2.0 2012-05-31 13:54:52 -0600 2015-09-13 12:56:11 -0600 ECMDB01881 M2MDB000426 Propylene glycol Propylene glycol (1,2-propanediol) is an organic compound (a diol alcohol), usually a tasteless, odorless, and colorless clear oily liquid that is hygroscopic and miscible with water, acetone, and chloroform. It is manufactured by the hydration of propylene oxide. Propylene glycol is used as a solvent for intravenous, oral, and topical pharmaceutical preparations. It is generally considered safe. However in large doses it can be toxic, especially if given over a short period of time. (RS)-1,2-Propanediol (S)-propane-1,2-diol 1,2-(RS)-Propanediol 1,2-Dihydroxypropane 1,2-Propane-diol 1,2-Propanediol 1,2-Propylene glycol 1,2-Propylenglykol 2,3-Propanediol 2-Hydroxypropanol A-Propylene glycol Aliphatic alcohol Alpha-Propylene glycol Chilisa FE DL-1,2-Propanediol Dl-Propylene glycol Dowfrost Glycol Ilexan P Inhibited 1,2-propylene glycol Isopropylene glycol Methyl glycol Methylethyl glycol Methylethylene glycol Monopropylene glycol Prolugen Propane-1,2-diol Propanediol Propylene glycol Propylene glycol usp Propylenglycol Sentry Propylene Glycol Sirlene Solar Winter Ban Solargard P Trimethyl glycol Ucar 35 α-Propylene glycol C3H8O2 76.0944 76.0524295 propane-1,2-diol 1,2-propanediol 57-55-6 CC(O)CO InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3 DNIAPMSPPWPWGF-UHFFFAOYSA-N Liquid Cytosol Extra-organism Periplasm logp -1.10 ALOGPS logs 1.10 ALOGPS solubility 9.52e+02 g/l ALOGPS melting_point -60 oC logp -0.79 ChemAxon pka_strongest_acidic 14.47 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac propane-1,2-diol ChemAxon average_mass 76.0944 ChemAxon mono_mass 76.0524295 ChemAxon smiles CC(O)CO ChemAxon formula C3H8O2 ChemAxon inchi InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3 ChemAxon inchikey DNIAPMSPPWPWGF-UHFFFAOYSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 18.97 ChemAxon polarizability 8.01 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Pyruvate metabolism ec00620 Glycerolipid metabolism ec00561 fucose and rhamnose degradation In E. coli, L-fucose and L-rhamnose are metabolized through parallel pathways. The pathways converge after their corresponding aldolase reactions yielding the same products: lactaldehye. Via reactions catalyzed by proteins encoded in linked operons comprising a regulon, the methylpentose, alpha-L-rhamnopyranose and/or beta-L-rhamnopyranose, is taken into the cell through a proton symporter and metabolized, enabling E. coli to grow on it as a total source of carbon and energy. For alpha-L-rhamnopyranose, it is isomerized by a l-rhamnose mutarotase resulting in a beta-L-rhamnopyranose which is then isomerized into a keto-L-rhamnulose by a l-rhamnose isomerase. The keto-L-rhamnulose spontaneously changes into a L-rhamnulofuranose which is phosphorylated by a rhamnulokinase resulting in a L-rhamnulose 1-phosphate. This compound reacts with a rhamnulose-1-phosphate aldolase resulting in a dihydroxyacetone phosphate and a lactaldehyde. For beta-L-rhamnopyranose, it is isomerized by a L-fucose mutarotase resulting in a alpha-L-fucopyranose. This compound is then isomerized by an L-fucose isomerase resulting in a L-fuculose which in turn gets phosphorylated into an L-fuculose 1-phosphate through an L-fuculokinase. The compound L-fuculose 1-phosphate reacts with an L-fuculose phosphate aldolase through a dihydroxyacetone phosphate and a lactaldehyde. Two pathways can be used for degradation of L-lactaldehyde. Aerobically, it is converted via lactate to pyruvate, also an intermediate of glycolysis. Anaerobically, lactaldehyde reductase is induced which converts lactaldehyde into propane-1,2-diol. Under aerobic conditions, L-lactaldehyde is oxidized in two steps to pyruvate, thereby channeling all the carbons from fucose or rhamnose into central metabolic pathways. Under anaerobic conditions, L-lactaldehyde is reduced to L-1,2-propanediol, which is secreted into the environment. PW000826 Metabolic methylglyoxal degradation III In E. coli there are several pathways for the removal of methylglyoxal. In this pathway, methylglyoxal is reduced to acetol by the action of various enzymes possessing methylglyoxal reductase activity. Most of the enzymes that have been characterized with this activity belong to the NADPH-dependent aldo-keto reductase subfamily of the aldo-keto reductase (AKR) superfamily. AKRs are found in both prokaryotes and eukaryotes and catalyze the reduction of carbonyl-containing aldehyde and/or ketone containing compounds to their corresponding alcohols. A few dual-specificity AKRs are also able to utilize NADH. An AKR from E. coli has been identified that is NADH-specific (AKR11B2, the product of gene ydjG). AKRs have been of considerable interest in metabolic engineering studies. E. coli K-12 enzymes homologous to mammalian AKRs have been shown to catalyze the methylglyoxal reductase reaction. Overexpression of the aldo-keto reductase AKR14A1, encoded by the yghZ gene, leads to increased resistance to methylglyoxal. In addition, three other genes yeaE (yeaE), dkgA (yqhE), and dkgB (yafB) were shown to encode proteins with similar activities. All four proteins were purified, and shown to catalyze the reaction in vitro, in the presence of NADPH. Prolonged incubation of E. coli cell-free extracts with methylglyoxal resulted in conversion of acetol to (S)-propane-1,2-diol. The enzyme proposed to catalyze (S)-propane-1,2-diol production is L-1,2-propanediol dehydrogenase / glycerol dehydrogenase. In bacteria (S)-propane-1,2-diol is a dead-end metabolite and exits the cell rapidly. Although AKRs can reduce methylglyoxal to acetol, a methylglyoxal reductase (NADPH-dependent) encoded by an unknown gene was purified from E. coli and shown to convert methylglyoxal to lactaldehyde. (EcoCyc) PW002079 Metabolic methylglyoxal degradation III PWY-5453 L-lactaldehyde degradation (anaerobic) PWY0-1315 Specdb::CMs 787 Specdb::CMs 892 Specdb::CMs 2705 Specdb::CMs 27159 Specdb::CMs 29431 Specdb::CMs 30673 Specdb::CMs 31362 Specdb::CMs 38167 Specdb::EiMs 42 Specdb::NmrOneD 1777 Specdb::NmrOneD 2489 Specdb::NmrOneD 3184 Specdb::NmrOneD 5033 Specdb::NmrOneD 5034 Specdb::MsMs 1780 Specdb::MsMs 1781 Specdb::MsMs 1782 Specdb::MsMs 5546 Specdb::MsMs 5547 Specdb::MsMs 178701 Specdb::MsMs 178702 Specdb::MsMs 178703 Specdb::MsMs 181020 Specdb::MsMs 181021 Specdb::MsMs 181022 Specdb::NmrTwoD 1717 HMDB01881 1030 13835224 C00583 16196 PROPANE-1-2-DIOL 1,2-Propanediol 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. 21097882 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. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 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. 18331064 Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. 12097436 Brucks R, Nanavaty M, Jung D, Siegel F: The effect of ultrasound on the in vitro penetration of ibuprofen through human epidermis. Pharm Res. 1989 Aug;6(8):697-701. 2813262 Claverie F, Giordano-Labadie F, Bazex J: [Contact eczema induced by propylene glycol. Concentration and vehicle adapted for for patch tests] Ann Dermatol Venereol. 1997;124(4):315-7. 9739936 Li N, Liu Z, Jia X, Cui W, Wang W, Zhang X, Han C, Chen J, Wang M: [Study on the toxicological effect of chloropropanols on rats] Wei Sheng Yan Jiu. 2003 Jul;32(4):349-52. 14535099 Maltaris T, Dimmler A, Muller A, Binder H, Hoffmann I, Kohl J, Siebzehnrubl E, Beckmann MW, Dittrich R: The use of an open-freezing system with self-seeding for cryopreservation of mouse ovarian tissue. Reprod Domest Anim. 2005 Jun;40(3):250-4. 15943700 Li GL, van der Geest R, Chanet L, van Zanten E, Danhof M, Bouwstra JA: In vitro iontophoresis of R-apomorphine across human stratum corneum. Structure-transport relationship of penetration enhancement. J Control Release. 2002 Nov 7;84(1-2):49-57. 12399167 Fare JC, Guesnon P, Helouis JJ, Normand S, Andre JL, Duvaldestin P: [Intramuscular premedication with diazepam in a fat emulsion] Cah Anesthesiol. 1984 May-Jun;32(4):303-6. 6529665 Reichard GA Jr, Skutches CL, Hoeldtke RD, Owen OE: Acetone metabolism in humans during diabetic ketoacidosis. Diabetes. 1986 Jun;35(6):668-74. 3086164 Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. 3426740 Vaddi HK, Ho PC, Chan YW, Chan SY: Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum. Biol Pharm Bull. 2003 Feb;26(2):220-8. 12576684 Fernandez C, Marti-Mestres G, Ramos J, Maillols H: LC analysis of benzophenone-3: II application to determination of 'in vitro' and 'in vivo' skin penetration from solvents, coarse and submicron emulsions. J Pharm Biomed Anal. 2000 Dec;24(1):155-65. 11108549 Vaddi HK, Ho PC, Chan SY: Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry. J Pharm Sci. 2002 Jul;91(7):1639-51. 12115825 Gancevici GG: Role of complement inhibition in topical therapy of muco-cutaneous herpes simplex virus infections. Roum Arch Microbiol Immunol. 1993 Oct-Dec;52(4):293-303. 7827366 Liu JH, Gao D, He LQ, Moey LK, Hua K, Liu ZB: The phase diagram for the ternary system propylene glycol-sodium chloride-water and their application to platelet cryopreservation. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2003 Feb;11(1):92-5. 12667299 Rajasenan RS, Riley RJ, Leeder JS: Expression and inducibility of antigens in severe combined immunodeficient mice recognized by human anti-P450 antibodies. Toxicol Appl Pharmacol. 1995 Nov;135(1):89-99. 7482543 Decherchi P, Lammari-Barreault N, Cochard P, Carin M, Rega P, Pio J, Pellissier JF, Ladaique P, Novakovitch G, Gauthier P: CNS axonal regeneration with peripheral nerve grafts cryopreserved by vitrification: cytological and functional aspects. Cryobiology. 1997 May;34(3):214-39. 9160994 Trottet L, Owen H, Holme P, Heylings J, Collin IP, Breen AP, Siyad MN, Nandra RS, Davis AF: Are all aciclovir cream formulations bioequivalent? Int J Pharm. 2005 Nov 4;304(1-2):63-71. Epub 2005 Sep 1. 16139970 Miller DL, Wildnauer RH: Thermoanalytical probes for the analysis of physical properties of stratum corneum. J Invest Dermatol. 1977 Sep;69(3):287-9. 894064 Zar T, Graeber C, Perazella MA: Recognition, treatment, and prevention of propylene glycol toxicity. Semin Dial. 2007 May-Jun;20(3):217-9. 17555487 Tuck, Michael William Marshall. Preparation of propylene glycol by hydrogenation of glycerol. PCT Int. Appl. (2008), 20pp. http://hmdb.ca/system/metabolites/msds/000/001/472/original/HMDB01881.pdf?1358895490 Lactaldehyde reductase P0A9S1 FUCO_ECOLI fucO http://ecmdb.ca/proteins/P0A9S1.xml Glycerol dehydrogenase P0A9S5 GLDA_ECOLI gldA http://ecmdb.ca/proteins/P0A9S5.xml Propylene glycol + NAD <> Lactaldehyde + NADH + Hydrogen ion R02257 LACTALDREDUCT-RXN Propylene glycol + NAD <> acetol + NADH + Hydrogen ion RXN-8632 Hydrogen ion + NADH + Lactaldehyde <> NAD + Propylene glycol LACTALDREDUCT-RXN (S)-lactaldehyde + NADH + Hydrogen ion + Lactaldehyde > NAD + Propylene glycol PW_R002977 Hydroxyacetone + NADH + Hydrogen ion <> Propylene glycol + NAD PW_R006075