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L-MIMOSINE

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L-MIMOSINE Basic information

Product Name:
L-MIMOSINE
Synonyms:
  • L-LEUCININE
  • L(-)-MIMOSINE
  • L-MIMOSINE
  • BETA-[N-(3-HYDROXY-4-PYRIDONE)]-ALPHA-AMINOPROPIONIC ACID
  • LEUCENOL
  • ALPHA-AMINO-BETA-[N-(3-HYDROXY-4-PYRIDONE)]-PROPIONIC ACID
  • MIMOSINE
  • (S)-ALPHA-AMINO-BETA-(1-[3-HYDROXY-4-OXOPYRIDINE])PROPIONIC ACID
CAS:
500-44-7
MF:
C8H10N2O4
MW:
198.18
EINECS:
207-905-1
Product Categories:
  • Inhibitors
  • Alkaloids
Mol File:
500-44-7.mol
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L-MIMOSINE Chemical Properties

Melting point:
224-228 °C
Boiling point:
335.48°C (rough estimate)
Density 
1.3764 (rough estimate)
refractive index 
1.6180 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Water (Slightly, Heated, Sonicated)
form 
Pink to brown powder.
pka
2.06±0.10(Predicted)
color 
White to Off-White
Merck 
13,6221
InChIKey
WZNJWVWKTVETCG-YFKPBYRVSA-N
LogP
-1.080 (est)
CAS DataBase Reference
500-44-7(CAS DataBase Reference)
EPA Substance Registry System
Mimosine (500-44-7)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
22-36
WGK Germany 
3
HS Code 
29333990
Hazardous Substances Data
500-44-7(Hazardous Substances Data)

MSDS

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L-MIMOSINE Usage And Synthesis

Description

This alkaloid was isolated by Renz from Mimosia pudica L. and also from Leucaena glauca Benth. It is laevorotatory with [α]22D - 21 ° (H20) and yields a blue, crystalline copper salt. On heating the chloride under pressure, a sublimate is formed which has been shown, by comparison with a synthetic specimen, to be N-methyl-3-hydroxypyrid-4-one, m.p. 224°C. The alkaloid is toxic and in horses produces loss of hair when administered in large doses.

Chemical Properties

light tan to pink crystalline powder

Uses

L-Mimosine from Koa hoale seeds has been used to study its anti-inflammatory effect in chronic inflammatory response (potassium permanganate - induced chronic granuloma).

Definition

ChEBI: An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.

General Description

L-mimosine [β-N (3-hydroxy-4-pyridone)-α-amino propionic acid] is a non-protein amino acid and is a vital component of tropical legumes, such as Leucaena glauca and other legumes belonging to Mimosa spp. Structurally L-mimosine resembles dihydroxyphenylalanine except 3,4-dihydroxy-phenyl ring replaced by 3-hydroxy-4-pyridone ring.

Biochem/physiol Actions

L-Mimosine is a plant amino acid and potential inhibitor of the cell cycle giving rise to growth arrest in G1-phase. It is an iron chelator that inhibits DNA replication in mammalian cells. L-Mimosine has been shown to promote apoptosis in xenotransplanted human pancreatic cancer. L-Mimosine stabilizes hypoxia inducible factor 1 (HIF-1) and stimulates the expression of B-cell translocation gene 2 (Btg2) and N-myc downstream regulated gene 1 (Ndrg1) at the transcriptional level, which reduce cell proliferation of prostate carcinoma cells in vitro. L-Mimosine stabilizes HIF-1 through the inhibition of prolyl hydroxylases (PHDs) which target HIF-1 through degradation. The mechanism of inhibition is likely through the chelation of Fe2+ bound to the active site of PHD which is required for enzymatic activity. Mimosine inhibits cell cycle progression via iron chelation in MDA-MB-453 human breast cancer cells. Mimosine, hinder folate metabolism in cell-specific manner.

References

Renz., Zeit. physiol. Chem., 244, 153 (1936)
Nienburg, Taubock., ibid, 250,80 (1937)
Kostermanns., Rec. trav. Chim. Pays-Bas, 65, 319 (1946)
Kostermann., ibid, 66,93 (1947)

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