CAS Number73573-88-3
SynonymsML 236B; Mevastatinum [INN-Latin]; mevastatin; Compactin (penicillium); Antibiotic ML 236B; L66 AU IUTJ EOVY2&1 H1 G2- FT6OVTJ DQ &&stereoisomer; Mevastatin (Compactin); MFCD05662341; Statin I; (+)-Compactin; ML 236 B; 2b-Methyl-8a-(2-methyl-1-oxobutoxy)mevinic acid lactone; ML-236B; 7-[1,2,6,7,8,8a-Hexahydro-2-methyl-8-(methylbutyryloxy)naphthyl]-3-hydroxyheptan-5-olide; Compactin
Molecular FormulaC23H34O5
Molecular Weight390.51
Purity≥98 (HPLC)%
Density1.1±0.1 g/cm3
Boiling Point555.0±50.0 °C at 760 mmHg
Melting Point151 °C
Appearancepowder or crystals
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 73573-88-3 |
| Catalog No. | 2A-9011426 |
| Chinese Name | 美伐他汀 |
| Synonyms | ML 236B; Mevastatinum [INN-Latin]; mevastatin; Compactin (penicillium); Antibiotic ML 236B; L66 AU IUTJ EOVY2&1 H1 G2- FT6OVTJ DQ &&stereoisomer; Mevastatin (Compactin); MFCD05662341; Statin I; (+)-Compactin; ML 236 B; 2b-Methyl-8a-(2-methyl-1-oxobutoxy)mevinic acid lactone; ML-236B; 7-[1,2,6,7,8,8a-Hexahydro-2-methyl-8-(methylbutyryloxy)naphthyl]-3-hydroxyheptan-5-olide; Compactin |
| Molecular Formula | C23H34O5 |
| Molecular Weight | 390.51 |
| Purity | ≥98 (HPLC) |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 555.0±50.0 °C at 760 mmHg |
| Melting Point | 151 °C |
| Appearance | powder or crystals |
| Water Solubility | DMSO: 20 mg/mL |
| Storage Condition | Store in an airtight container in a cool, dry plac |
| Application | Mevastatin (Compactin; ML236B) inhibits HMG-CoA reductase (HMGCR), inhibits the biosynthesis of isoprenoids, blocks isoprenylation of proteins, and reduces plasma cholesterol levels. |
| PubChem ID | 24278540 |
| MDL Number | MFCD05662341 |
| SMILES | [H][C@]12[C@H](CCC=C1C=C[C@H](C)[C@@H]2CC[C@@H]3C[C@@H](O)CC(=O)O3)OC(=O)[C@@H](C)CC |
| InChI | 1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1 |
| InChI Key | AJLFOPYRIVGYMJ-INTXDZFKSA-N |
| Beilstein/REAXYS | 1269441 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/11426_1_73573_88_3.pdf |
| Bioactivity | Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plasma cholesterol levels in humans. IC50 value: 1 nM (Ki)Target: HMGCRMevastatin induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27. Mevastatin suppresses TNF-induced NF-κB activation (IC50 = ~17 uM), which potentiates apoptosis in human myeloid leukemia cells and thus, may be useful in treating cancer. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> HMG-CoA Reductase (HMGCR) Research Areas >> Cancer References [1]. Sugazaki M, Hirotani H, Echigo S, et al. Effects of mevastatin on grafted bone in MRL/MpJ mice. Connect Tissue Res. 2010 Apr;51(2):105-12. doi: 10.3109/03008200903105098. [2]. Evangelopoulos ME, Weis J, Krüttgen A. Mevastatin-induced neurite outgrowth of neuroblastoma cells via activation of EGFR. J Neurosci Res. 2009 Jul;87(9):2138-44. doi: 10.1002/jnr.22025. [3]. W?chtersh?user A, Akoglu B, Stein J. HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2. Carcinogenesis. 2001 Jul;22(7):1061-7. [4]. Amin-Hanjani S, Stagliano NE, Yamada M, et al. Mevastatin, an HMG-CoA reductase inhibitor, reduces stroke damage and upregulates endothelial nitric oxide synthase in mice. Stroke. 2001 Apr;32(4):980-6. Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 555.0±50.0 °C at 760 mmHg Melting Point 151-153 °C Molecular Formula C23H34O5 Molecular Weight 390.513 Flash Point 186.5±23.6 °C Exact Mass 390.240631 PSA 72.83000 LogP 3.57 Vapour Pressure 0.0±3.4 mmHg at 25°C Index of Refraction 1.535 InChIKey AJLFOPYRIVGYMJ-INTXDZFKSA-N SMILES CCC(C)C(=O)OC1CCC=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C21 Storage condition 2-8°C Water Solubility DMSO: 20 mg/mL |
| Use of | Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plasma cholesterol levels in humans. IC50 value: 1 nM (Ki)Target: HMGCRMevastatin induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27. Mevastatin suppresses TNF-induced NF-κB activation (IC50 = ~17 uM), which potentiates apoptosis in human myeloid leukemia cells and thus, may be useful in treating cancer. Properties Articles53 Name mevastatin Synonym More Synonyms Mevastatin Biological Activity Description Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plasma cholesterol levels in humans. IC50 value: 1 nM (Ki)Target: HMGCRMevastatin induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27. Mevastatin suppresses TNF-induced NF-κB activation (IC50 = ~17 uM), which potentiates apoptosis in human myeloid leukemia cells and thus, may be useful in treating cancer. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> HMG-CoA Reductase (HMGCR) Research Areas >> Cancer References [4]. Amin-Hanjani S, Stagliano NE, Yamada M, et al. Mevastatin, an HMG-CoA reductase inhibitor, reduces stroke damage and upregulates endothelial nitric oxide synthase in mice. Stroke. 2001 Apr;32(4):980-6. Chemical & Physical Properties Molecular Formula C23H34O5 Exact Mass 390.240631 PSA 72.83000 Index of Refraction 1.535 InChIKey AJLFOPYRIVGYMJ-INTXDZFKSA-N |
| Transport Info | Product name: Purity: 96.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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