGE2 levels in cultured keratinocytes, and PPAR activation. | Lipids in health and disease 20020101 |
| Overexpression of 15-lipoxygenase-1 in PC-3 human prostate cancer cells increases tumorigenesis. | Carcinogenesis 20011101 |
| 15-lipoxygenase-1 metabolites down-regulate peroxisome proliferator-activated receptor gamma via the MAPK signaling pathway. | The Journal of biological chemistry 20010914 |
| The orphan nuclear receptor small heterodimer partner as a novel coregulator of nuclear factor-kappa b in oxidized low density lipoprotein-treated macrophage cell line RAW 264.7. | The Journal of biological chemistry 20010907 |
| Troglitazone reduces the expression of PPARgamma while stimulating that of PPARalpha in mononuclear cells in obese subjects. | The Journal of clinical endocrinology and metabolism 20010701 |
| Nuclear factor-kappaB suppressive and inhibitor-kappaB stimulatory effects of troglitazone in obese patients with type 2 diabetes: evidence of an antiinflammatory action? | The Journal of clinical endocrinology and metabolism 20010701 |
| Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression. | Cancer research 20010615 |
| Human tear lipocalin acts as an oxidative-stress-induced scavenger of potentially harmful lipid peroxidation products in a cell culture system. | The Biochemical journal 20010515 |
| Binding of 13-HODE and 15-HETE to phospholipid bilayers, albumin, and intracellular fatty acid binding proteins. implications for transmembrane and intracellular transport and for protection from lipid peroxidation. | The Journal of biological chemistry 20010511 |
| 15-Deoxy-delta(12,14)-prostaglandin J(2) inhibits IL-10 and IL-12 production by macrophages. | Biochemical and biophysical research communications 20010504 |
| 13-hydroxy- and 13-oxooctadecadienoic acids: novel substrates for human UDP-glucuronosyltransferases. | Drug metabolism and disposition: the biological fate of chemicals 20010501 |
| The suppressive effect of dietary restriction and weight loss in the obese on the generation of reactive oxygen species by leukocytes, lipid peroxidation, and protein carbonylation. | The Journal of clinical endocrinology and metabolism 20010101 |
| Lipid peroxides induce expression of catalase in cultured vascular cells. | Journal of lipid research 20000801 |
| 15-LOX-1: a novel molecular target of nonsteroidal anti-inflammatory drug-induced apoptosis in colorectal cancer cells. | Journal of the National Cancer Institute 20000719 |
| Cytotoxic activity of 13-hydroxyoctadecadienoic acid against Toxoplasma gondii. | Parasitology 19921201 |
Related Products
Featured Products
© 2019 Angene International Limited. All rights Reserved.