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1

Prager, RH, and Z. Yurui. "Preparation of Carboxylate Esters of Polyhydric Alcohols by Using a Sulfonated Charcoal Catalyst." Australian Journal of Chemistry 42, no. 6 (1989): 1003. http://dx.doi.org/10.1071/ch9891003.

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2

O'Connor, Charmian J., and Richard H. Barton. "Quantitative 13C N.M.R. Assay and Assignment of Mixtures from Lipase Digestion of Propane-1,2-diol Dibutyrate." Australian Journal of Chemistry 52, no. 2 (1999): 123. http://dx.doi.org/10.1071/c98067.

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13C nuclear magnetic resonance (n.m.r.) spectra were obtained at 50 and 100 MHz for mixtures of propanediol, propane-1,2-diol dibutyrate, propane-1,2-diol 1-butyrate and propane-1,2-diol 2-butyrate in CDCl3. Distortionless enhancement by polarization transfer (DEPT) and two-dimensional 13C–1H correlation spectroscopy were used to confirm shift assignments. Spectra for the 1- and 2-monoesters showed strongly different inductive effects due to the position of the butyryl chain. These experiments demonstrate the desirability of using 13C n.m.r. rather than 1H n.m.r. spectroscopy in quantitative s
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3

Wesołowski, Wiktor, and MAŁGORZATA KUCHARSKA. "1,2-Propanediol Determination in working air with gas chromatography with mass spectrometer." Podstawy i Metody Oceny Środowiska Pracy 33, no. 2(92) (2017): 173–88. http://dx.doi.org/10.5604/01.3001.0010.0064.

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Propane-1,2-diol (propylene glycol, PG) is a color-less, strongly hygroscopic liquid used in the pro-duction of antifreeze fluids, polyester resins and detergents. The main use of propane-1,2-diol is in the cosmetic industry as an ingredient of creams, toothpastes, mouthwashes and deodorant sticks. It is also used in medicine, pharmaceutics, food and cleaning products. Propane-1,2-diol is used as a hygroscopic agent in the plastics industry, textile products and in manufacturing cigarettes. Recently, it is used as the main component of fluids used in electronic cigarettes. There are no reports
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4

O'Connor, Charmian J., and Richard H. Barton. "Acyl Transfer Isomerization of Glycerol 1,2-Dibutyrate and Propane-1,2-diol 1-Butyrate." Australian Journal of Chemistry 51, no. 6 (1998): 455. http://dx.doi.org/10.1071/c97212.

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The speciation of mixed butyrylglycerols (glycerol butyrates) and propanediol butyrate esters in the product mix from lamb pregastric lipase-catalysed hydrolysis of tributyrylglycerol and propane-1,2-diol dibutyrate has been examined by 13C n.m.r. spectroscopy. Samples from the quenched reaction mixture were extracted and allowed to stand in emulsion systems made up in bis tris propane buffer or water, pH 7·0, and in the absence of enzyme. There is clear evidence of uncatalysed conversion of rac-1,2-dibutyrylglycerol into the 1,3-isomer to form an equilibrium mixture containing c. 60–67% 1,3-i
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5

Wang, Yongli, Ming Li, Lijun Liu, Lina Zhou, and Jingkang Wang. "3-(2-Methoxyphenoxy)propane-1,2-diol." Acta Crystallographica Section E Structure Reports Online 61, no. 7 (2005): o1999—o2000. http://dx.doi.org/10.1107/s1600536805016909.

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6

Yang, Changsheng, Xue Feng, Yankai Sun, Qian Yang, and Juan Zhi. "Isobaric Vapor–Liquid Equilibrium for Two Binary Systems{Propane-1,2-diol + Ethane-1,2-diol and Propane-1,2-diol + Butane-1,2-diol} at p = (10.0, 20.0, and 40.0) kPa." Journal of Chemical & Engineering Data 60, no. 4 (2015): 1126–33. http://dx.doi.org/10.1021/je5010824.

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7

Gudelj, Martina, Paola Šurina, Lucija Jurko, Ante Prkić, and Perica Bošković. "The Additive Influence of Propane-1,2-Diol on SDS Micellar Structure and Properties." Molecules 26, no. 12 (2021): 3773. http://dx.doi.org/10.3390/molecules26123773.

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Micellar systems are colloids with significant properties for pharmaceutical and food applications. They can be used to formulate thermodynamically stable mixtures to solubilize hydrophobic food-related substances. Furthermore, micellar formation is a complex process in which a variety of intermolecular interactions determine the course of formation and most important are the hydrophobic and hydrophilic interactions between surfactant–solvent and solvent–solvent. Glycols are organic compounds that belong to the group of alcohols. Among them, propane-1,2-diol (PG) is a substance commonly used a
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8

Comerford, James W., Sam J. Hart, Michael North, and Adrian C. Whitwood. "Homogeneous and silica-supported zinc complexes for the synthesis of propylene carbonate from propane-1,2-diol and carbon dioxide." Catalysis Science & Technology 6, no. 13 (2016): 4824–31. http://dx.doi.org/10.1039/c6cy00134c.

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9

Villalba, Rafael, Joan Benitez, Enrique De No-Lowis, Luis F. Rioja, and J. Luis Gómez-Villagrán. "Cryopreservation of Human Skin with Propane-1,2-diol." Cryobiology 33, no. 5 (1996): 525–29. http://dx.doi.org/10.1006/cryo.1996.0056.

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10

Arnaud, F. G., and D. E. Pegg. "Cryopreservation of human platelets with propane-1,2-diol." Cryobiology 27, no. 2 (1990): 130–36. http://dx.doi.org/10.1016/0011-2240(90)90004-n.

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11

Jin, Changchun, Zhongyu Wang, Qisheng Huo, and Rulin Dong. "Different behaviors of PdAu/C catalysts in electrooxidation of propane-1,3-diol and propane-1,2-diol." Ionics 21, no. 3 (2014): 841–47. http://dx.doi.org/10.1007/s11581-014-1236-7.

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12

Woźnicka, Jadwiga, and Stefania Taniewska-Osińska. "Thermochemical investigation of NaI–glycerol–glycol (ethanediol, propane-1,2-diol, propane-1,3-diol) systems at 313.15 K." Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases 82, no. 5 (1986): 1299. http://dx.doi.org/10.1039/f19868201299.

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13

Cano-Gómez, José J., Gustavo A. Iglesias-Silva, Luis D. Cortez-Sánchez, and María T. Castillo-Escobedo. "Densities and Viscosities for Binary Liquid Mixtures of Butan-1-ol + Propane-1,2-diol, + Butane-1,2-diol and 2-Methylpropan-1-ol + Propane-1,2-diol, + Butane-1,2-diol from 298.15 to 333.15 K at 0.1 MPa." Journal of Chemical & Engineering Data 62, no. 12 (2017): 4252–65. http://dx.doi.org/10.1021/acs.jced.7b00621.

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14

Rich, S. J., and W. J. Armitage. "Corneal tolerance of vitrifiable concentrations of propane-1,2-diol." Cryobiology 28, no. 2 (1991): 159–70. http://dx.doi.org/10.1016/0011-2240(91)90018-j.

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15

Arnaud, F. G., C. J. Hunt, and D. E. Pegg. "Some effects of propane-1,2-diol on human platelets." Cryobiology 27, no. 2 (1990): 119–29. http://dx.doi.org/10.1016/0011-2240(90)90003-m.

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16

Pegg, D. E., I. A. Jacobsen, M. P. Diaper, and J. Foreman. "Perfusion of rabbit kidneys with solutions containing propane-1,2-diol." Cryobiology 24, no. 5 (1987): 420–28. http://dx.doi.org/10.1016/0011-2240(87)90045-9.

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17

Arnaud, F. G., and D. E. Pegg. "Permeation of glycerol and propane-1,2-diol into human platelets." Cryobiology 27, no. 2 (1990): 107–18. http://dx.doi.org/10.1016/0011-2240(90)90002-l.

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18

Mallidis, Con, David Phelan, Murray Coles, and Gayle Jones. "Does the composition of propane-1,2-diol alter over time?" Journal of Assisted Reproduction and Genetics 13, no. 1 (1996): 53–55. http://dx.doi.org/10.1007/bf02068870.

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19

Bakar, M. A., M. A. Islam ., S. Khatun ., and G. Sadik . "Subacute Toxicity Study of Malic Acid Propane 1,2-diol Copolyester." Journal of Medical Sciences 3, no. 4 (2003): 274–82. http://dx.doi.org/10.3923/jms.2003.274.282.

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20

Talismanov, V. S., S. V. Popkov, O. G. Karmanova, et al. "3-(IMIDAZOL-1-YL)PROPANE-1,2-DIOL AND 3-(1,2,4- TRIAZOL-1-YL)PROPANE-1,2-DIOL: SYNTHESIS AND THEIR TRANSFORMATION TO BIOACTIVE CYCLIC KETALS." Rasayan Journal of chemistry 14, no. 03 (2021): 1711–16. http://dx.doi.org/10.31788/rjc.2021.1436537.

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21

Mehrotra, Ram C., and Anirudh Singh. "ChemInform Abstract: Synthesis Structure and Properties of Mononuclear Oxovanadium(V) Alkoxides Incorporating Chelating Ethane-1,2-diol and Propane-1,2-diol." ChemInform 33, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.200222249.

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22

Uosaki, Yasuhiro, Sunao Kitaura, and Takashi Moriyoshi. "Static Relative Permittivities of Water + Propane-1,2-diol and Water + Propane-1,3-diol under Pressures up to 300 MPa at 298.15 K." Journal of Chemical & Engineering Data 50, no. 6 (2005): 2008–12. http://dx.doi.org/10.1021/je050237g.

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23

Casati, Silvana, Enzo Santaniello, and Pierangela Ciuffreda. "Enzymatic synthesis of both enantiomeric forms of 3-allyloxy-propane-1,2-diol." Tetrahedron: Asymmetry 23, no. 5 (2012): 395–400. http://dx.doi.org/10.1016/j.tetasy.2012.03.008.

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24

Kinart, Cezary M. "Study on the Internal Structures of Liquid Formamide-Propane-1,2-Diol Mixtures." Physics and Chemistry of Liquids 28, no. 1 (1994): 41–48. http://dx.doi.org/10.1080/00319109408029539.

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25

Shuklov, Ivan A., Natalia V. Dubrovina, Joachim Schulze, Wolfgang Tietz, and Armin Börner. "Synthesis of (R)-propane-1,2-diol from lactides by dynamic kinetic resolution." Tetrahedron Letters 55, no. 24 (2014): 3495–97. http://dx.doi.org/10.1016/j.tetlet.2014.04.097.

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26

Chupin, Vladimir, and Ivan Boldyrev. "3-{4-[(E)-{4-[(E)-Phenyldiazenyl]phenyl}diazenyl]phenoxy}propane-1,2-diol." Molbank 2017, no. 1 (2017): M932. http://dx.doi.org/10.3390/m932.

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27

Kimsanov, B. Kh, and M. B. Karimov. "Synthesis of ether-amines of propane-1,2-diol and their biological activity." Chemistry of Natural Compounds 33, no. 5 (1997): 501–5. http://dx.doi.org/10.1007/bf02254792.

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28

Rich, S. J., and W. J. Armitage. "Propane-1,2-diol and glycerol as components of vitrification solutions for corneas." Cryobiology 25, no. 6 (1988): 533–34. http://dx.doi.org/10.1016/0011-2240(88)90370-7.

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29

Záhonyi-Budó, Éva, and LászlóI Simándi. "Oxidation of propane-1,2-diol by acidic manganese(V) and manganese(VI)." Inorganica Chimica Acta 248, no. 1 (1996): 81–84. http://dx.doi.org/10.1016/0020-1693(95)04994-0.

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30

Anžlovar, Alojz, Zorica Crnjak Orel, and Majda Žigon. "Copper(I) oxide and metallic copper particles formed in 1,2-propane diol." Journal of the European Ceramic Society 27, no. 2-3 (2007): 987–91. http://dx.doi.org/10.1016/j.jeurceramsoc.2006.04.131.

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31

Speranza, Giovanna, Wolfgang Buckel, and Bernard T. Golding. "CoenzymeB12-dependent enzymatic dehydration of 1,2-diols: simple reaction, complex mechanism!" Journal of Porphyrins and Phthalocyanines 08, no. 03 (2004): 290–300. http://dx.doi.org/10.1142/s1088424604000271.

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The conversion of glycerol to acrolein is an undesirable event in whisky production, caused by infection of the broth with Klebsiella pneumoniae. This organism uses glycerol dehydratase to transform glycerol into 3-hydroxypropanal, which affords acrolein on distillation. The enzyme requires adenosylcobalamin (coenzyme B12) as cofactor and a monovalent cation (e.g. K+). Diol dehydratase is a similar enzyme that converts 1,2-diols ( C2- C4) including glycerol into an aldehyde and water. The subtle stereochemical features of these enzymes are exemplified by propane-1,2-diol: both enantiomers are
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32

Badertscher, René, Carola Freiburghaus, Daniel Wechsler, and Stefan Irmler. "Validated method for the determination of propane-1,2-diol, butane-2,3-diol, and propane-1,3-diol in cheese and bacterial cultures using phenylboronic esterification and GC–MS." Food Chemistry 230 (September 2017): 372–77. http://dx.doi.org/10.1016/j.foodchem.2017.03.069.

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33

Origlia-Luster, M. L., B. A. Patterson, and E. M. Woolley. "Apparent molar volumes and apparent molar heat capacities of aqueous ethane-1,2-diol, propane-1,2-diol, and propane-1,3-diol at temperatures from 278.15 K to 393.15 K and at the pressure 0.35 MPa." Journal of Chemical Thermodynamics 34, no. 4 (2002): 511–26. http://dx.doi.org/10.1006/jcht.2001.0883.

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34

Zakharychev, D. V., S. N. Lazarev, Z. A. Bredikhina, and A. A. Bredikhin. "Crystallization of chiral compounds 3. 3-phenoxypropane-1,2-diol and 3-(2-halophenoxy)propane-1,2-diols." Russian Chemical Bulletin 55, no. 2 (2006): 230–37. http://dx.doi.org/10.1007/s11172-006-0243-x.

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35

Lajšic, Stevan, Gordana Cetkovic, Mirjana Popsavin, Velimir Popsavin, and Dušan Miljković. "Fischer Indole Synthesis with Selected 2,3-Dideoxy-D-glycero-aldopentose Derivatives. Conversion of D-Xylose to (2S)-3-(Indol-3-yl)propane-1,2-diol." Collection of Czechoslovak Chemical Communications 61, no. 2 (1996): 298–304. http://dx.doi.org/10.1135/cccc19960298.

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Two independent routes towards (2S)-3-(indol-3-yl)propane-1,2-diol (11) were achieved starting from 3,5-di-O-acetyl-1,2-O-cyclohexylidene-α-D-xylofuranose (1). Ethanethiolysis of 1 afforded acyclic diethyl dithioacetal 2 which was further O-deacetylated to give 3. Selective benzoylation of 3 gave 5-O-benzoyl derivative 4. Treatment of 4 with N-bromosuccinimide in methanol gave methyl furanoside 5 which was further desulfurized over Raney nickel to afford 6. An acid hydrolysis of 6 gave hemiacetal 7 which upon treatment with phenylhydrazine, according to standard Fischer indolization procedure,
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36

Cooper, T. G., J. P. Barfield, and C. H. Yeung. "The tonicity of murine epididymal spermatozoa and their permeability towards common cryoprotectants and epididymal osmolytes." REPRODUCTION 135, no. 5 (2008): 625–33. http://dx.doi.org/10.1530/rep-07-0573.

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The permeability of murine cauda epididymidal spermatozoa was determined from the swelling caused by penetrating agents at isotonicity, which lies between 422 and 530 mmol/kg. Spermatozoa were permeable to a range of solutes with size <200 Da. Relative entry rates of cryoprotective agents (CPAs) were ethylene glycol≈DMSO>propane-1,2-diol>glycerol>propane-1,3-diol. More polar compounds including major epididymal secretions were impermeant. None of the compounds entered spermatozoa through quinine-sensitive channels; rather, quinine increased the size of solute-swollen spermatozoa, s
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37

Mochizuki, Naoki, and Katsuaki Kitabatake. "Analysis of 1-(2-furyl)propane-1,2-diol, a furfural metabolite in beer." Journal of Fermentation and Bioengineering 83, no. 4 (1997): 401–3. http://dx.doi.org/10.1016/s0922-338x(97)80152-3.

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38

Wusteman, Monica C., David E. Pegg, Li-Hong Wang, and Martin P. Robinson. "Vitrification of ECV304 cell suspensions using solutions containing propane-1,2-diol and trehalose." Cryobiology 46, no. 2 (2003): 135–45. http://dx.doi.org/10.1016/s0011-2240(03)00019-1.

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39

Fayzullin, R. R., Z. A. Bredikhina, D. R. Sharafutdinova, O. B. Bazanova, and A. A. Bredikhin. "Chiral lariat ethers based on spontaneously resolved 3-(2-cyanophenoxy)propane-1,2-diol." Russian Journal of Organic Chemistry 50, no. 4 (2014): 611–13. http://dx.doi.org/10.1134/s1070428014040319.

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40

Saini, Mohini, J. P. Nagpaul, and M. K. P. Amma. "Effect of propane-1,2-diol ingestion on carbohydrate metabolism in female rat erythrocytes." Journal of Applied Toxicology 13, no. 1 (1993): 69–75. http://dx.doi.org/10.1002/jat.2550130114.

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41

Rich, S. J., and W. J. Armitage. "Propane-1,2-diol as a potential component of a vitrification solution for corneas." Cryobiology 27, no. 1 (1990): 42–54. http://dx.doi.org/10.1016/0011-2240(90)90051-5.

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42

Zhong, Kai-Long. "Bis(1,10-phenanthroline-κ2N,N′)(sulfato-κO)zinc(II) propane-1,2-diol monosolvate". Acta Crystallographica Section E Structure Reports Online 69, № 10 (2013): m561. http://dx.doi.org/10.1107/s160053681302610x.

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43

Rajak, Kajal Krishna, Sujit Mondal, and Sankar Prasad Rath. "Synthesis, structure and properties of mononuclear oxovanadium(V) alkoxides incorporating chelated ethane-1,2-diol and propane-1,3-diol." Polyhedron 19, no. 8 (2000): 931–36. http://dx.doi.org/10.1016/s0277-5387(00)00336-3.

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44

Soni, Zinal, Santosh Patil, Santhosh Koppula, and Poonam Koppula. "Ultrasound-assisted efficient synthesis of 3-[4-(2-methoxyethyl) phenoxy] propane -1,2 -diol (Metoprolol EP impurity D)." Organic Communications 14, no. 1 (2021): 92–96. http://dx.doi.org/10.25135/acg.oc.98.20.10.1844.

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Safety of the drug molecule is dependent on the various impurities formed during chemical transformation which may cause drug product instability, decreased product performance, loss in potency, and/or formation of potentially genotoxic impurities. Therefore, it is essential to identify and quantify the impurities generated during the drug development stage. Herein, we describe the synthesis and characterization of Impurity D of Metoprolol, 3-[4-(2-methoxyethyl)phenoxy]propane-1,2-diol (1), reported in European Pharmacopeia. The synthesis of impurity D has been accomplished in two steps; start
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45

Djurendic, Evgenija, Marina Savic, Suzana Jovanovic-Santa, et al. "Antioxidant and cytotoxic activity of mono- and bissalicylic acid derivatives." Acta Periodica Technologica, no. 45 (2014): 173–89. http://dx.doi.org/10.2298/apt1445173d.

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A simple synthesis of mono- and bis-salicylic acid derivatives 1-10 by the transesterification of methyl salicylate (methyl 2-hydroxybenzoate) with 3-oxapentane-1,5-diol, 3,6- dioxaoctane-1,8-diol, 3,6,9-trioxaundecane-1,11-diol, propane-1,2-diol or 1-aminopropan- 2-ol in alkaline conditions is reported. All compounds were tested in vitro on three malignant cell lines (MCF-7, MDA-MB-231, PC-3) and one non-tumor cell line (MRC- 5). Strong cytotoxicity against prostate PC-3 cancer cells expressed compounds 3, 4, 6, 9 and 10, all with the IC50 less than 10 ?mol/L, which were 11-27 times higher th
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46

Paynter, Sharon J., Louise O’Neil, Barry J. Fuller, and Robert W. Shaw. "Membrane permeability of human oocytes in the presence of the cryoprotectant propane-1,2-diol." Fertility and Sterility 75, no. 3 (2001): 532–38. http://dx.doi.org/10.1016/s0015-0282(00)01757-x.

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47

Yasir, Ahmed, Kartikeya Shukla, and Vimal Chandra Srivastava. "Synthesis of Propylene Carbonate from Propane-1,2-diol and Urea Using Hydrotalcite-Derived Catalysts." Energy & Fuels 31, no. 9 (2017): 9890–97. http://dx.doi.org/10.1021/acs.energyfuels.7b01330.

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48

Aktaş, Derya, Meryem Fıstıkçı, Özlem Gündoğdu, et al. "Novel and Stereospecific Synthesis of (2S)-3-(2,4,5-Trifluorophenyl)propane-1,2-diol fromD-Mannitol." Helvetica Chimica Acta 98, no. 8 (2015): 1127–31. http://dx.doi.org/10.1002/hlca.201500031.

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49

KIMSANOV, B. K., and M. B. KARIMOV. "ChemInform Abstract: Synthesis of Ether-amines of Propane-1,2-diol and Their Biological Activity." ChemInform 29, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199848328.

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50

Rietz, Roland, Gerald Brezesinski, and Helmuth Möhwald. "Separation of Enantiomers in a Monolayer of Racemic 3-Hexadecyl-oxy-propane-1,2-diol." Berichte der Bunsengesellschaft für physikalische Chemie 97, no. 10 (1993): 1394–98. http://dx.doi.org/10.1002/bbpc.19930971036.

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