1.0 2016-09-30 22:28:08 UTC 2020-06-04 20:56:12 UTC BMDB0000305 BMDB00305 Vitamin A Vitamin a, also known as (13cis)-retinol, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Thus, vitamin a is considered to be an isoprenoid lipid molecule. Vitamin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Vitamin a exists in all living organisms, ranging from bacteria to humans. Vitamin a participates in a number of enzymatic reactions, within cattle. In particular, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme diacylglycerol O-acyltransferase 1. In addition, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme acyl-CoA wax alcohol acyltransferase 1. In cattle, vitamin a is involved in the metabolic pathway called the retinol metabolism pathway. Vitamin a is a potentially toxic compound. Vitamin a has been found to be associated with several diseases known as pregnancy, hemodialysis, and thyroid cancer; also vitamin a has been linked to the inborn metabolic disorders including abetalipoproteinemia. (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol (all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol all-trans Retinol all-trans-Retinyl alcohol all-trans-Vitamin a all-trans-Vitamin a alcohol Alphalin Aquasol a Chocola a Retinol Retinol (vit a) Retinolum trans-Retinol Vitamin a alcohol Vitamin a1 Vitamin a1 alcohol 11-cis-Retinol 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomer all trans Retinol all-trans-Retinol b-Retinol beta-Retinol Vitamin a C20H30O 286.4516 286.229665582 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol α-sol 68-26-8 C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+ FPIPGXGPPPQFEQ-OVSJKPMPSA-N belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Organic compounds Lipids and lipid-like molecules Prenol lipids Retinoids Retinoids Diterpenoids Fatty alcohols Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic homomonocyclic compound Diterpenoid Fatty acyl Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol Retinoid skeleton Aliphatic homomonocyclic compounds Fat-soluble vitamins Retinoids Retinoids retinol Solid melting_point 61 - 63 °C logp 5.68 BIOBYTE (1995) logp 6.38 ALOGPS logs -4.58 ALOGPS logp 4.69 ChemAxon pka_strongest_acidic 16.44 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol ChemAxon average_mass 286.4516 ChemAxon mono_mass 286.229665582 ChemAxon smiles C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C ChemAxon formula C20H30O ChemAxon inchi InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+ ChemAxon inchikey FPIPGXGPPPQFEQ-OVSJKPMPSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 97.92 ChemAxon polarizability 36.54 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Retinol Metabolism SMP0087260 Specdb::EiMs 432 Specdb::CMs 8618 Specdb::CMs 37414 Specdb::CMs 136707 Specdb::CMs 144441 Specdb::CMs 1057500 Specdb::NmrTwoD 1267 Specdb::MsMs 519 Specdb::MsMs 520 Specdb::MsMs 521 Specdb::MsMs 260733 Specdb::MsMs 260734 Specdb::MsMs 260735 Specdb::MsMs 280668 Specdb::MsMs 280669 Specdb::MsMs 280670 Specdb::MsMs 2473550 Specdb::MsMs 2473551 Specdb::MsMs 2473552 Specdb::MsMs 2489277 Specdb::MsMs 2489278 Specdb::MsMs 2489279 Specdb::NmrOneD 268188 Specdb::NmrOneD 268189 Specdb::NmrOneD 268190 Specdb::NmrOneD 268191 Specdb::NmrOneD 268192 Specdb::NmrOneD 268193 Specdb::NmrOneD 268194 Specdb::NmrOneD 268195 Specdb::NmrOneD 268196 Specdb::NmrOneD 268197 Specdb::NmrOneD 268198 Specdb::NmrOneD 268199 Specdb::NmrOneD 268200 Specdb::NmrOneD 268201 Specdb::NmrOneD 268202 Specdb::NmrOneD 268203 Specdb::NmrOneD 268204 Specdb::NmrOneD 268205 Specdb::NmrOneD 268206 Specdb::NmrOneD 268207 Adipose 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 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 Intestine 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 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 0.052 - 4.797 uM USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.653 - 2.308 uM Commercial milk Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74. 1333471 Milk 0.566 uM Raw milk. Diet: Low hay diet Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2. 16772583 Milk 126 IU/100 g Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013 Milk 0.0524 uM Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.470 +/- 0.0400 uM Spanish commercial milk; low-fat 1.5% International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526 Milk 1.120 +/- 0.280 uM Spanish commercial milk; low-fat 3.6% International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526 Milk 0.0800 +/- 0.0400 uM Spanish commercial milk; skim 0.3% fat International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526 Milk 0.0733 uM Milk, filled, fluid, with blend of hydrogenated vegetable oils USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.0733 uM Milk, filled, fluid, with lauric acid oil USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 4.797 uM Milk, fluid, nonfat, calcium fortified (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.126 uM Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.0527 uM Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.126 uM Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.241 uM Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.136 uM Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 1.99 uM Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.65 +/- 0.02 uM Quantified by LC-MS/MS in 1% milk 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 0.70 +/- 0.01 uM Quantified by LC-MS/MS in 2% milk 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 0.55 +/- 0.01 uM Quantified by LC-MS/MS in 3.25% milk 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 0.265 +/- 0.004 uM Quantified by LC-MS/MS in skim milk 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 0.586 - 58.596 uM Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 Milk 0.349 - 3.491 uM Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman & Hall, pp 347–402, 1997 Milk 1.3195 uM Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013 Milk 0.492 uM Milk, fluid, 1% fat, without added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 1.0997 uM Milk, low sodium, fluid USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.136 uM Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.157 uM Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.471 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 0.663 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 1.445 uM Milk, producer, fluid, 3.7% milkfat USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.136 uM Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.785 uM Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 1.0682 uM Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.105 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.147 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.105 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1.697 uM Milk, whole, 3.25% milkfat, with added vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 1.697 uM Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 1.0822 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 1.0613 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 1.187 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Neuron 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 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 Spleen 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 Testis 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 445354 C17276 17336 FDB023841 DB00162 CPD-13524 Vitamin_A C00031437 Isler, O.; Ronco, A.; Guex, W.; Hindley, N. C.; Huber, W.; Dialer, K.; Kofler, M. Esters and ethers of synthetic vitamin A. Helvetica Chimica Acta (1949), 32 489-505. Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74. 1333471 Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2. 16772583 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 Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. 28342601 International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526 Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman & Hall, pp 347–402, 1997 USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en BMDBP00601 Retinal dehydrogenase 1 P48644 ALDH1A1 Enzyme BMDBP00606 17-beta-hydroxysteroid dehydrogenase type 6 Q3T001 HSD17B6 Enzyme BMDBP00713 Retinol dehydrogenase 8 Q9N126 RDH8 Enzyme BMDBP00714 Lecithin retinol acyltransferase Q9BGL2 LRAT Enzyme BMDBP00715 Retinol dehydrogenase 5 Q27979 RDH5 Enzyme BMDBP00716 Retinol dehydrogenase 10 Q8HZT6 RDH10 Enzyme BMDBP01288 Retinol dehydrogenase 12 P59837 RDH12 Enzyme BMDBP01341 Retinoid isomerohydrolase Q28175 RPE65 Enzyme BMDBP01885 Cellular retinoic acid-binding protein 1 P62964 CRABP1 Enzyme BMDBP01888 Cellular retinoic acid-binding protein 2 Q5PXY7 CRABP2 Enzyme BMDBP01961 Beta-lactoglobulin P02754 LGB Enzyme BMDBP01962 Interstitial retinol binding protein Q28129 Enzyme BMDBP01963 Retinaldehyde-binding protein 1 P10123 RLBP1 Enzyme BMDBP01964 Retinol-binding protein 5 P82708 RBP5 Enzyme BMDBP01965 Retinol-binding protein 1 P02694 RBP1 Enzyme BMDBP01966 Retinol-binding protein 3 P12661 RBP3 Enzyme BMDBP01967 Receptor for retinol uptake STRA6 Q0V8E7 STRA6 Enzyme BMDBP01968 Retinol-binding protein 4 P18902 RBP4 Enzyme BMDBP01969 Retinol binding protein 1, cellular Q58DG0 RBP1 Enzyme BMDBP02834 Diacylglycerol O-acyltransferase 1 Q8MK44 DGAT1 Enzyme BMDBP02992 Patatin-like phospholipase domain-containing protein 2 Q2KI18 PNPLA2 Enzyme BMDBP02993 Cytochrome P450 26B1 E1BHJ4 CYP26B1 Enzyme BMDBP02994 Retinol saturase E1BDK9 RETSAT Enzyme