Misplaced Pages

Serinol

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Serinol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.805 Edit this at Wikidata
EC Number
  • 208-584-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H9NO2/c4-3(1-5)2-6/h3,5-6H,1-2,4H2Key: KJJPLEZQSCZCKE-UHFFFAOYSA-N
SMILES
  • C(C(CO)N)O
Properties
Chemical formula C3H9NO2
Molar mass 91.110 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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.

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.

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

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.
Categories: