Margaric acid, or heptadecanoic acid, is a saturated fatty acid. Its molecular formula is CH3(CH2)15CO2H. Classified as an odd-chain fatty acid, it occurs as a trace component of the fat and milkfat of ruminants. Salts and esters of margaric acid are called heptadecanoates.
Its name is derived from the Ancient Greek μάργαρος (márgar(on)), meaning "pearl(y)", due to its appearance.
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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) |
KEMQGTRYUADPNZ-UHFFFAOYSA-N |
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Chlamydomonas reinhardtii
(NCBI:txid3055)
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See:
PubMed
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Daphnia magna
(NCBI:txid35525)
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See:
Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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mammalian metabolite
Any animal metabolite produced during a metabolic reaction in mammals.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
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View more via ChEBI Ontology
17:0
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ChEBI
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C17:0
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ChEBI
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CH3‒[CH2]15‒COOH
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IUPAC
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heptadecoic acid
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ChEBI
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heptadecylic acid
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ChEBI
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margaric acid
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ChemIDplus
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margarinic acid
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NIST Chemistry WebBook
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Margarinsäure
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ChEBI
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n-heptadecanoic acid
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NIST Chemistry WebBook
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n-heptadecoic acid
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NIST Chemistry WebBook
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n-heptadecylic acid
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NIST Chemistry WebBook
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1781004
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Reaxys Registry Number
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Reaxys
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253195
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Gmelin Registry Number
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Gmelin
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506-12-7
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CAS Registry Number
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NIST Chemistry WebBook
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506-12-7
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CAS Registry Number
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ChemIDplus
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Benatar JR, Stewart RA (2014) The effects of changing dairy intake on trans and saturated fatty acid levels- results from a randomized controlled study. Nutrition journal 13, 32 [PubMed:24708591] [show Abstract]
BackgroundDairy food is an important natural source of saturated and trans fatty acids in the human diet. This study evaluates the effect of dietary advice to change dairy food intake on plasma fatty acid levels known to be present in milk in healthy volunteers.MethodsTwenty one samples of whole fat dairy milk were analyzed for fatty acids levels. Changes in levels of plasma phospholipid levels were evaluated in 180 healthy volunteers randomized to increase, not change or reduce dairy intake for one month. Fatty acids were measured by gas chromatography-mass spectrometry and levels are normalized to d-4 alanine.ResultsThe long chain fatty acids palmitic (13.4%), stearic (16.7%) and myristic (18.9%) acid were most common saturated fats in milk. Four trans fatty acids constituted 3.7% of the total milk fat content. Increased dairy food intake by 3.0 (± 1.2) serves/ day for 1 month was associated with small increases in plasma levels of myristic (+0.05, 95% confidence level-0.08 to 0.13, p = 0.07), pentadecanoic (+0.014, 95% confidence level -0.016 to 0.048, p = 0.02) and margaric acid (+0.02, -0.03 to 0.05, p = 0.03). There was no significant change in plasma levels of 4 saturated, 4 trans and 10 unsaturated fatty acids. Decreasing dairy food intake by 2.5 (± 1.2) serves per day was not associated with change in levels of any plasma fatty acid levels.ConclusionDietary advice to change dairy food has a minor effect on plasma fatty acid levels.Trial registrationACTRN12612000574842. | Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG (2007) Growth control of the eukaryote cell: a systems biology study in yeast. Journal of biology 6, 4 [PubMed:17439666] [show Abstract]
BackgroundCell growth underlies many key cellular and developmental processes, yet a limited number of studies have been carried out on cell-growth regulation. Comprehensive studies at the transcriptional, proteomic and metabolic levels under defined controlled conditions are currently lacking.ResultsMetabolic control analysis is being exploited in a systems biology study of the eukaryotic cell. Using chemostat culture, we have measured the impact of changes in flux (growth rate) on the transcriptome, proteome, endometabolome and exometabolome of the yeast Saccharomyces cerevisiae. Each functional genomic level shows clear growth-rate-associated trends and discriminates between carbon-sufficient and carbon-limited conditions. Genes consistently and significantly upregulated with increasing growth rate are frequently essential and encode evolutionarily conserved proteins of known function that participate in many protein-protein interactions. In contrast, more unknown, and fewer essential, genes are downregulated with increasing growth rate; their protein products rarely interact with one another. A large proportion of yeast genes under positive growth-rate control share orthologs with other eukaryotes, including humans. Significantly, transcription of genes encoding components of the TOR complex (a major controller of eukaryotic cell growth) is not subject to growth-rate regulation. Moreover, integrative studies reveal the extent and importance of post-transcriptional control, patterns of control of metabolic fluxes at the level of enzyme synthesis, and the relevance of specific enzymatic reactions in the control of metabolic fluxes during cell growth.ConclusionThis work constitutes a first comprehensive systems biology study on growth-rate control in the eukaryotic cell. The results have direct implications for advanced studies on cell growth, in vivo regulation of metabolic fluxes for comprehensive metabolic engineering, and for the design of genome-scale systems biology models of the eukaryotic cell. | COOKE NJ, HANSEN RP, SHORLAND FB (1957) Occurrence in butterfat of n-heptadecanoic acid (margaric acid). Nature 179, 98 [PubMed:13400103] | HANSEN RP, SHORLAND FB, COOKE NJ (1957) The occurrence of n-heptadecanoic acid (margaric acid) in unhydrogenated mutton fat. The Biochemical journal 65, 18-20 [PubMed:13403863] | MORICE IM, SHORLAND FB (1955) The isolation of n-pentadecanoic and n-heptadecanoic acids from shark (Galeorhincus australis Macleay) liver oil. The Biochemical journal 61, 453-456 [PubMed:13269382] |
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