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) 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: 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.^[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.