Tris

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Tris
Chemical structure of tris
Identifiers
CAS number77-86-1 YesY
PubChem6503
ChemSpider6257 YesY
UNII023C2WHX2V YesY
KEGGD00396 YesY
ChEBICHEBI:9754 YesY
ChEMBLCHEMBL1200391 N
RTECS numberTY2900000
ATC codeB05BB03,B05XX02
Jmol-3D imagesImage 1
Properties
Molecular formulaC4H11NO3
Molar mass121.14 g mol−1
AppearanceWhite crystalline powder
Density1.328g/cm3
Melting point>175-176 °C (448-449 K)
Boiling point219 °C (426 °F; 492 K)
Solubility in water~50 g/100 mL (25 °C)
Acidity (pKa)8.07
Hazards
MSDSExternal MSDS
R-phrasesR36 R37 R38
S-phrasesS26 S36
Main hazardsIrritant
NFPA 704
Flash pointNon-flammable
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
 
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This article is about the chemical widely used as a biochemical buffer. For other uses, see Tris (disambiguation).
Tris
Chemical structure of tris
Identifiers
CAS number77-86-1 YesY
PubChem6503
ChemSpider6257 YesY
UNII023C2WHX2V YesY
KEGGD00396 YesY
ChEBICHEBI:9754 YesY
ChEMBLCHEMBL1200391 N
RTECS numberTY2900000
ATC codeB05BB03,B05XX02
Jmol-3D imagesImage 1
Properties
Molecular formulaC4H11NO3
Molar mass121.14 g mol−1
AppearanceWhite crystalline powder
Density1.328g/cm3
Melting point>175-176 °C (448-449 K)
Boiling point219 °C (426 °F; 492 K)
Solubility in water~50 g/100 mL (25 °C)
Acidity (pKa)8.07
Hazards
MSDSExternal MSDS
R-phrasesR36 R37 R38
S-phrasesS26 S36
Main hazardsIrritant
NFPA 704
Flash pointNon-flammable
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Tris, also known as THAM (the shorter names being abbreviations of tris(hydroxymethyl)aminomethane), is an organic compound with the formula (HOCH2)3CNH2. Tris is extensively used in biochemistry and molecular biology.[1] In biochemistry, Tris is widely used as a component of buffer solutions, such as in TAE and TBE buffer, especially for solutions of nucleic acids. It contains a primary amine and thus undergoes the reactions associated with typical amines, e.g. condensations with aldehydes.

Buffering features[edit]

Tris has a pKa of 8.07 at 25 °C, which implies that the buffer has an effective pH range between 7.07 and 9.07.

Buffer details[edit]

Buffer inhibition[edit]

Preparation[edit]

Tris is prepared industrially in two steps from nitromethane via the intermediate (HOCH2)3CNO2. Reduction of the latter gives tris(hydroxymethyl)aminomethane.[6]

Uses[edit]

The useful buffer range for tris (7-9) coincides with the physiological pH typical of most living organisms. This, and its low cost, make tris one of the most common buffers in the biology/biochemistry laboratory. Tris is also used as a primary standard to standardize acid solutions for chemical analysis.

Tris is used to increase membrane permeability of cell membranes.[7]

Medical[edit]

Tris (usually known as THAM in this context) is used as alternative to sodium bicarbonate in the treatment of metabolic acidosis.[8]

See also[edit]

References[edit]

  1. ^ Gomori, G., Preparation of Buffers for Use in Enzyme Studies. Methods Enzymology., 1, 138-146 (1955).
  2. ^ El-Harakany, A.A.; Abdel Halima, F.M. and Barakat, A.O. (1984). "Dissociation constants and related thermodynamic quantities of the protonated acid form of tris-(hydroxymethyl)-aminomethane in mixtures of 2-methoxyethanol and water at different temperatures". J. Electroanal. Chem. 162 (1–2): 285–305. doi:10.1016/S0022-0728(84)80171-0. 
  3. ^ Vega, C.A.; Butler, R.A. et al. (1985). "Thermodynamics of the Dissociation of Protonated Tris(hydroxymethy1)aminomethane in 25 and 50 wt % 2-Propanol from 5 to 45 °C". J. Chem. Eng. Data 30 (4): 376–379. doi:10.1021/je00042a003. 
  4. ^ Desmarais, WT; et al. (2002). "The 1.20 Å resolution crystal structure of the aminopeptidase from Aeromonas proteolytica complexed with Tris: A tale of buffer inhibition". Structure 10 (8): 1063–1072. doi:10.1016/S0969-2126(02)00810-9. PMID 12176384. 
  5. ^ Ghalanbor, Z; et al. (2008). "Binding of Tris to Bacillus licheniformis alpha-amylase can affect its starch hydrolysis activity". Protein Peptide Lett. 15 (2): 212–214. doi:10.2174/092986608783489616. PMID 18289113. 
  6. ^ Markofsky, Sheldon B. (2000). Nitro Compounds, Aliphatic. doi:10.1002/14356007.a17_401. 
  7. ^ Irvin, R.T.; MacAlister, T.J.; Costerton, J.W. (1981). "Tris(hydroxymethyl)aminomethane Buffer Modification of Escherichia coli Outer Membrane Permeability". J. Bacteriol 145 (3): 1397–1403. 
  8. ^ Kallet, RH; Jasmer RM, Luce JM et al. (2000). "The treatment of acidosis in acute lung injury with tris-hydroxymethyl aminomethane (THAM)". American Journal of Respiratory and Critical Care Medicine 161 (4): 1149–1153. doi:10.1164/ajrccm.161.4.9906031. PMID 10764304.