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HomeProduct name listL-MIMOSINE

L-MIMOSINE

Synonym(s):(S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid;Leucenol

  • CAS NO.:500-44-7
  • Empirical Formula: C8H10N2O4
  • Molecular Weight: 198.18
  • MDL number: MFCD00075909
  • EINECS: 207-905-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:07:02
L-MIMOSINE Structural

What is L-MIMOSINE?

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

The Uses of L-MIMOSINE

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

What are the applications of Application

L-Mimosine is a rare plant non-protein toxic amino acid

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)

Properties of L-MIMOSINE

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
CAS DataBase Reference 500-44-7(CAS DataBase Reference)
EPA Substance Registry System Mimosine (500-44-7)

Safety information for L-MIMOSINE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

Computed Descriptors for L-MIMOSINE

InChIKey WZNJWVWKTVETCG-YFKPBYRVSA-N

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