138-08-9

Basic information

• Product Name: 2-dihydroxyphosphinoyloxyacrylic acid
• Synonyms: 2-dihydroxyphosphinoyloxyacrylic acid;Phosphoenolpyruvicacid;2-phosphonooxyprop-2-enoic acid;phosphopyruvic acid;2-(Dihydroxyphosphinyloxy)acrylic acid;2-(Phosphonooxy)acrylic acid;2-Phosphoenolpyruvate;2-Phosphonooxypropenoic acid
• CAS NO: 138-08-9
• Molecular Formula: C₃H₅O₆P
• Molecular Weight: 168.041961
• EINECS: 205-312-2
• Mol File: 138-08-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 466.7 °C at 760 mmHg
• Flash Point: 236.1 °C
• Appearance: /
• Density: 1.804 g/cm³
• Vapor Pressure: 5.29E-10mmHg at 25°C
• Refractive Index: 1.53
• PKA: 1.39±0.10(Predicted)
• CAS DataBase Reference: 2-dihydroxyphosphinoyloxyacrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-dihydroxyphosphinoyloxyacrylic acid(138-08-9)
• EPA Substance Registry System: 2-dihydroxyphosphinoyloxyacrylic acid(138-08-9)

Safety Data

• Hazardous Substances Data: 138-08-9(Hazardous Substances Data)

Usage

General Description

2-dihydroxyphosphinoyloxyacrylic acid is a compound with the chemical formula C4H7O8P. It is a phosphorus-containing organic acid and is also known as DHPOA. 2-dihydroxyphosphinoyloxyacrylic acid is often used in the synthesis of various organic molecules and is of interest in the field of medicinal chemistry due to its potential pharmaceutical applications. It is a multifunctional molecule, containing both hydroxyl and phosphinoyloxy groups, which makes it versatile for various chemical reactions and transformations. The presence of a phosphorus atom in the molecule also gives it unique properties and reactivity, making it useful in the development of new drugs and materials.

InChI:InChI=1/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)

Upstream product

• 1713-85-5 3-chloro-2-hydroxypropanoic acid 
• 3443-57-0 D-(+)-2-phosphoglyceric acid 
• 820-11-1 D-(-)-3-phosphoglyceric acid 
• 408511-01-3 2-phosphonooxy-acrylic acid methyl ester 
• 127-17-3 2-oxo-propionic acid 
• 807306-71-4 3,7-bis(dimethylamine)phenothiazonium 
• 110-17-8 (2E)-but-2-enedioic acid 
• 23998-95-0 Monobenzylphosphoenolbrenztraubensaeure 
• 91130-20-0 P-Methyl-P-phenyl-phosphoenol-brenztraubensaeure-ester 
• 92425-25-7 P_.P-Diphenyl-phosphoenol-brenztraubensaeure-ester 
• 4185-81-3 2-hydroxyacrylic acid dimethyl phosphate 
• 5824-58-8 3‐phosphopyruvate 
• 91-22-5 quinoline 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 328-42-7 Oxalacetic acid 
• 86-01-1 Guanosine 5'-triphosphate 
• 67-07-2 Phosphocreatine 
• 56-73-5 D-glucose 6-phosphate 
• 57-60-3 piruvate 
• 89771-75-5 5-enol-pyruvoylshikimate 3-phosphate (EPSP) 
• 59013-75-1 L-α-methylmethionine 
• 4265-07-0 phospho(enol)pyruvic acid mono potassium salt 
• 5824-58-8 3‐phosphopyruvate 
• 127-17-3 2-oxo-propionic acid 
• 63-39-8 UTP 
• 70222-94-5 UDP-N-acetylglucosamine-enolpyruvate 
• 17730-98-2 diadenosine tetraphosphate 
• 86119-84-8 phosphoric acid 

Relevant articles and documents

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Thermodynamics of the hydrolysis reactions of adenosine 3′,5′-(cyclic)phosphate(aq) and phosphoenolpyruvate(aq); the standard molar formation properties of 3′,5′-(cyclic)phosphate(aq) and phosphoenolpyruvate(aq)

Molar calorimetric enthalpy changes ΔrHm(cal) have been measured for the biochemical reactions {cAMP(aq) + H2O(l) = AMP(aq)} and {PEP(aq) + H2O(l) = pyruvate(aq) + phosphate(aq)}. The reactions were catalyzed, respectively, by phosphodiesterase 3prime;,5prime;-cyclic nucleotide and by alkaline phosphatase. The results were analyzed by using a chemical equilibrium model to obtain values of standard molar enthalpies of reaction ΔrHmo for the respective reference reactions {cAMp-(aq) + H2O(l) = HAMP-(aq)} and {PEP3-(aq) + H2O(l) = pyruvate-(aq) + HPO42-(aq)}. Literature values of the apparent equilibrium constants K′ for the reactions {ATP(aq) = cAMP(aq) + pyrophosphate(aq)K {ATP(aq) + pyruvate(aq) = ADP(aq) + PEP(aq)}, and {ATP(aq) + pyruvate(aq) + phosphate(aq) = AMP(aq) + PEP(aq) + pyrophosphate(aq)} were also analyzed by using the chemical equilibrium model. These calculations yielded values of the equilibrium constants K and standard molar Gibbs free energy changes ΔrGmo for ionic reference reactions that correspond to the overall biochemical reactions. Combination of the standard molar reaction property values (K, ΔrH mo, and ΔrGmo) with the standard molar formation properties of the AMP, ADP, ATP, pyrophosphate, and pyruvate species led to values of the standard molar enthalpy ΔfHmo, and Gibbs free energy of formation ΔfGmo and the standard partial molar entropy Smo of the cAMP and PEP species. The thermochemical network appears to be reasonably well reinforced and thus lends some confidence to the accuracy of the calculated property values of the variety of species involved in the several reactions considered herein. Published by Elsevier Ltd.

Pyruvate ester composition and method of use for resuscitation after events of ischemia and reperfusion

A therapeutic composition comprising an alkyl, aralkyl, alkoxyalkyl or carboxyalkyl ester of 2-ketoalkanoic acid and a component for inducing and stabilizing the enol resonance form of the ester at physiological pH values is disclosed. The composition of the invention further comprises a pharmceutically acceptable carier vehicle in which the enol resonance form of the ester is stabilized at physiological pH values. Formulations containing the compositions of the invention permit the successful use of 2-ketoalkanoic acid esters, e.g., pyruvic acid esters, to treat, e.g., ischemic events, shock, organ reanimation, resuscitation and other recognized pyruvate-effective treatments. The compositions of the inventions are also useful in a process for preserving organ parts, organs or limbs removed from a living mammal and in need of preservation, e.g., for later transplantation to an organ recipient.