Nonadecylic acid, or nonadecanoic acid, is a 19-carbon saturated fatty acid with the chemical formula CH3(CH2)17COOH. It forms salts called nonadecylates. Nonadecylic acid can be found in fats and vegetable oils, although it is rare.
It is also present in the world of insects as the major constituent of the substance secreted by soldiers of the termite Rhinotermes marginalis for defence purposes.
Nonadecanoic acid has found applications in the field of metal lubrication.
The compound can be prepared by permanganate oxidation of 1-eicosene. |
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InChI=1S/C19H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21/h2-18H2,1H3,(H,20,21) |
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Ganoderma lucidum
(NCBI:txid5315)
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Found in
spore
(BTO:0001171).
See:
PubMed
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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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fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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View more via ChEBI Ontology
19:00
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ChEBI
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C19:0
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ChEBI
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n-nonadecanoic acid
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NIST Chemistry WebBook
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n-Nonadecanoic acid
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ChemIDplus
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nonadecylic acid
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ChEBI
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Nonadecylic acid
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KEGG COMPOUND
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1786261
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Reaxys Registry Number
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Reaxys
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646-30-0
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CAS Registry Number
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ChemIDplus
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646-30-0
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CAS Registry Number
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NIST Chemistry WebBook
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Fukuzawa M, Yamaguchi R, Hide I, Chen Z, Hirai Y, Sugimoto A, Yasuhara T, Nakata Y (2008) Possible involvement of long chain fatty acids in the spores of Ganoderma lucidum (Reishi Houshi) to its anti-tumor activity. Biological & pharmaceutical bulletin 31, 1933-1937 [PubMed:18827358] [show Abstract] During our isolation of biologically active substances from the spores of Ganoderma lucidum (Reishi Houshi, G. lucidum) guided by the inhibitory activity on HL-60 cell proliferation, NMR spectroscopic and mass spectrometric data indicate the substance contains a mixture of several long chain fatty acids. Hence, in this study, we have examined the inhibitory effects of an ethanolic extract of the spores of G. lucidum as the spore extract, on the proliferation of various human cancer cell lines by comparison with several authentic long chain fatty acids. Of the fatty acids we examined nonadecanoic acid (C19:0) showed the highest inhibitory activity for HL-60 cell proliferation with IC(50) values of 68+/-7 microM followed by heptadecanoic acid (C17:0, 120+/-23 microM), octa- (C18:0, 127+/-4 microM) and hexadecanoic acids (C16:0, 132+/-25 microM), respectively. The corresponding unsaturated fatty acids containing one double bond such as cis-10-nonadecenoic acid (C19:1), cis-9-octadecenoic acid (C18:1), cis-10-heptadecenoic acid (C17:1) and cis-9-hexadecenoic acid (C16:1) were less effective. The ethanolic extract of spores of G. lucidum were shown by annexin-V FITC/PI double staining to induce apoptosis of HL-60 cells in a similar way to cis-10-nonadecenoic acid (C19:1). These unsaturated fatty acids probably inhibit tumor necrosis factor production induced by lipopolysaccharide in a mouse macrophage preparation. Our results suggest the spores of G. lucidum contain 19-carbon fatty acids as one of the components for characteristics of its physiological effects. | Hadibarata T, Tachibana S, Itoh K (2007) Biodegradation of n-eicosane by fungi screened from nature. Pakistan journal of biological sciences : PJBS 10, 1804-1810 [PubMed:19086541] [show Abstract] The degradation of n-eicosane by Trichoderma sp. S019, a fungus collected from soil with extensive degradative ability on an agar medium containing n-eicosane, was demonstrated in liquid medium and in soil. Maximal degradation (77%) was obtained when Trichoderma sp. S019 was incubated for 30 days after the addition of 0.1 mM of n-eicosane to the liquid medium while the highest rate of degradation (40%) was obtained in soil with the addition of 1.5% Trichoderma sp. S019. Furthermore, the degradation of n-eicosane was affected by the addition of a carbon source, the addition of a nitrogen source and agitation. n-Eicosane was indeed degraded by Trichoderma sp. S019 because nonadecanoic acid, n-octadecane, hexadecanoic acid, oleic acid and stearic acid, considered to be the intermediates in the biodegradation of n-eicosane, were detected among the reaction products. |
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