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1-Hydroxyethylidene-1,1-diphosphonic acid

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1-Hydroxyethylidene-1,1-diphosphonic acid Basic information
1-Hydroxyethylidene-1,1-diphosphonic acid Chemical Properties
  • Melting point:198~199℃
  • Boiling point:578.8±60.0 °C(Predicted)
  • Density 1.45 (60% aq.)
  • pka1.35, 2.87, 7.03, 11.3(at 25℃)
  • form Powder
  • color white
  • PHpH (1.7→100, 25℃) : 1.3~1.8
  • Water Solubility Soluble in water.
  • Merck 14,3863
  • BRN 1789291
  • Stability:Stable. Incompatible with strong oxidizing agents.
  • CAS DataBase Reference2809-21-4(CAS DataBase Reference)
  • EPA Substance Registry SystemEtidronic acid (2809-21-4)
Safety Information
1-Hydroxyethylidene-1,1-diphosphonic acid Usage And Synthesis
  • Chemical Propertieslight beige powder
  • OriginatorEtidron,Gentili,Italy,1977
  • UsesEtidronate (Didronel) is a human protein tyrosine phosphatase inhibitor with IC50 of 0.2 μM.
  • DefinitionChEBI: A 1,1-bis(phosphonic acid) that is (ethane-1,1-diyl)bis(phosphonic acid) having a hydroxy substituent at the 1-position. It inhibits the formation, growth, and dissolution of hydroxyapatite crystals by chemisorption to calcium phosphate surfaces.
  • Manufacturing ProcessPhosphorous acid was premixed with acetic acid to form a 50 wt % solution of phosphorous acid dissolved in acetic acid. The acids were mixed on a molar basis of 1.36:1, acetic acid to phosphorous acid, and this corresponded on a mol percentage basis to 57.6% acetic acid and 42.4% phosphorous acid. Acetic anhydride was continuously metered into a stream of the phosphorous acid-acetic acid mixture to form the reaction solution. The acetic anhydride was metered into the acid mixture at a mol ratio of 1.33 mols of acetic anhydride per mol of phosphorous acid. The metering rates were 18.5 lb/hr of the phosphorous acid/acetic acid premixed solution and 15.1 lb/hr acetic anhydride. The reaction solution was continuously passed through a heat exchanger where it was heated to 190°F then it was continuously fed into a two stage back-mix reaction zone where due to the heat of reaction the temperature rose to 275°F. The average residence in the reaction zone was 27 min. The reaction zone consisted of two back-mix reactors each having a capacity of 7.5 pounds of the reaction solution. A stream of reaction solution was continuously with drawn from the second reactor and continuously mixed with a stream of water which was being metered at a rate of 2 lb/hr. This amount of water corresponded to 18% excess over the theoretical amount necessary to hydrolyze all of the acetyl-containing compounds in the reaction solution to free acids. The hydrolyzed solution was continuously passed through a heat exchanger and cooled to room temperature after which the solution was continuously passed to a crystallizer where, with agitation, the ethane-1-hydroxy-1,1-diphosphonic acid crystallized. The slurry was then filtered and the crystals were recovered and dried. Analysis of the product showed a conversion rate of phosphorous acid to ethane-1-hydroxy-1,1- diphosphonic acid of 86%. Sodium hydroxide may be used to give the disodium salt.
  • brand nameDidronel (Millot Laboratories, France); Didronel (Procter & Gamble).
  • Therapeutic FunctionBone calcium regulator
1-Hydroxyethylidene-1,1-diphosphonic acid Preparation Products And Raw materials
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