Biuret

Biuret
Identifiers
CAS number 108-19-0 Y
ChemSpider 7625 Y
KEGG C06555 Y
ChEBI CHEBI:18138 Y
Jmol-3D images Image 1
Properties
Molecular formula C2H5N3O2
Molar mass 103.08 g mol−1
Melting point

186–189 °C (decomposes)

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Biuret is a chemical compound with the chemical formula H2NC(O)NHC(O)NH2. It is the result of condensation of two molecules of urea and is a problematic impurity in urea-based fertilizers. This white solid is soluble in hot water.[1]

The term "biuret" also describes a family of organic compounds with the functional group -(HN-CO-)2N-. Thus dimethyl biuret is CH3HN-CO-NR'-CO-NHCH3. A variety of organic derivatives are possible.

Contents

Biuret test

The biuret test is a chemical test for proteins and polypeptides. It is based on the biuret reagent, a blue solution that turns violet upon contact with proteins, or any substance with peptide bonds. The test and reagent do not actually contain biuret; they are so named because both biuret and proteins have the same response to the test.

Preparation

The parent compound can be prepared by heating urea above the melting point at which temperature ammonia is expelled:[2]

2 CO(NH2)2 → H2N-CO-NH-CO-NH2 + NH3

In general, organic biurets are prepared by trimerization of isocyanates. For example the trimer of 1,6-hexamethylene diisocyanate is also known as HDI-biuret.

Applications

Biuret is also used as a non-protein nitrogen source in ruminant feed,[3] where it is converted into protein by gut microorganisms.[4] It is less favored than urea, due to its higher cost and lower digestibility[5] but this characteristic also slows down its digestion and so decreases the risk of ammonia toxicity.[5][6]

Related compounds

References

  1. ^ Biuret was first prepared and studied by Gustav Heinrich Wiedemann (1826 - 1899) for his doctoral dissertation, which was submitted in 1847. His findings were reported in several articles: (1) "Neues Zersetzungsproduct des Harnstoffs" (New decomposition product of urea) Journal für praktische Chemie, vol. 42, pages 255-256 (1847). [This notice reports that biuret reacts with alkaline copper sulfate to produce a red solution -- the so-called "Biuret test".]; (2) Gustav Wiedemann (1848) "Über eine neue, aus dem Harnstoff entstehende Verbindung" (On a new compound arising from urea) Journal für praktische Chemie, vol. 43, page 271-280; (3) G. Wiedemann (1848) "Biuret. Zersetzungsprodukt des Harnstoffs" (Biuret: decomposition product of urea), Liebig's Annalen der Chemie und Pharmacie, vol. 68, pages 323-326.
  2. ^ Jozef H. Meessen and Harro Petersen “Urea” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a27_333
  3. ^ Beef cattle feed, Encyclopædia Britannica Online
  4. ^ Florida Cow-Calf Management, 2nd Edition - Feeding the Cow Herd, IFAS Extension, University of Florida
  5. ^ a b Oltjen RR, Williams EE, Slyter LL, Richardson GV (November 1969). "Urea versus biuret in a roughage diet for steers". J. Anim. Sci. 29 (5): 816–22. PMID 5391979. http://jas.fass.org/cgi/pmidlookup?view=long&pmid=5391979. 
  6. ^ Paul V. Fonnesbeck, Leonard C. Kearl and Lorin E. Harris (1975). "Feed Grade Biuret as a Protein Replacement for Ruminants. A Review". J. Anim Sci. 40 (6): 1150–1184. http://jas.fass.org/cgi/content/abstract/40/6/1150.