| Identification | More | [Name]
L-MIMOSINE | [CAS]
500-44-7 | [Synonyms]
ALPHA-AMINO-BETA-[N-(3-HYDROXY-4-PYRIDONE)]-PROPIONIC ACID
BETA-[N-(3-HYDROXY-4-PYRIDONE)]-ALPHA-AMINOPROPIONIC ACID
LEUCENOL
L-LEUCININE
L(-)-MIMOSINE
L-MIMOSINE
MIMOSINE
(S)-ALPHA-AMINO-BETA-(1-[3-HYDROXY-4-OXOPYRIDINE])PROPIONIC ACID
(s)-1(4h)-pyridinepropanoicaci
leucenine
(S)-alpha-amino-3-hydroxy-4-oxo-1(4H)-pyridylpropionic acid
MIMOSINE, 98% (LEUCENOL, OPTICALLY ACTIV E)
L-MIMOSINE FROM KOA HOALE SEEDS
(s)-α-amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid
MIMOSINE extrapure for biochemistry
L-Mimosine from Koa hoale seeds, Leucenol, optically active, Leucenol, α-Amino-β-(N-[3-hydroxy-4-pyridone])propionic acid:
Leucenol, (S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid
Mimosine 99%
[αR,(+)]-α-Amino-3-hydroxy-4-oxo-1(4H)-pyridinepropionic acid | [EINECS(EC#)]
207-905-1 | [Molecular Formula]
C8H10N2O4 | [MDL Number]
MFCD00075909 | [Molecular Weight]
198.18 | [MOL File]
500-44-7.mol |
| Chemical Properties | Back Directory | [Appearance]
light tan to pink crystalline powder | [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 | [InChI]
InChI=1/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/s3 | [InChIKey]
WZNJWVWKTVETCG-YFKPBYRVSA-N | [SMILES]
C(N1C=CC(=O)C(O)=C1)[C@H](N)C(=O)O |&1:9,r| | [LogP]
-1.080 (est) | [CAS DataBase Reference]
500-44-7(CAS DataBase Reference) | [EPA Substance Registry System]
Mimosine (500-44-7) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29333990 | [Hazardous Substances Data]
500-44-7(Hazardous Substances Data) |
| Hazard Information | Back Directory | [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. | [storage]
Desiccate at -20°C | [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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