2-Methyl-2,4-pentanediol

2-Methyl-2,4-pentanediol
Names
IUPAC name
2-Methyl-2,4-pentanediol
Other names
Hexylene glycol; Diolane; 1,1,3-Trimethyltrimethylenediol; 2,4-Dihydroxy-2-methylpentane
Identifiers
107-41-5 YesY
Abbreviations MPD
ChEBI CHEBI:62995 N
ChEMBL ChEMBL2104293 N
ChemSpider 7582 YesY
Jmol interactive 3D Image
PubChem 7870
UNII KEH0A3F75J YesY
Properties
C6H14O2
Molar mass 118.18 g·mol−1
Appearance colourless liquid
Odor mild, sweetish[1]
Density 0.92 g/mL
Melting point −40 °C (−40 °F; 233 K)
Boiling point 197 °C (387 °F; 470 K)
miscible[1]
Vapor pressure 0.05 mmHg (20°C)[1]
Hazards
Flash point 98.3 °C (208.9 °F; 371.4 K) [2]
Explosive limits 1.3%-7.4%[1]
US health exposure limits (NIOSH):
none[1]
C 25 ppm (125 mg/m3)[1]
N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

2-Methyl-2,4-pentanediol (MPD) is an organic compound with the formula (CH3)2C(OH)CH2CH(OH)CH3. This colourless liquid is a chiral diol. It is produced industrially from diacetone alcohol by hydrogenation.[3] Total European and USA production was 15000 tonnes in 2000.[4]

2-Methyl-2,4-pentanediol exists as two enantiomers, 4R(-) and 4S(+). In the Protein Data Bank, the 3-letter code "MPD" refers to the (S)-(-) enantiomer, while "MRD" is used to refer to the (R)-(+) version. Commercially sold products labeled "MPD" are often the racemate,[5] also sold as and referred to as "hexylene glycol.[6]"

Uses

The two hydroxy groups confer water solubility and the hydrocarbon portion of the molecule makes it compatible with oils, giving 2-methyl-2,4-pentanediol surfactant and emulsion-stabilizing properties. Its relatively high viscosity can be used to control the flow properties of industrial products including coatings, cleansers, solvents, and hydraulic fluids.[7] Its high viscosity is also conducive to its use as a thickening agent in many cosmetic products, and it is speculated to have anti-fungal properties.[8]

Like related diols, it forms borate esters.

Laboratory uses

In the laboratory it is a common precipitant and cryoprotectant in protein crystallography.[9] Since hexylene glycol is compatible with polar and nonpolar molecules, it competes with the solvent in a crystallography experiment causing the protein to precipitate.[10] Hexylene glycol is so effective in protein crystallography because its amphiphilic nature and small, flexible structure allows it to bind to many different locations on a protein secondary structure including alpha helices and beta sheets.[11] When hexylene glycol binds to these different locations, water is removed and the protein crystals anneal, which prevents ice formation during cryocrystallography techniques.[12] Incorporation of hexylene glycol into solution has been known to improve the resolution of X-ray diffraction making protein structures easily identifiable.[13]

References

  1. 1 2 3 4 5 6 7 "NIOSH Pocket Guide to Chemical Hazards #0328". National Institute for Occupational Safety and Health (NIOSH).
  2. CDC - NIOSH Pocket Guide to Chemical Hazards
  3. Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a01_079.pub3
  4. SIDS Initial Assessment Report for SIAM 13: Hexylene Glycol
  5. MPD at Hampton Research , MPD Product Page
  6. Hexylene Glycol at Sigma Aldrich , Hexylene Glycol Product Page
  7. Chemicalland21.com Hexylene glycol
  8. Kinnunen, T. (1991). "Antibacterial and antifungal properties of propylene glycol, and 1,3-butylene glycol in vitro". Acta Dermato-venereologica.
  9. Crystallization Techniques: Additives, Enrico Stura, University of Glasgow
  10. Dumetz, A. (2009). "Comparative Effects of Salt, Organic and Polymer Precipitants on Protein Phase Behavior and Implications for Vapor Diffusion". J. Cryst. Growth.
  11. Anand, K (2002). "An overview on 2-methyl-2,4-pentanediol in crystallization and in crystals of biological macromolecules". Acta Crystallogr.
  12. Viatcheslav, Berejnov (2006). "Thornea Effects of cryoprotectant concentration and cooling rate on vitrification of aqueous solutions". J. Appl. Crystallography.
  13. Vera, L (2006). "Strategies for Protein Crystallography". Cryst. Growth Des.
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