Glycerol

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Glycerol


Chemical name Propane-1,2,3-triol
Other names glycerin
glycerine
propane-1,2,3-triol
1,2,3-propanetriol
1,2,3-trihydroxypropane
glyceritol
glycyl alcohol
Chemical formula C3H5(OH)3
Molecular mass 92.09382 g/mol
CAS number [56-81-5]
HS number Crude: 1520.00.00
Pure: 2905.45.00
Density 1.261 g/cm³
Viscosity 1.5 Pa.s
Melting point 18 °C (64.4°F)
Boiling point 290 °C (554°F)
Food energy 4.32 kcal/g
SMILES OCC(O)CO
Flash Point 160 °C (closed cup)
Supplementary data page
Structure & properties n, εr, etc.
Thermodynamic data Phase behavior
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Disclaimer and references

Glycerol is a chemical compound with the formula HOCH2CH(OH)CH2OH. This colorless, odorless, viscous liquid is widely used in pharmaceutical formulations. Also commonly called glycerin or glycerine, it is a sugar alcohol and fittingly is sweet-tasting and of low toxicity. Glycerol has three hydrophilic alcoholic hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. Its surface tension is 64.00 mN/m at 20 °C and it has a temperature coefficient of -0.0598 mN/(m K). It is a central component of lipids.

Contents

  • 1 Synthesis
  • 2 Metabolism
  • 3 Applications
    • 3.1 Medicine and pharmaceutical technology
    • 3.2 Personal care
    • 3.3 Foods and beverages
    • 3.4 Feed
    • 3.5 Polyether polyols
    • 3.6 Alkyd resins (plastics) and cellophane
    • 3.7 Absolute alcohol
    • 3.8 Other applications
  • 4 Danger of contamination with diethylene glycol
  • 5 See also
  • 6 References
  • 7 External links

[edit] Synthesis

Glycerol (3D model), showing the atoms and the lone electron pairs associated with the oxygen atoms (in pink)

Since glycerol forms the backbone of triglycerides, it is produced on saponification or transesterification. Soap making and biodiesel production are examples of the former and latter. Until recently, synthetic glycerol was mainly manufactured at an industrial scale from epichlorohydrin though this process is no longer economical. Glycerol is a 10% by-product of biodiesel manufacture (via the transesterification of vegetable oils). This has led to a glut of crude glycerol on the market. Although this crude glycerol (typically containing 20% water and residual esterification catalyst) can be refined to a purified form, a great deal of research is being conducted to try to make value-added molecules from glycerol, as an alternative to incineration. One such programme to add value to this glut of glycerol is the UK-based initiative The Glycerol Challenge. Some potential uses for glycerol include the following:

[edit] Metabolism

Glycerol is a precursor for synthesis of triacylglycerols and of phospholipids in the liver and adipose tissue. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. The glycerol component can be converted to glucose by the liver and provides energy for cellular metabolism.

Before glycerol can enter the pathway of glycolysis or gluconeogenesis (depending on physiological conditions), it must be converted to their intermediate glyceraldehyde 3-phosphate in the following steps:

Glycerol Glycerol kinase Glycerol-3-phosphate Glycerol-3-phosphate dehydrogenase Dihydroxyacetone phosphate Triosephosphate isomerase Glyceraldehyde 3-phosphate
ATP ADP NAD+ NADH
+ H+
NADH
+ H+
NAD+

The enzyme glycerol kinase is present only in the liver. In adipose tissue, glycerol 3-phosphate is obtained from dihydroxyacetone phosphate (DHAP) with the enzyme glycerol-3-phosphate dehydrogenase.

[edit] Applications

[edit] Medicine and pharmaceutical technology

[edit] Personal care

It was once believed that when used as an emollient, glycerol should never be applied undiluted to the skin. It was thought that the same powerful hygroscopic property that draws moisture out of the air to moisten the skin will draw moisture out of the skin if the glycerol is too concentrated. This in fact has proven to be untrue.[citation needed]

[edit] Foods and beverages

Glycerol has approximately 27 calories per teaspoon and is 60% as sweet as sucrose. Although it has about the same food energy as table sugar, it does not raise blood sugar levels, nor does it feed the bacteria that form plaques and cause dental cavities. Glycerol should not be consumed undiluted, as unhydrated glycerol will draw water from tissues, causing blistering in the mouth and gastric distress. As food additive, glycerol is also known as E number E422.

[edit] Feed

Glycerol is increasingly used in feeding animals.[citation needed]

[edit] Polyether polyols

[edit] Alkyd resins (plastics) and cellophane

[edit] Absolute alcohol

[edit] Other applications

Use a mixture of one part glycerol to two parts water. Place the mixture in a flat pan, and totally submerge the leaves in a single layer in the liquid. You'll have to weigh them down to keep them submerged. In two to six days, they should have absorbed the liquid and be soft and pliable. Remove them from the pan and wipe off all the liquid with a soft cloth. Done correctly, the leaves will remain soft and pliable indefinitely.

[edit] Danger of contamination with diethylene glycol

On May 4, 2007, the US Food and Drug Administration advised all US makers of medicines to test all batches of glycerine for the toxic diethylene glycol.[12] This follows an occurrence of 100 fatal poisonings in Panama resulting from a Chinese factory deliberately falsifying records in order to export the cheaper diethylene glycol as the more expensive glycerol.[13] Glycerine and diethylene glycol are similar in appearance, smell, and taste. The US Federal Food, Drug, and Cosmetic Act was passed following the 1937 "Elixir Sulfanilamide" incident of poisoning caused by diethylene glycol contamination of medicine.