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)

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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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]²²_D - 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)

L-MIMOSINE(500-44-7)Related Product Information

• VERRUCULOGEN
• Tangeretin
• REVEROMYCIN A
• MALVIDIN CHLORIDE
• TRYPROSTATIN A
• L-MIMOSINE
• 2,3-Diaminopropionic acid
• (2S)-2-Amino-3-dimethylaminopropanoic acid
• L-2,3-Diaminopropionic acid
• 3-(N-Methylamino)-L-alanine
• 4-HYDROXYPYRIDINE
• Oxamic acid
• L-Mimosine (leucenol),L-Mimosine (leucenol)
• azaleucine
• DL-MIMOSINE,DL-MIMOSINE
• BOC-L-MIMOSINE,BOC-L-MIMOSINE
• MIMOSA EXTRACT/ MIMOSINE,MIMOSA EXTRACT/ MIMOSINE
• FMOC-L-MIMOSINE,FMOC-L-MIMOSINE