Aminoacetaldehyde

Last updated
Aminoacetaldehyde
Aminoacetaldehyde.png
Names
Preferred IUPAC name
Aminoacetaldehyde
Other names
H-Gly-al; glycynal
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C2H5NO/c3-1-2-4/h2H,1,3H2
    Key: LYIIBVSRGJSHAV-UHFFFAOYSA-N
  • C(C=O)N
Properties
C2H5NO
Molar mass 59.068 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Aminoacetaldehyde is the organic compound with the formula OHCCH2NH2. Under the usual laboratory conditions, it is unstable, tending instead to undergo self-condensation. [1] Aminoacetaldehyde diethylacetal is a stable surrogate. [2]

In nature, aminoacetaldehyde is produced by oxygenation of taurine catalyzed by taurine dioxygenase, which produces the sulfite H2NCH2CH(OH)SO3.

See also

Related Research Articles

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Taurine Biologically significant aminosulfonic acid

Taurine, or 2-aminoethanesulfonic acid, is an organic compound that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight. It is named after the Latin taurus which means bull or ox, as it was first isolated from ox bile in 1827 by German scientists Friedrich Tiedemann and Leopold Gmelin. It was discovered in human bile in 1846 by Edmund Ronalds.

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Aminoacetone Chemical compound

Aminoacetone is the organic compound with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms stable salts, e.g. aminoacetone hydrochloride ([CH3C(O)CH2NH3]Cl)). The semicarbazone of the hydrochloride is another bench-stable precursor. Aminoacetone is a metabolite that is implicated in the biosynthesis of methylglyoxal.

In enzymology, a taurine dioxygenase (EC 1.14.11.17) is an enzyme that catalyzes the chemical reaction

Neber rearrangement

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Hypotaurine Chemical compound

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Aminoacetaldehyde diethylacetal Chemical compound

Aminoacetaldehyde diethylacetal is the organic compound with the formula (EtO)2CHCH2NH2. A colorless liquid, it is used as a surrogate for aminoacetaldehyde.

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References

  1. Fisher, Lawrence E.; Muchowski, Joseph M. (1990). "Synthesis of α-Aminoaldehydes and α-Aminoketone. A Review". Organic Preparations and Procedures International. 22 (4): 399–484. doi:10.1080/00304949009356309.
  2. Amato, Francesco; Marcaccini, Stefano (2005). "2,2-Diethoxy-1-Isocyanoethane". Organic Syntheses. 82: 18. doi: 10.15227/orgsyn.082.0018 .