Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 10:26:52 -0600 |
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Update Date | 2015-10-02 02:25:50 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Caprylic acid |
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Description | Caprylic acid belongs to the class of Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain. (inferred from compound structure). Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. (WikiPedia). Caprylic acid is an intermediate in lipoate biosynthesis and incorporation II in E. coli. It is a substrate for lipoate-protein ligase A which catalyzes the chemical reaction a [lipoyl-carrier protein]-L-lysine + caprylic acid + ATP -> a [lipoyl-carrier protein] N6-octanoyl-L-lysine + AMP + diphosphate + H+. It is also a substrate for acyl-ACP synthetase in the reaction caprylic acid + a holo-[acyl-carrier protein] + ATP → an octanoyl-[acp] + AMP + diphosphate (EcoCyc compound: CPD-195). |
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Structure | |
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Synonyms: | - 1-Heptanecarboxylate
- 1-Heptanecarboxylic acid
- C-8 Acid
- Caprylate
- Caprylic acid
- Capryloate
- Capryloic acid
- Emery 657
- Kortacid 0899
- Lunac 8-95
- Lunac 8-98
- N-Caprylate
- N-Caprylic acid
- N-Octanoate
- N-Octanoic acid
- N-Octate
- N-Octic acid
- N-Octoate
- N-Octoic acid
- N-Octylate
- N-Octylic acid
- Neo-Fat 8
- Neo-Fat 8S
- Octanoate
- Octanoate (N-C8:0)
- Octanoic acid
- Octanoic acid (N-C8:0)
- Octoate
- Octoic acid
- Octylate
- Octylic acid
- Prifac 2901
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Chemical Formula: | C8H16O2 |
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Weight: | Average: 144.2114 Monoisotopic: 144.115029756 |
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InChI Key: | WWZKQHOCKIZLMA-UHFFFAOYSA-N |
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InChI: | InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) |
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CAS number: | 124-07-2 |
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IUPAC Name: | octanoic acid |
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Traditional IUPAC Name: | caprylic acid |
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SMILES: | CCCCCCCC(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-chain fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Liquid |
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Charge: | -1 |
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Melting point: | 16.5 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 0.789 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP: | 2.57 | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | |
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KEGG Pathways: | |
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EcoCyc Pathways: | - lipoate biosynthesis and incorporation II PWY0-1275
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0159-0910000000-e609d5de69ede6fbcde0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-0gb9-1920000000-1dc6ed976e003f99e23d | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-03kc-9000000000-74cfce03769b41313952 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0uyi-0931100000-7668e36e436054042b5c | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-0910000000-e609d5de69ede6fbcde0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0gb9-1920000000-1dc6ed976e003f99e23d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-0910000000-9ecb4ccb46e89710f76a | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0596-9100000000-8854c56056d8d3405087 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-062l-9100000000-67da39159980b9078fab | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0006-0900000000-bb237630bedcee6145d1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0006-2900000000-98284f50a271878c8481 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0006-5900000000-209fbbacd4996b9a770d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-03kc-9000000000-74cfce03769b41313952 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0006-0900000000-e2c4dff10393086340f7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0006-1900000000-bbde8564b4e5543a636a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negative | splash10-0006-0900000000-d219a0c6559a4783fd81 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-0900000000-e2c4dff10393086340f7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-1900000000-bbde8564b4e5543a636a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-0006-0900000000-ca22ecd0b25fa371fc73 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0gvp-9100000000-58c00a2024ba0bae4ff4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9300000000-2505e6738cf5d5877654 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-1ab4cdf8f74c93312743 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002b-2900000000-ac7c80e50c93b8cc3af7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9400000000-d2694b5f89d8eaeb2ab1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-f2b24072c91d8b0e4078 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-1900000000-ad62d44e72f4dd1760ab | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0007-7900000000-9c869b84815f21dffc7c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-b8a648d443695914e479 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a6u-9100000000-f5c38fdad70b324e75ac | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-bee103956686b4840d1e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-9000000000-e7cbd036c8e80018c825 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-8f2b048da6331570976c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0900000000-cd31ca01a5fa6be86acb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9100000000-682c215be5abe1fe87ed | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Dieterle F, Muller-Hagedorn S, Liebich HM, Gauglitz G: Urinary nucleosides as potential tumor markers evaluated by learning vector quantization. Artif Intell Med. 2003 Jul;28(3):265-79. Pubmed: 12927336
- Giannakou SA, Dallas PP, Rekkas DM, Choulis NH: In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. Int J Pharm. 2002 Jul 8;241(1):27-34. Pubmed: 12086718
- Habeeb AF, Francis RD: Preparation of human immunoglobulin by caprylic acid precipitation. Prep Biochem. 1984;14(1):1-17. Pubmed: 6718324
- Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- Nair MK, Joy J, Venkitanarayanan KS: Inactivation of Enterobacter sakazakii in reconstituted infant formula by monocaprylin. J Food Prot. 2004 Dec;67(12):2815-9. Pubmed: 15633694
- Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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Synthesis Reference: | Caprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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