Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H34O2 |
| Molecular Weight | 270.4507 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCCC(O)=O
InChI
InChIKey=KEMQGTRYUADPNZ-UHFFFAOYSA-N
InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
Margaric acid (Heptadecanoic acid, C17) is a fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid constitutes 0.61% of milk fat and 0.83% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. Margaric acid is a metabolite in glutamate and lipid metabolism in vivo. Blood-brain barrier permeable. Orally active. Possibly involved in anti-tumor activity.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| pex5 Mutants that differentially disrupt PTS1 and PTS2 peroxisomal matrix protein import in Arabidopsis. | 2010-12 |
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| Repercussion of a deficiency in mitochondrial ß-oxidation on the carbon flux of short-chain fatty acids to the peroxisomal ß-oxidation cycle in Aspergillus nidulans. | 2010-12 |
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| Uridine metabolism in HIV-1-infected patients: effect of infection, of antiretroviral therapy and of HIV-1/ART-associated lipodystrophy syndrome. | 2010-11-15 |
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| Neutrophil unsaturated fatty acid release by GM-CSF is impaired in cystic fibrosis. | 2010-11-08 |
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| Palmitate and insulin synergistically induce IL-6 expression in human monocytes. | 2010-11-05 |
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| Palmitoylation of the S0-S1 linker regulates cell surface expression of voltage- and calcium-activated potassium (BK) channels. | 2010-10-22 |
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| Antiobesity and antihyperglycemic effects of ginsenoside Rb1 in rats. | 2010-10 |
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| A conformation and orientation model of the carboxylic group of fatty acids dependent on chain length in a Langmuir monolayer film studied by polarization-modulation infrared reflection absorption spectroscopy. | 2010-09-09 |
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| Three Arabidopsis fatty acyl-coenzyme A reductases, FAR1, FAR4, and FAR5, generate primary fatty alcohols associated with suberin deposition. | 2010-08 |
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| Structural characterization of the major glycolipids from Arthrobacter globiformis and Arthrobacter scleromae. | 2010-07-02 |
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| Evolving neural network optimization of cholesteryl ester separation by reversed-phase HPLC. | 2010-07 |
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| Inhibition of stearoylCoA desaturase activity blocks cell cycle progression and induces programmed cell death in lung cancer cells. | 2010-06-30 |
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| [Classification of diabetes deficiency syndromes based on plasma fatty acid metabolic profilings using precolumn derivatization quantitative method]. | 2010-06 |
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| Increasing omega-3 desaturase expression in tomato results in altered aroma profile and enhanced resistance to cold stress. | 2010-06 |
|
| Cytosolic phospholipase A2alpha mediates Pseudomonas aeruginosa LPS-induced airway constriction of CFTR -/- mice. | 2010-04-29 |
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| Systems analysis of seed filling in Arabidopsis: using general linear modeling to assess concordance of transcript and protein expression. | 2010-04 |
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| The phosphate transporter PiT1 (Slc20a1) revealed as a new essential gene for mouse liver development. | 2010-02-10 |
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| Low-concentration ozone reacts with plasmalogen glycerophosphoethanolamine lipids in lung surfactant. | 2010-01 |
|
| Complete genome sequence of Stackebrandtia nassauensis type strain (LLR-40K-21). | 2009-12-30 |
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| Fatty acid synthase impacts the pathobiology of Candida parapsilosis in vitro and during mammalian infection. | 2009-12-22 |
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| A rapid and sensitive method for the simultaneous analysis of aliphatic and polar molecules containing free carboxyl groups in plant extracts by LC-MS/MS. | 2009-11-25 |
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| Antioxidant capacity of human milk and its association with vitamins A and E and fatty acid composition. | 2009-11 |
|
| Stability of metabolic correlations under changing environmental conditions in Escherichia coli--a systems approach. | 2009-10-15 |
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| Total synthesis and antileishmanial activity of the natural occurring acetylenic fatty acids 6-heptadecynoic acid and 6-icosynoic acid. | 2009-10 |
|
| Fat content and fatty acid compositions of 34 marine water fish species from the Mediterranean Sea. | 2009-09 |
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| Inhibition of stearoylCoA desaturase-1 inactivates acetyl-CoA carboxylase and impairs proliferation in cancer cells: role of AMPK. | 2009-08-27 |
|
| Unusual odd-chain and trans-octadecenoic fatty acids in tissues of feral European beaver (Castorfiber), Eurasian badger (Melesmeles) and raccoon dog (Nyctereutesprocyonoides). | 2009-06 |
|
| Effects of alpha-linolenic acid vs. docosahexaenoic acid supply on the distribution of fatty acids among the rat cardiac subcellular membranes after a short- or long-term dietary exposure. | 2009-03-25 |
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| Alkane inducible proteins in Geobacillus thermoleovorans B23. | 2009-03-25 |
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| Characterization of oxylipins and dioxygenase genes in the asexual fungus Aspergillus niger. | 2009-03-23 |
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| Synthetic LXR agonist attenuates plaque formation in apoE-/- mice without inducing liver steatosis and hypertriglyceridemia. | 2009-02 |
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| Identification of an endogenous ligand bound to a native orphan nuclear receptor. | 2009 |
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| Metabolomics of the interaction between PPAR-alpha and age in the PPAR-alpha-null mouse. | 2009 |
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| Peroxisome proliferator-activated receptor-gamma protects ERBB2-positive breast cancer cells from palmitate toxicity. | 2009 |
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| Preliminary evidence for cell membrane amelioration in children with cystic fibrosis by 5-MTHF and vitamin B12 supplementation: a single arm trial. | 2009 |
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| Metabolic profiling of the response to an oral glucose tolerance test detects subtle metabolic changes. | 2009 |
|
| Structure-activity relationship of immunostimulatory effects of phthalates. | 2008-10-31 |
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| Possible involvement of long chain fatty acids in the spores of Ganoderma lucidum (Reishi Houshi) to its anti-tumor activity. | 2008-10 |
|
| Integration of metabolomic and proteomic phenotypes: analysis of data covariance dissects starch and RFO metabolism from low and high temperature compensation response in Arabidopsis thaliana. | 2008-09 |
|
| Fatty acid profile of the erythrocyte membrane preceding development of Type 2 diabetes mellitus. | 2008-09 |
|
| A high throughput live transparent animal bioassay to identify non-toxic small molecules or genes that regulate vertebrate fat metabolism for obesity drug development. | 2008-08-27 |
|
| Polymorphism and solid-state miscibility in the pentadecanoic acid-heptadecanoic acid binary system. | 2008-07 |
|
| The "albumin effect" and in vitro-in vivo extrapolation: sequestration of long-chain unsaturated fatty acids enhances phenytoin hydroxylation by human liver microsomal and recombinant cytochrome P450 2C9. | 2008-05 |
|
| Plasmalogen levels in Gaucher disease. | 2008-02-22 |
|
| Metabolism of odd-numbered fatty acids and even-numbered fatty acids in mouse. | 2008 |
|
| Apicoplast lipoic acid protein ligase B is not essential for Plasmodium falciparum. | 2007-12 |
|
| Kurt Semm: A laparoscopic crusader. | 2007-01 |
|
| Demonstration of the thoracic duct by 123I heptadecanoic acid. Report of a case. | 1987-11-01 |
|
| Fast, low-temperature preparation of carrier-free 17-123I-heptadecanoic acid applied for liver and heart scintigraphy. | 1986 |
|
| Simultaneous determination by gas chromatography of the major metabolites in urine of toluene, xylenes and styrene. | 1978-02 |
Patents
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NCI_THESAURUS |
C68388
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NCI_THESAURUS |
C68421
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10465
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DTXSID5021596
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506-12-7
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Margaric acid
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1987137
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V987Y9OZ8L
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32365
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m7086
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300000054633
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208-027-1
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C68389
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3743
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SUBSTANCE RECORD
