1.0 2016-09-30 22:31:24 UTC 2020-06-04 21:59:04 UTC BMDB0000482 BMDB00482 Caprylic acid Caprylic acid, also known as 8:0 or octylic acid, 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. Caprylic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Caprylic acid exists in all living species, ranging from bacteria to humans. Caprylic acid participates in a number of enzymatic reactions, within cattle. In particular, Caprylic acid can be biosynthesized from trans-2-octenoic acid; which is mediated by the enzyme fatty acid synthase. enoyl reductase domain. In addition, Caprylic acid and malonic acid can be converted into 3-oxodecanoic acid through its interaction with the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, caprylic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Caprylic acid is a potentially toxic compound. 1-Heptanecarboxylic acid 8:0 Acide octanoique Acido octanoico Acidum octanocium Acidum octanoicum C8:0 CH3-[CH2]6-COOH Kaprylsaeure N-Caprylic acid N-Octanoic acid N-Octoic acid N-Octylic acid OCTANOIC ACID (caprylIC ACID) Octansaeure Octoic acid Octylic acid Octanoate 1-Heptanecarboxylate N-Caprylate N-Octanoate N-Octoate N-Octylate OCTANOate (caprylate) Octoate Octylate Octanoic acid Caprylate Emery 657 Kortacid 0899 Lunac 8-95 Lunac 8-98 Neo-fat 8 Neo-fat 8S Prifac 2901 Caprylic acid, cadmium salt Caprylic acid, cesium salt Caprylic acid, manganese salt Caprylic acid, nickel(+2) salt Caprylic acid, zinc salt Caprylic acid, aluminum salt Caprylic acid, barium salt Caprylic acid, chromium(+2) salt Caprylic acid, lead(+2) salt Caprylic acid, potassium salt Caprylic acid, tin(+2) salt Sodium octanoate Caprylic acid, 14C-labeled Caprylic acid, lithium salt Caprylic acid, ruthenium(+3) salt Caprylic acid, sodium salt Caprylic acid, sodium salt, 11C-labeled Caprylic acid, tin salt Caprylic acid, zirconium salt Sodium caprylate Caprylic acid, ammonia salt Caprylic acid, calcium salt Caprylic acid, cobalt salt Caprylic acid, copper salt Caprylic acid, copper(+2) salt Caprylic acid, iridum(+3) salt Caprylic acid, iron(+3) salt Caprylic acid, lanthanum(+3) salt Caprylic acid, zirconium(+4) salt FA(8:0) Lithium octanoate C8H16O2 144.2114 144.115029756 octanoic acid caprylic acid 124-07-2 CCCCCCCC(O)=O InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) WWZKQHOCKIZLMA-UHFFFAOYSA-N 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. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Medium-chain fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Aliphatic acyclic compounds Saturated fatty acids Straight chain fatty acids Straight chain fatty acids medium-chain fatty acid straight-chain saturated fatty acid Liquid melting_point 16.5 °C water_solubility 0.789 mg/mL logp 3.05 HANSCH,C ET AL. (1995) logp 2.92 ALOGPS logs -2.20 ALOGPS logp 2.7 ChemAxon pka_strongest_acidic 5.19 ChemAxon iupac octanoic acid ChemAxon average_mass 144.2114 ChemAxon mono_mass 144.115029756 ChemAxon smiles CCCCCCCC(O)=O ChemAxon formula C8H16O2 ChemAxon inchi InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) ChemAxon inchikey WWZKQHOCKIZLMA-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 40.28 ChemAxon polarizability 17.4 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Fatty Acid Biosynthesis SMP0087257 Specdb::NmrTwoD 1333 Specdb::MsIr 557 Specdb::MsIr 558 Specdb::MsIr 559 Specdb::EiMs 896 Specdb::CMs 557 Specdb::CMs 991 Specdb::CMs 2501 Specdb::CMs 29469 Specdb::CMs 30118 Specdb::CMs 30644 Specdb::CMs 31152 Specdb::CMs 31993 Specdb::CMs 37560 Specdb::CMs 162715 Specdb::CMs 1063271 Specdb::MsMs 698 Specdb::MsMs 699 Specdb::MsMs 700 Specdb::MsMs 4096 Specdb::MsMs 4097 Specdb::MsMs 4098 Specdb::MsMs 178293 Specdb::MsMs 178294 Specdb::MsMs 178295 Specdb::MsMs 180609 Specdb::MsMs 180610 Specdb::MsMs 180611 Specdb::MsMs 374162 Specdb::MsMs 437424 Specdb::MsMs 437425 Specdb::MsMs 438695 Specdb::MsMs 2244259 Specdb::MsMs 2245853 Specdb::MsMs 2246424 Specdb::MsMs 2697189 Specdb::MsMs 2697190 Specdb::MsMs 2697191 Specdb::MsMs 2981813 Specdb::MsMs 2981814 Specdb::MsMs 2981815 Specdb::NmrOneD 1389 Specdb::NmrOneD 2206 Specdb::NmrOneD 2900 Specdb::NmrOneD 4932 Specdb::NmrOneD 4933 Blood Detected by infra-red spectroscopy and silieic acid columns Laura Evans, Stuart Patton, R.D. McCarthy. Fatty Acid Composition of the Lipid Fractions from Bovine Serum Lipoproteins. J. Dairy Science (1961) 44(3) 475-482 doi: 10.3168/jds.S0022-0302(61)89765-8 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 10.5 +/- 0.4 uM Commercial skim milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 12.92 +/- 6.01 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 13.4 +/- 0.1 uM Commercial 1% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 1594.88 uM Milk, partly skim, conventional (not organic), 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1386.85 uM Milk, partly skim, organic, 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 277.371 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1317.51 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 10.2 +/- 0.2 uM Commercial 2% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 277.371 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 3397.79 uM Milk, whole, 3.5, (UHT), % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 3328.45 uM Milk, whole, conventional (not organic), 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 3120.42 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 8.8 +/- 0.1 uM Commercial 3.25% milk by LC–MS/MS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk Whole milk GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. 14168161 Milk Whole milk Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Milk 16 +/- 3 uM 1% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 11 +/- 2 uM 2% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 12 +/- 1 uM 3.25% milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 14.11 +/- 1.28 uM Free fatty acid in raw milk from a Danish Holstein herd by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk 14 +/- 4 uM Skim milk by NMR Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 12.83 +/- 2.57 uM Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk 3.85 +/- 0.77 uM Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk 4.11 +/- 1.026 uM Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk 12.9 +/- 0.02 uM Free fatty acid in raw milk by GC-MS Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203 Milk Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. 1779072 Milk 4853.999 +/- 2080.285 uM Raw milk Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. 16899705 Milk 17.682 +/- 0.42 uM Whole milk Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Milk 23.01 +/- 8.03 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 3536.485 +/- 832.114 uM The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Milk 3397.799 +/- 693.428 uM The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Milk Commercial, conventional whole milk Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X Milk 14.23 +/- 6.69 uM Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 Milk 0.8 (0.6 - 1.6) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 0.8 (0.6 - 1.4) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 0.8 (0.6 - 1.7) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Milk 5.6 (0.8 - 10.6) uM 3.5% Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C06423 370 FDB003336 DB04519 379 28837 C00001231 CPD-195 48223 Caprylic_acid 5469 Caprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp. Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. 16899705 Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. 11913692 Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. 1779072 Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. 20855010 GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. 14168161 O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. 29642378 van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. 28219465 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en BMDBP00368 Fatty acid synthase Q71SP7 FASN Enzyme