Serinol

Serinol is the organic compound with the formula H2NCH(CH2OH)2. A colorless solid, it is classified both as an amino alcohol and as a diol. It is structurally related to glycerol. Its name reflects the compound's relationship to the amino acid serine, from which it can be produced by hydrogenation. Other amino alcohols derived from amino acids: alaninol, leucinol, tyrosinol.

Serinol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.805
EC Number
  • 208-584-0
UNII
  • InChI=1S/C3H9NO2/c4-3(1-5)2-6/h3,5-6H,1-2,4H2
    Key: KJJPLEZQSCZCKE-UHFFFAOYSA-N
  • C(C(CO)N)O
Properties
C3H9NO2
Molar mass 91.110 g·mol−1
Appearance colorless solid
Melting point 128 °C (262 °F; 401 K)
Boiling point 115–120 °C (239–248 °F; 388–393 K) 0.06 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Biosynthetically, it is derived from dihydroxyacetone phosphate. It can be prepared in several steps starting with the condensation of nitromethane with two equivalents of formaldehyde.[1][2]

An N,O-protected form of serinol can be produced from serine.[3]

References
  1. Andreeßen, Björn; Steinbüchel, Alexander (2011). "Serinol: Small molecule - big impact". AMB Express. 1 (1): 12. doi:10.1186/2191-0855-1-12. PMC 3222319. PMID 21906364.
  2. Baxter, Ellen W.; Reitz, Allen B. (2002). "Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents". Organic Reactions. pp. 1–714. doi:10.1002/0471264180.or059.01. ISBN 0471264180.
  3. Dondoni, Alessandro; Perrone, Daniela (2000). "Synthesis of 1,1-Dimethylethyl (S)-4-Formyl-2,2-Dimethyl-3-Oxazolidinecarboxylate by Oxidation of the Alcohol". Organic Syntheses. 77: 64. doi:10.15227/orgsyn.077.0064.
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