CAS Number500-62-9
Synonyms4-Methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one; 5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic Acid d-Lactone; 4-Méthoxy-6-[(E)-2-(4-méthoxyphényl)éthènyl]-2H-pyran-2-one; 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-Methoxy-6-((E)-4-methoxystyryl)pyran-2-one; 4-Methoxy-6-[b-(p-anisyl)vinyl]-a-pyrone; 6-(p-Methoxystyryl)-4-methoxy-a-pyrone; Yangonin; (E)-4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
Molecular FormulaC15H14O4
Molecular Weight258.27
Purity≥95.0 (HPLC)%
Density1.2±0.1 g/cm3
Boiling Point487.6±45.0 °C at 760 mmHg
Melting Point155-157ºC
AppearanceLight yellow powder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 500-62-9 |
| Catalog No. | 2A-9022308 |
| Chinese Name | 甲氧醉椒素 |
| Synonyms | 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one; 5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic Acid d-Lactone; 4-Méthoxy-6-[(E)-2-(4-méthoxyphényl)éthènyl]-2H-pyran-2-one; 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-Methoxy-6-((E)-4-methoxystyryl)pyran-2-one; 4-Methoxy-6-[b-(p-anisyl)vinyl]-a-pyrone; 6-(p-Methoxystyryl)-4-methoxy-a-pyrone; Yangonin; (E)-4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one |
| Molecular Formula | C15H14O4 |
| Molecular Weight | 258.27 |
| Purity | ≥95.0 (HPLC) |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 487.6±45.0 °C at 760 mmHg |
| Melting Point | 155-157ºC |
| Appearance | Light yellow powder |
| Storage Condition | 2-8°C |
| Application | Yangonin has high affinity for the human recombinant cannabinoid CB1 receptor, with IC50 and Ki of 1.79±0.53 μM and 0.72±0.21 μM, respectively. |
| HTC | 2932999099 |
| MDL Number | MFCD00221733 |
| SMILES | COc1ccc(cc1)\C=C\C2=CC(OC)=CC(=O)O2 |
| InChI | 1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+ |
| InChI Key | XLHIYUYCSMZCCC-VMPITWQZSA-N |
| Beilstein/REAXYS | 230710 |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | Transport |
| MSDS | msds/22308_1_500_62_9.pdf |
| Bioactivity | Yangonin exhibits affinity for the human recombinant cannabinoid CB1 receptor with an IC50 and a Ki of 1.79 ± 0.53 μM and 0.72±0.21 μM, respectively. Related Catalog Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Research Areas >> Inflammation/Immunology Natural Products >> Others Target CB1 Receptor:1.79 μM (IC50) CB1 Receptor:0.72 μM (Ki) RelA In Vitro Yangonin is one of the six major kavalactones found in Piper methysticum.Yangonin potently inhibits NF-κB activation through suppression of the transcriptional activity of the RelA/p65 subunit of NF-κB. Yangonin significantly inhibits the induced expression of the NF-κB-reporter gene. However, Yangonin does not interfere with TNF-α-induced inhibitor of κBα (IκBα) degradation, p65 nuclear translocation, and DNA-binding activity of NF-κB. Yangonin inhibits not only the induced NF-κB activation by overexpression of RelA/p65, but also transactivation activity of RelA/p65. Yangonin does not inhibit TNF-α-induced activation of p38, but it significantly impairs activation of ERK 1/2 and stress-activated protein kinase/JNK[2]. Cell Assay HeLa cells are seeded at 1×105 cells/mL in 96-well plates containing 100 μL of DMEM medium with 10% FBS and incubated overnight. Yangonin is dissolved in DMSO and DMSO is added to all plates to compensate the same volume of DMSO. After 24 h, the cells are pretreated with different concentrations of Yangonin (0.1-3 μM) for 1 h, followed by stimulation with or without TNF-α for 24 h. Subsequently, cells are cultured with MTT solution (5 mg/mL) for 3 h. The viable cells convert MTT to formazan, which generates a blue-purple color after dissolving in 150 μL of DMSO. The absorbance at 570 nm is measured by an ELISA plate reader[2]. References [1]. Ligresti A, et al. Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB1 receptor ligand. Pharmacol Res. 2012 Aug;66(2):163-9. [2]. Ma J, et al. Yangonin blocks tumor necrosis factor-α-induced nuclear factor-κB-dependent transcription by inhibiting the transactivation potential of the RelA/p65 subunit. J Pharmacol Sci. 2012;118(4):447-54. [3]. Wruck CJ, et al. Kavalactones protect neural cells against amyloid beta peptide-induced neurotoxicity via extracellular signal-regulated kinase 1/2-dependent nuclear factor erythroid 2-related factor 2 activation. Mol Pharmacol. 2008 Jun;73(6):1785-95. Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 487.6±45.0 °C at 760 mmHg Melting Point 155-157ºC Molecular Formula C15H14O4 Molecular Weight 258.269 Flash Point 219.7±28.8 °C Exact Mass 258.089203 PSA 48.67000 LogP 1.75 Vapour Pressure 0.0±1.2 mmHg at 25°C Index of Refraction 1.578 InChIKey XLHIYUYCSMZCCC-VMPITWQZSA-N SMILES COc1ccc(C=Cc2cc(OC)cc(=O)o2)cc1 Storage condition 2-8°C |
| Use of | Properties Articles15 Name yangonin Synonym More Synonyms Yangonin Biological Activity Related Catalog Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Research Areas >> Inflammation/Immunology Natural Products >> Others CB1 Receptor:1.79 μM (IC50) CB1 Receptor:0.72 μM (Ki) References [1]. Ligresti A, et al. Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB1 receptor ligand. Pharmacol Res. 2012 Aug;66(2):163-9. [2]. Ma J, et al. Yangonin blocks tumor necrosis factor-α-induced nuclear factor-κB-dependent transcription by inhibiting the transactivation potential of the RelA/p65 subunit. J Pharmacol Sci. 2012;118(4):447-54. Chemical & Physical Properties Molecular Formula C15H14O4 Exact Mass 258.089203 PSA 48.67000 Index of Refraction 1.578 InChIKey XLHIYUYCSMZCCC-VMPITWQZSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| 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 United Nations shipping name 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 Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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