Glycerol

Characteristics

3D model of glycerol

Glycerol is a trihydric alcohol . Its systematic name is propane-1,2,3-triol. It is a basic building block of several groups of lipids . Glycerol derivatives also play an important role in carbohydrate metabolism .

Glycerol itself is used as a cryoprotectant, a solvent, as a wetting agent in the food industry, to treat plastics and rubber, etc.

Stereochemistry

figure 1

From the spatial representation of glycerol, it is clear that the first and third carbons are not identical. Glycerol is so-called prochiral. The difference between the 1st and 3rd carbons is that after a stereospecific event that increases the CIP priority  of one over the other, this event on one carbon (specifically sn-3) results in an absolute R configuration, while a similar event on on the opposite side of the molecule (at the sn-1 carbon) of the absolute configuration S. Enzymes distinguish both positions. For example, glycerol kinase performs phosphorylation to form the R-enantiomer of glycerol phosphate. Stereospecific numbering ( stereospecific numbering, sn ) is used to mark positions.

figure 2

Links

Related Articles

• Lipid breakdown and metabolism of ketone bodies
• Triacylglycerols
• Formation of fatty acids and triacylglycerols

Reference

1. ČERVINKA, Otakar. Chirality and related concepts. Chemical Letters [online] . 1999, year 93, vol. 93, no. 5, pp. 294–305, also available from < http://www.chemicke-listy.cz/docs/full/1999_05_294-305.pdf >. ISSN 1213-7103. 
2. ↑ IUPAC. Basic Terminology of Stereochemistry  [online]. ©1996. [feeling. 3/4/2010]. < http://www.sbcs.qmul.ac.uk/iupac/stereo/NQ.html >.
3. ↑ IUPAC. Basic Terminology of Stereochemistry  [online]. ©1996. [feeling. 3/4/2010]. < http://www.sbcs.qmul.ac.uk/iupac/stereo/BC.html >.
4. ↑ IUPAC. Basic Terminology of Stereochemistry  [online]. ©1996. [feeling. 3/4/2010]. < http://www.sbcs.qmul.ac.uk/iupac/stereo/NQ.html >.
5. ↑ IUPAC. Nomenclature of Lipids  [online]. ©1976. [feeling. 3/4/2010]. < http://www.sbcs.qmul.ac.uk/iupac/lipid/lip1n2.html >.
6. ↑ Note: however, this is a special numbering method only for glycerol.