L-MIMOSINE CAS 500-44-7
Introduction：Basic information about L-MIMOSINE CAS 500-44-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 |
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 |
| 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 Information
| Hazard Codes | Xn |
| Risk Statements | 20/21/22 |
| Safety Statements | 22-36 |
| WGK Germany | 3 |
| HS Code | 29333990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Hazardous Substances Data | 500-44-7(Hazardous Substances Data) |
| 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-proteinplant 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 Preparation Products And Raw materials
