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D-Prolinol.svg L-Prolinol.svg
CAS number 68832-13-3 (D-prolinol) YesY, 23356-96-9 (L-prolinol)
PubChem 2724541 (D-prolinol), 640091 (L-prolinol)
ChemSpider 2006673 (D-prolinol), 555468 (L-prolinol)
Jmol-3D images Image 1
Image 2
Molecular formula C5H11NO
Molar mass 101.15 g/mol
Appearance Liquid
Density 1.036 g/mL liquid
Boiling point 74-76 °C at 2 mmHg
R-phrases 36/37/38
S-phrases 26-36
Main hazards Irritant
Flash point 86 °C (187 °F; 359 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Prolinol is a chiral amino-alcohol that is used as a chiral building block in organic synthesis. It exists as two enantiomers: the D and L forms.


Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.[1][2] Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.


Prolinol is used in broad variety of chemical reactions as chiral ligand, chiral catalyst or chiral auxiliary reagent in the Hajos-Parrish-Eder-Sauer-Wiechert reaction, the Baylis-Hillman reaction, Noyori type reaction and the Michael reaction. [3][4]

See also[edit]


  1. ^ Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Reduction of α-Amino Acids: L-Valinol Organic Syntheses, Collected Volume 7, p.530 (1990).
  2. ^ Enders D.; Fey P.; Kipphardt, H. [1] Organic Syntheses, Collected Volume 8, p.26 (1993).
  3. ^ Benjamin List (2002). "Proline-catalyzed asymmetric reactions". Tetrahedron 58 (28): 5573–5590. doi:10.1016/S0040-4020(02)00516-1. 
  4. ^ Shinichi Itsuno, Koichi Ito, Akira Hirao and Seiichi Nakahama (1984). "Asymmetric synthesis using chirally modified borohydrides. Part 2. Enantioselective reduction of ketones with polymeric (S)-prolinol–borane reagent". J. Chem. Soc., Perkin Trans. 1 (12): 2887–2895. doi:10.1039/P19840002887.