1.0 2016-09-30 22:26:56 UTC 2020-06-04 22:58:27 UTC BMDB0000220 BMDB00220 Palmitic acid Palmitic acid, also known as C16 or palmitate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Palmitic acid exists in all living species, ranging from bacteria to humans. Palmitic acid is a potentially toxic compound. 1-Hexyldecanoic acid 1-Pentadecanecarboxylic acid 16:00 C16 C16 Fatty acid C16:0 Cetylic acid CH3-[CH2]14-COOH FA 16:0 Hexadecanoate Hexadecoic acid Hexadecylic acid Hexaectylic acid N-Hexadecanoic acid N-Hexadecoic acid Palmitate Palmitinic acid Palmitinsaeure Pentadecanecarboxylic acid 1-Hexyldecanoate 1-Pentadecanecarboxylate Cetylate Hexadecanoic acid Hexadecoate Hexadecylate Hexaectylate N-Hexadecanoate N-Hexadecoate Palmitinate Pentadecanecarboxylate Acid, hexadecanoic Acid, palmitic Edenor C16 Emersol 140 Emersol 143 Glycon P-45 Hexadecanoate (N-C16:0) Hexadecanoic acid palmitic acid Hydrofol Hydrofol acid 1690 Hystrene 8016 Hystrene 9016 Industrene 4516 Kortacid 1698 Loxiol ep 278 Lunac P 95 Lunac P 95KC Lunac P 98 Palmitoate Palmitoic acid PAM PLM Prifac 2960 Prifrac 2960 Pristerene 4934 Univol u332 FA(16:0) C16H32O2 256.4241 256.240230268 hexadecanoic acid palmitic acid 57-10-3 CCCCCCCCCCCCCCCC(O)=O InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) IPCSVZSSVZVIGE-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Long-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 Long-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 long-chain fatty acid straight-chain saturated fatty acid Solid melting_point 61.8 °C water_solubility 4e-05 mg/mL logp 7.17 SANGSTER (1993) logp 7.23 ALOGPS logs -5.80 ALOGPS logp 6.26 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac hexadecanoic acid ChemAxon average_mass 256.4241 ChemAxon mono_mass 256.240230268 ChemAxon smiles CCCCCCCCCCCCCCCC(O)=O ChemAxon formula C16H32O2 ChemAxon inchi InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) ChemAxon inchikey IPCSVZSSVZVIGE-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 77.08 ChemAxon polarizability 34.36 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Bile Acid Biosynthesis SMP0087236 Fatty Acid Biosynthesis SMP0087257 Fatty Acid Elongation in Mitochondria SMP0087194 Fatty Acid Metabolism SMP0087172 Glycerolipid Metabolism SMP0087230 Steroid Biosynthesis SMP0087233 Specdb::NmrTwoD 1216 Specdb::CMs 475 Specdb::CMs 476 Specdb::CMs 1756 Specdb::CMs 3263 Specdb::CMs 28247 Specdb::CMs 30396 Specdb::CMs 30904 Specdb::CMs 31084 Specdb::CMs 31676 Specdb::CMs 31949 Specdb::CMs 37367 Specdb::CMs 160275 Specdb::CMs 1055058 Specdb::EiMs 1128 Specdb::NmrOneD 1217 Specdb::NmrOneD 3179 Specdb::NmrOneD 4752 Specdb::NmrOneD 4753 Specdb::MsMs 358 Specdb::MsMs 359 Specdb::MsMs 360 Specdb::MsMs 3663 Specdb::MsMs 20117 Specdb::MsMs 20118 Specdb::MsMs 20119 Specdb::MsMs 20327 Specdb::MsMs 20328 Specdb::MsMs 20329 Specdb::MsMs 21668 Specdb::MsMs 21669 Specdb::MsMs 21670 Specdb::MsMs 21878 Specdb::MsMs 21879 Specdb::MsMs 21880 Specdb::MsMs 286452 Specdb::MsMs 286453 Specdb::MsMs 286454 Specdb::MsMs 286455 Specdb::MsMs 286456 Specdb::MsMs 373610 Specdb::MsMs 373611 Specdb::MsMs 373612 Specdb::MsMs 373613 Adipose Tissue 52170.21 nmol/g of tissue Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 57060.16 nmol/g of tissue Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 701466.83 nmol/g of tissue Perirenal (PF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 1011294.96 nmol/g of tissue Perirenal (PF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 676992.53 nmol/g of tissue Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue 856077.1 nmol/g of tissue Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed. C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20. Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue 965197.89 nmol/g of tissue Fatty acid of subcutaneous fat. Calf-finished Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 944139.03 nmol/g of tissue Fatty acid of subcutaneous fat. With growth promoting implants Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 975883.31 nmol/g of tissue Fatty acid of subcutaneous fat. Without growth promoting implants Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue 968356.72 nmol/g of tissue Fatty acid of subcutaneous fat. Yearling-finished Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41. 24188642 Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Adipose Tissue Cull beef cows fed barley silage diet for 12 weeks He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281. 22274861 Adipose Tissue Cull beef cows fed barley silage diet with flaxseed for 12 weeks He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281. 22274861 Adipose Tissue Cull beef cows fed hay for 12 weeks He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281. 22274861 Adipose Tissue Cull beef cows fed hay with flaxseed for 12 weeks He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281. 22274861 Adipose Tissue Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days. Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014. 25093808 Bladder 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 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 Fibroblasts 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 Kidney 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 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 29 +/- 1 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 104 +/- 4 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 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 54.3 +/- 2.2 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 47.3 +/- 2.3 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 16691.1 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 15989.14 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 3470.813 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 5303.71 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 3470.813 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 40167.831 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 38997.9 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 36658.02 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 90.04 +/- 12.70 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 106.07 +/- 14.43 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 50.79 +/- 2.60 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 13.85 +/- 2.31 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 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 78.82 +/- 1.33 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 45627.554 +/- 15209.185 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 124.325 +/- 0.62 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 220.8 +/- 41.8 uM Fat content of plain milk wasn't specified in the reference. 3.25% is an estimate. Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3. 11754544 Milk 131.1 +/- 22.8 uM Fat content of low-fat milk wasn't specified in the reference. 1-2% is an estimate. Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3. 11754544 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 48864.381 +/- 11699.373 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 49098.368 +/- 11270.396 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 396608.587 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 458615.239 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 479284.123 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Milk 491373.471 uM M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Muscle Samples have been collected from Heifer cows. Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub 2013 Jun 5. 23871026 Oocyte Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries. McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70. 10793638 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 Platelet 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 Prostate Tissue 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 Ruminal Fluid 243.0 +/- 35.0 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 243.1 +/- 35.1 uM Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Semen Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was authenticated by external standard reference(s). Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018. 29634739 Semen Identified in bull spermatozoa by GC-MS Menezes EB, Velho ALC, Santos F, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Uncovering sperm metabolome to discover biomarkers for bull fertility. BMC Genomics. 2019 Sep 18;20(1):714. doi: 10.1186/s12864-019-6074-6. 31533629 Skeletal Muscle 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 985 C00249 15756 960 FDB011679 DB03796 PALMITATE Palmitic_acid C00030479 34386 187 Xu, Yan; Ling, Li. A method for preparing conjugated linoleic acid and palmitic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 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 Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11. 9718493 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 Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. 5409465 Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. 19038946 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 M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en BMDBP00235 Hepatic triacylglycerol lipase Q3SZ79 LIPC Enzyme BMDBP00368 Fatty acid synthase Q71SP7 FASN Enzyme BMDBP01120 Long-chain-fatty-acid--CoA ligase ACSBG1 Q2KHW5 ACSBG1 Enzyme BMDBP01137 Acyl-protein thioesterase 1 Q3MHR0 LYPLA1 Enzyme BMDBP01138 Palmitoyl-protein thioesterase 1 P45478 PPT1 Enzyme BMDBP01341 Retinoid isomerohydrolase Q28175 RPE65 Enzyme BMDBP02926 Gastric triacylglycerol lipase Q29458 LIPF Enzyme