2-Methyl-2,4-pentanediol

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2-Methyl-2,4-pentanediol
2-Methyl-2,4-pentanediol.png
Names
Preferred IUPAC name
2-Methylpentane-2,4-diol
Other names
2-Methyl-2,4-pentanediol
Hexylene glycol
Diolane
1,1,3-Trimethyltrimethylenediol
2,4-Dihydroxy-2-methylpentane
Isol
Identifiers
3D model (JSmol)
AbbreviationsMPD
1098298
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.173 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-489-0
PubChem CID
RTECS number
  • SA0810000
UNII
UN number 1993
  • InChI=1S/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3 X mark.svgN
    Key: SVTBMSDMJJWYQN-UHFFFAOYSA-N X mark.svgN
  • CC(CC(C)(C)O)O
Properties
C6H14O2
Molar mass 118.176 g·mol−1
Appearancecolourless 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
GHS labelling: [2]
GHS-pictogram-exclam.svg
Warning
H315, H319
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364
Flash point 98.3 °C (208.9 °F; 371.4 K) [3]
Explosive limits 1.3%-7.4% [1]
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
C 25 ppm (125 mg/m3) [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [4] Total European and USA production was 15000 tonnes in 2000. [5]

Contents

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. Commercial products labeled "MPD" are usually the racemate, [6] also sold as and referred to as "hexylene glycol". [7] [8]

Uses

2-Methyl-2,4-pentanediol exhibits both surfactant and emulsion-stabilizing properties. Its relatively high viscosity and low volatility are advantageous in coatings, cleansers, cosmetics, solvents, lubricants, and hydraulic fluids. [9] Although it is an irritant at higher concentrations, it is sometimes used in skin care, hair care, soap, and eye cosmetic products at concentrations ranging from 0.1% - 25%. [10] [11]

It is biodegradable and unlikely to accumulate in the environment. [12]

Laboratory uses

In the laboratory it is a common precipitant and cryoprotectant in protein crystallography. [13] Since hexylene glycol is compatible with polar and nonpolar molecules, it competes with the solvent in a crystallography experiment causing the protein to precipitate. [14] 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. [15] When hexylene glycol binds to these different locations, water is removed and the protein crystals anneal, which prevents ice formation during cryocrystallography techniques. [16] Incorporation of hexylene glycol into solution has been known to improve the resolution of X-ray diffraction making protein structures easily identifiable. [17] Additionally hexylene glycol is not a strong denaturing agent and thus does not significantly alter the structure of a protein during the crystallography procedure. [15]

Hexylene glycol is also used as a lubricant for polishing specimens in metallography. [18]

Like related diols, it forms borate esters.

Related Research Articles

A lubricant is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, transporting foreign particles, or heating or cooling the surfaces. The property of reducing friction is known as lubricity.

<span class="mw-page-title-main">Polyethylene glycol</span> Chemical compound

Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular weight. The structure of PEG is commonly expressed as H−(O−CH2−CH2)n−OH.

<span class="mw-page-title-main">Heptane</span> Chemical compound

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.

<span class="mw-page-title-main">Synthetic oil</span> Lubricant consisting of artificially made chemical compounds

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An antifreeze is an additive which lowers the freezing point of a water-based liquid. An antifreeze mixture is used to achieve freezing-point depression for cold environments. Common antifreezes also increase the boiling point of the liquid, allowing higher coolant temperature. However, all common antifreeze additives also have lower heat capacities than water, and do reduce water's ability to act as a coolant when added to it.

<span class="mw-page-title-main">Dimethyl sulfoxide</span> Organosulfur chemical compound used as a solvent

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after DMSO makes contact with their skin.

<span class="mw-page-title-main">Acetone</span> Organic compound ((CH3)2CO); simplest ketone

Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

<span class="mw-page-title-main">Siloxane</span> Organic functional group (Si–O–Si)

In organosilicon chemistry, a siloxane is an organic compound containing a functional group of two silicon atoms bound to an oxygen atom: Si−O−Si. The parent siloxanes include the oligomeric and polymeric hydrides with the formulae H[OSiH2]nOH and [OSiH2]n. Siloxanes also include branched compounds, the defining feature of which is that each pair of silicon centres is separated by one oxygen atom. The siloxane functional group forms the backbone of silicones [−R2Si−O−SiR2−]n, the premier example of which is polydimethylsiloxane (PDMS). The functional group R3SiO− is called siloxy. Siloxanes are manmade and have many commercial and industrial applications because of the compounds’ hydrophobicity, low thermal conductivity, and high flexibility.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">Dimethyl sulfate</span> Chemical compound

Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.

<span class="mw-page-title-main">Dimethylacetamide</span> Chemical compound

Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Panthenol</span> Pair / mixture of stereoisomers

Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms, it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used in pharmaceutical and cosmetic products as a moisturizer and to improve wound healing.

Glycol ethers are a class of chemical compounds consisting of alkyl ethers that are based on glycols such as ethylene glycol or propylene glycol. They are commonly used as solvents in paints and cleaners. They have good solvent properties while having higher boiling points than the lower-molecular-weight ethers and alcohols.

<span class="mw-page-title-main">Hypromellose</span> Cellulose ether used as emulsifier or thickening agent to disperse colloids in water

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A crystallization adjutant is a material used to promote crystallization, normally in a context where a material does not crystallize naturally from a pure solution.

<span class="mw-page-title-main">Racemic crystallography</span>

Racemic crystallography is a technique used in structural biology where crystals of a protein molecule are developed from an equimolar mixture of an L-protein molecule of natural chirality and its D-protein mirror image. L-protein molecules consist of 'left-handed' L-amino acids and the achiral amino acid glycine, whereas the mirror image D-protein molecules consist of 'right-handed' D-amino acids and glycine. Typically, both the L-protein and the D-protein are prepared by total chemical synthesis.

<span class="mw-page-title-main">Protein crystallization</span>

Protein crystallization is the process of formation of a regular array of individual protein molecules stabilized by crystal contacts. If the crystal is sufficiently ordered, it will diffract. Some proteins naturally form crystalline arrays, like aquaporin in the lens of the eye.

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. "Hexylene Glycol". pubchem.ncbi.nlm.nih.gov.
  3. CDC - NIOSH Pocket Guide to Chemical Hazards
  4. Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi : 10.1002/14356007.a01_079.pub3
  5. SIDS Initial Assessment Report for SIAM 13: Hexylene Glycol
  6. MPD at Hampton Research , MPD Product Page
  7. Hexylene Glycol at Sigma Aldrich , Hexylene Glycol Product Page
  8. Hexylene Glycol at Jena Bioscience, Hexylene Glycol Product Page
  9. Chemicalland21.com Hexylene glycol
  10. Kinnunen, T. (1991). "Antibacterial and antifungal properties of propylene glycol, and 1,3-butylene glycol in vitro". Acta Dermato-Venereologica. doi: 10.2340/0001555571148150 . S2CID   13239472.
  11. R. Rietschel; J. Fowler; A. Fisher Hexylene Glycol. In Fisher's Contact Dermatitis; Holmes, M., Ed.; BC Decker Inc.: Hamilton,Ontario, 2008; pp 290
  12. Rhodia Hexylene glycol GPS Safety Summary. 2012.
  13. Crystallization Techniques: Additives, Enrico Stura, University of Glasgow
  14. Dumetz, A. (2009). "Comparative Effects of Salt, Organic and Polymer Precipitants on Protein Phase Behavior and Implications for Vapor Diffusion". J. Cryst. Growth. 9 (2): 682–691. doi:10.1021/cg700956b.
  15. 1 2 Anand, K (2002). "An overview on 2-methyl-2,4-pentanediol in crystallization and in crystals of biological macromolecules". Acta Crystallogr. 58 (10): 1722–1728. Bibcode:2002AcCrD..58.1722A. doi:10.1107/s0907444902014610. PMC   7161645 . PMID   12351894.
  16. Viatcheslav, Berejnov (2006). "Thornea Effects of cryoprotectant concentration and cooling rate on vitrification of aqueous solutions". J. Appl. Crystallogr.
  17. Vera, L (2006). "Strategies for Protein Crystallography". Cryst. Growth Des.
  18. "GreenLube". Allied High Tech. Retrieved 2023-09-23. GreenLube is a medium viscosity hexylene glycol based lubricant used for general metallographic preparation