3-Hydroxypropionic acid can be obtained by base-induced hydration of acrylic acid followed by reacidification. Another synthesis involves cyanation of ethylene chlorohydrin followed by hydrolysis of the resulting nitrile. Hydrolysis of propiolactone is yet another route.[3] Propiolactone, the dehydrated derivative of 3-hydroxypropionic acid, is produced by reaction of ketene and formaldehyde.[4]
3-Hydroxypropionic acid is listed as one of the "top" chemicals that could be produced from renewable resources. In particular, it could be produced by manipulation of glycerol, but this technology has not reached a commercial stage.[5] It can also be produced from glucose via pyruvate and malonyl coenzyme A.[4][6]
Potential applicationsedit
3-Hydroxypropionic acid is of interest as a bio-derived precursor to acrylic acid.[5]
The polyester poly(3-hydroxypropionic acid) is a biodegradable polymer.[7] The method combines the high-molecular weight and control aspects of ring-opening polymerization with the commercial availability of the beta hydroxy acid, 3-hydroxypropionic acid which is abbreviated as 3-HP. Since 3-HPA can be derived from biological sources, the resulting material, poly(3-hydroxypropionic acid) or P(3-HPA), is biorenewable.
3-Hydroxypropionic acid can be produced by engineered microbes.[8]
A genetically encoded 3-hydroxypropionic acid inducible system has been characterized in bacteria demonstrating that such system in combination with fluorescent reporter protein can be utilized as a biosensor to measure intracellular and extracellular 3-HP concentrations by fluorescence output.[9]
^ abMika, László T.; Cséfalvay, Edit; Németh, Áron (2018). "Catalytic Conversion of Carbohydrates to Initial Platform Chemicals: Chemistry and Sustainability". Chemical Reviews. 118 (2): 505–613. doi:10.1021/acs.chemrev.7b00395. PMID 29155579.
^ abBozell, Joseph J.; Petersen, Gene R. (2010). "Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy's "Top 10" revisited". Green Chemistry. 12 (4): 539. doi:10.1039/b922014c.
^"Scientists Engineer Extreme Microorganisms to Make Fuel from Atmospheric Carbon Dioxide". 27 March 2013.
^Hanko, E.K.R.; Minton, N.P.; Malys, N. (2017). "Characterisation of a 3-hydroxypropionic acid-inducible system from Pseudomonas putida for orthogonal gene expression control in Escherichia coli and Cupriavidus necator". Scientific Reports. 7 (1724): 1724. Bibcode:2017NatSR...7.1724H. doi:10.1038/s41598-017-01850-w. PMC5431877. PMID 28496205.
hydroxypropionic, acid, carboxylic, acid, specifically, beta, hydroxy, acid, acidic, viscous, liquid, with, very, soluble, water, soluble, ethanol, diethyl, ether, upon, distillation, dehydrates, form, acrylic, acid, occasionally, called, hydracrylic, acid, na. 3 Hydroxypropionic acid is a carboxylic acid specifically a beta hydroxy acid It is an acidic viscous liquid with a pKa of 4 9 2 It is very soluble in water soluble in ethanol and diethyl ether Upon distillation it dehydrates to form acrylic acid and is occasionally called hydracrylic acid3 Hydroxypropionic acid 1 Names Preferred IUPAC name 3 Hydroxypropanoic acid Other names 3 Hydroxypropionic acidHydracrylic acidEthylene lactic acid Identifiers CAS Number 503 66 2 Y 3D model JSmol Interactive image 3DMet B00221 Beilstein Reference 773806 ChEBI CHEBI 33404 Y ChEMBL ChEMBL1205969 ChemSpider 61460 Y DrugBank DB03688 Y ECHA InfoCard 100 007 250 EC Number 207 974 8 KEGG C01013 Y PubChem CID 68152 UNII C4ZF6XLD2X CompTox Dashboard EPA DTXSID50198305 InChI InChI 1S C3H6O3 c4 2 1 3 5 6 h4H 1 2H2 H 5 6 YKey ALRHLSYJTWAHJZ UHFFFAOYSA N YInChI 1 C3H6O3 c4 2 1 3 5 6 h4H 1 2H2 H 5 6 Key ALRHLSYJTWAHJZ UHFFFAOYAU SMILES O C O CCO Properties Chemical formula C3H6O3 Molar mass 90 08 g mol Melting point lt 25 C143 C sodium salt Boiling point Decomposes Solubility in water Very soluble Acidity pKa 4 87 2 Related compounds Related carboxylic acids acetic acidglycolic acidpropionic acidlactic acidmalonic acidbutyric acidhydroxybutyric acid Related compounds 1 propanol2 propanolpropionaldehydeacrolein Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references 3 Hydroxypropionic acid is used in the industrial production of various chemicals such as acrylates Contents 1 Synthesis 2 Potential applications 3 Genetically encoded 3 hydroxypropionic acid inducible system 4 See also 5 References 6 External linksSynthesis edit3 Hydroxypropionic acid can be obtained by base induced hydration of acrylic acid followed by reacidification Another synthesis involves cyanation of ethylene chlorohydrin followed by hydrolysis of the resulting nitrile Hydrolysis of propiolactone is yet another route 3 Propiolactone the dehydrated derivative of 3 hydroxypropionic acid is produced by reaction of ketene and formaldehyde 4 3 Hydroxypropionic acid is listed as one of the top chemicals that could be produced from renewable resources In particular it could be produced by manipulation of glycerol but this technology has not reached a commercial stage 5 It can also be produced from glucose via pyruvate and malonyl coenzyme A 4 6 Potential applications edit3 Hydroxypropionic acid is of interest as a bio derived precursor to acrylic acid 5 The polyester poly 3 hydroxypropionic acid is a biodegradable polymer 7 The method combines the high molecular weight and control aspects of ring opening polymerization with the commercial availability of the beta hydroxy acid 3 hydroxypropionic acid which is abbreviated as 3 HP Since 3 HPA can be derived from biological sources the resulting material poly 3 hydroxypropionic acid or P 3 HPA is biorenewable Genetically encoded 3 hydroxypropionic acid inducible system edit3 Hydroxypropionic acid can be produced by engineered microbes 8 A genetically encoded 3 hydroxypropionic acid inducible system has been characterized in bacteria demonstrating that such system in combination with fluorescent reporter protein can be utilized as a biosensor to measure intracellular and extracellular 3 HP concentrations by fluorescence output 9 See also editLactic acid 2 hydroxypropanoic acid listed as hydracrylic acid in the Merck index 12th EditionReferences edit Merck Index 11th Edition 4681 a b Handbook of Chemistry and Physics CRC press 58th edition page D150 151 1977 Miltenberger Karlheinz 2000 Hydroxycarboxylic Acids Aliphatic Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a13 507 ISBN 978 3527306732 a b Mika Laszlo T Csefalvay Edit Nemeth Aron 2018 Catalytic Conversion of Carbohydrates to Initial Platform Chemicals Chemistry and Sustainability Chemical Reviews 118 2 505 613 doi 10 1021 acs chemrev 7b00395 PMID 29155579 a b Bozell Joseph J Petersen Gene R 2010 Technology development for the production of biobased products from biorefinery carbohydrates the US Department of Energy s Top 10 revisited Green Chemistry 12 4 539 doi 10 1039 b922014c Liu Changshui Ding Yamei Xian Mo Liu Min Liu Huizhou Ma Qingjun Zhao Guang 2017 Malonyl CoA pathway A promising route for 3 hydroxypropionate biosynthesis Critical Reviews in Biotechnology 37 7 933 941 doi 10 1080 07388551 2016 1272093 PMID 28078904 3 HP Retrieved 27 May 2011 Scientists Engineer Extreme Microorganisms to Make Fuel from Atmospheric Carbon Dioxide 27 March 2013 Hanko E K R Minton N P Malys N 2017 Characterisation of a 3 hydroxypropionic acid inducible system from Pseudomonas putida for orthogonal gene expression control in Escherichia coli and Cupriavidus necator Scientific Reports 7 1724 1724 Bibcode 2017NatSR 7 1724H doi 10 1038 s41598 017 01850 w PMC 5431877 PMID 28496205 External links editChisholm Hugh ed 1911 Hydracrylic Acid Encyclopaedia Britannica Vol 14 11th ed Cambridge University Press p 34 Retrieved from https en wikipedia org w index php title 3 Hydroxypropionic acid amp oldid 1221720147, wikipedia, wiki, book, books, library,
