Serinol

Serinol
Identifiers
CAS Number	534-03-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL116834;
ChemSpider	61591;
ECHA InfoCard	100.007.805
EC Number	208-584-0;
PubChem CID	68294;
UNII	IC94L30J8M;
CompTox Dashboard (EPA)	DTXSID2060202 ;
	InChI InChI=1S/C3H9NO2/c4-3(1-5)2-6/h3,5-6H,1-2,4H2 Key: KJJPLEZQSCZCKE-UHFFFAOYSA-N;
	SMILES C(C(CO)N)O;
Properties
Chemical formula	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) at 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

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 include alaninol, leucinol, and 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.^[1]^[2]

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

References

↑ 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.
↑ 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.
↑ 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.