Mimosine

Mimosine

Names
IUPAC name (2S)-2-Amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
Other names leucenol
Identifiers
CAS Number	500-44-7 N
3D model (JSmol)	Interactive image
ECHA InfoCard	100.007.187
PubChem CID	440473
CompTox Dashboard (EPA)	DTXSID401017244
SMILES C1=CN(C=C(C1=O)O)C[C@@H](C(=O)O)N
Properties
Chemical formula	C8H10N2O4
Molar mass	198.178 g·mol−1
Melting point	291 °C (556 °F; 564 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Mimosine is an alkaloid, β-3-hydroxy-4 pyridone amino acid. It is a toxic non-protein free amino acid otherwise chemically similar to tyrosine, and was first isolated from Mimosa pudica. In ruminants, mimosine is degraded to 3,4 and 2,3 dihydroxy pyridone (3,4- and 2,3-DHP). It occurs in a few other Mimosa spp. and all members of the closely related genus Leucaena. Mimosine arrests dividing cells in the late G1 phase by inhibiting DNA replication initiation.

Although toxicosis has occurred in Australia, Papua New Guinea, Africa and Florida, it has not been recorded in any other tropical and subtropical regions. Goats in Burma lost hair when fed to diet containing 50 % of Leucaena. Goats and cattle in Hawaii are able to degrade the 3,4-DHP ruminally. Tolerance might be related to the presence or absence of microbes tolerant to mimosine and 3,4-DHP. It is known that at least Australian goats do not share the abilities of their Hawaiian counterparts.

Leucenol

This was first isolated from the seeds of Leucaena glauca Benth., and was later investigated by Adams and coworkers. It melts with decomposition. B•HCl melts 174.5-5.0 °C, with decomposition; B•HBr 179.5 °C (dec.), B•HI 183.0-3.5 °C (dec.). Leucenol only forms monobasic acids, but the methyl esther forms a dihydrochloride, C₇H₉O₂N₂(COOMe)•2 HCl•½ H₂O, mp. 175-6 °C. Bickel and Wibaut found in feeding experiments with rats and mice that leucenol is probably the toxic constituent of Leucaena glauca seeds, but they did not observe with these animals the loss of hair which seems to occur when these seeds are fed to cattle. Aung from Myanmar isolated the new subspecies of K. pneumonae that can degrade mimosine.