500-62-9

Basic information

• Product Name: YANGONIN
• Synonyms: YANGONIN;11-METHOXYYANGONIN;4-methoxy-6-(beta-(p-anisyl)vinyl)-alpha-pyrone;4-methoxy-6-(p-methoxystyryl)-2h-pyran-2-on;4-methoxy-6-(p-methoxystyryl)-2h-pyran-2-one;5-hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoicacidgamma-lacton;4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one;4-Methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one
• CAS NO: 500-62-9
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27
• Product Categories: Aromatics;Heterocycles;Mutagenesis Research Chemicals
• Mol File: 500-62-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 155-157°
• Boiling Point: 487.6 °C at 760 mmHg
• Flash Point: 219.8 °C
• Appearance: pale yellow powder
• Density: 1.2 g/cm³
• Vapor Pressure: 1.18E-09mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• BRN: 230710
• CAS DataBase Reference: YANGONIN(CAS DataBase Reference)
• NIST Chemistry Reference: YANGONIN(500-62-9)
• EPA Substance Registry System: YANGONIN(500-62-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 500-62-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 500-62-9 differently. You can refer to the following data:
1. A lactone isolated from the Kava plant (Piper methysticum). The active constituents of Kava are a group of approx. 18 compounds collectively referred to as kavalactones or kava pyrones. Kawain, dihydrokawain, methysticin, dihydromethysticin, yangonin, and desmethoxyyangonin are the six major kavalactones. Kava beverages and other preparations are known to be anxiolytic and are used for anxiety disorders. Dietary supplements containing the root of the kava shrub have been implicated in several cases of liver toxicity in humans, including several who required liver transplants after using kava supplements.
2. A lactone isolated from the Kava plant (Piper methysticum). rokawain, methysticin, dihydromethysticin, yangonin, and desmethoxyyangonin are the six major kavalactones. Kava beverages and other preparations are known to be anxiolytic and are used for anxiety d isorders. a supplements.

Description

Yangonin is a natural kavalactone from the kava plant, P. methysticum. It enhances the binding of bicuculline at the γ-amino butyric acid (GABA) receptor GABAA at 1.0 μM. Yangonin also binds the central cannabinoid (CB1) receptor with a Ki value of 0.72 μM, but whether it serves as an agonist or antagonist at this receptor remains to be determined. Yangonin blocks the activation of NF-κB by TNF-α. It also inhibits anchorage-dependent and independent growth of bladder cancer cell lines through induction of autophagic cell death (IC50s = 15-59 mg/mL).

InChI:InChI=1/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+

Synthetic route

4-methoxy-6-vinyl-2H-pyran-2-one (1334928-11-8) + 4-methoxybenzenediazonium tetrafluoroborate (459-64-3) → yangonin (500-62-9)

Conditions	Yield
Stage #1: 4-methoxy-6-vinyl-2H-pyran-2-one With sodium acetate; palladium diacetate In acetonitrile for 0.166667h; Heck-Matsuda reaction; Stage #2: 4-methoxybenzenediazonium tetrafluoroborate In acetonitrile Heck-Matsuda reaction;	96%

(4-Methoxy-2-oxo-2H-pyran-6-yl)methyltriphenylphosphonium Bromide (54108-46-2) + 4-methoxy-benzaldehyde (123-11-5) → yangonin (500-62-9)

Conditions	Yield
With sodium ethanolate In ethanol; N,N-dimethyl-formamide for 16h; Ambient temperature;	95%

(E)-4-methoxy-6-(4-methoxystyryl)-5,6-dihydro-2H-pyran-2-one (3155-49-5, 3328-60-7, 62445-12-9, 130464-78-7) → yangonin (500-62-9)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 2h; Inert atmosphere; Reflux;	85%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 2h; Inert atmosphere; Reflux;	85%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 2h; Reflux;	80%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 0.5h; Reflux;	303.5 mg

4-hydroxy-6-(4-methoxy-styryl)-pyran-2-one (361433-25-2) + dimethyl sulfate (77-78-1) → yangonin (500-62-9)

Conditions	Yield
With triisopropylamine In dichloromethane at -78 - 20℃; for 2h;	65%

4-methoxy-6-methyl-2H-pyran-2-one (672-89-9) + 4-methoxy-benzaldehyde (123-11-5) → yangonin (500-62-9)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 25℃; for 48h; Aldol Condensation;	61%
With magnesium methanolate Inert atmosphere; Reflux;	59%
With magnesium In methanol for 4h; Reflux;	30%

diazomethane (186581-53-3, 908094-01-9) + 6-(4-methoxy-trans-styryl)-pyran-2,4-dione (501-57-5) → 2-methoxy-6-<2-(4-methoxyphenyl)ethenyl>pyran-4-one (101-35-9) + yangonin (500-62-9)

Conditions	Yield
With diethyl ether

4-hydroxy-6-(4-methoxy-styryl)-pyran-2-one (361433-25-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 18h; Ambient temperature; Yield given;

+ 4-methoxy-benzenediazonium-(1)-chloride-solution

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) COCl2, 2.) triethylamine / 1.) RT, 18 h, 2.) petroleum ether, CH2Cl2, 0 deg C, 30 min 2: 53 percent / 60 percent NaH, 1.46 M n-BuLi / tetrahydrofuran; hexane / 20 min, rt; 0 deg C, 10 min; 0 deg C, 1-2 h 3: 1.) TFA, 2.) acetic anhydride / 1.) CH2Cl2, rt, 1 h, 2.) rt, 18 h 4: K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme

→ yangonin

Conditions	Yield
Multi-step reaction with 3 steps 1: 53 percent / 60 percent NaH, 1.46 M n-BuLi / tetrahydrofuran; hexane / 20 min, rt; 0 deg C, 10 min; 0 deg C, 1-2 h 2: 1.) TFA, 2.) acetic anhydride / 1.) CH2Cl2, rt, 1 h, 2.) rt, 18 h 3: K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme

(E)-tert-butyl 3,5-dioxo-7-(p-methoxyphenyl)hept-6-enoate (157287-08-6) → yangonin (500-62-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) TFA, 2.) acetic anhydride / 1.) CH2Cl2, rt, 1 h, 2.) rt, 18 h 2: K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme

6-(bromomethyl)-4-methyl-2H-pyran-2-one (54108-45-1) → yangonin (500-62-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / benzene / 16 h / Heating 2: 95 percent / sodium ethoxide / dimethylformamide; ethanol / 16 h / Ambient temperature View Scheme

4-hydroxy-6-methyl-2-pyron (675-10-5) → yangonin (500-62-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / Inert atmosphere; Reflux 2: selenium(IV) oxide / 1,4-dioxane / 5 h / 180 °C / Inert atmosphere; Sealed tube 3: n-butyllithium; methyl-triphenylphosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere 4: sodium acetate; palladium diacetate / acetonitrile / 0.17 h View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 20 °C 2: magnesium methanolate / methanol / 60 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 20 °C 2: magnesium methanolate / Inert atmosphere; Reflux View Scheme

4-methoxy-6-methyl-2H-pyran-2-one (672-89-9) → yangonin (500-62-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane / 5 h / 180 °C / Inert atmosphere; Sealed tube 2: n-butyllithium; methyl-triphenylphosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere 3: sodium acetate; palladium diacetate / acetonitrile / 0.17 h View Scheme

4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one (1092383-57-7) → yangonin (500-62-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Pd2(dba)4; sodium acetate / 1 h / 80 °C / Microwave irradiation 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Inert atmosphere; Reflux View Scheme

Upstream product

• 186581-53-3 diazomethane 
• 501-57-5 6-(4-methoxy-trans-styryl)-pyran-2,4-dione 
• 54108-46-2 (4-Methoxy-2-oxo-2H-pyran-6-yl)methyltriphenylphosphonium Bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 361433-25-2 4-hydroxy-6-(4-methoxy-styryl)-pyran-2-one 
• 74-88-4 methyl iodide 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 157287-05-3 (E)-N-(p-methoxycinnamoyl)-2-methylaziridine 
• 157287-08-6 (E)-tert-butyl 3,5-dioxo-7-(p-methoxyphenyl)hept-6-enoate 
• 54108-45-1 6-(bromomethyl)-4-methyl-2H-pyran-2-one 
• 3155-49-5 (E)-4-methoxy-6-(4-methoxystyryl)-5,6-dihydro-2H-pyran-2-one 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 672-89-9 4-methoxy-6-methyl-2H-pyran-2-one 
• 1092383-57-7 4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one 

Downstream Products

• 3155-52-0 4-methoxy-6-(p-methoxyphenethyl)-2H-pyran-2-one 
• 7639-27-2 (E)-6-(4-hydroxystyryl)-4-methoxy-2H-pyran-2-one 

Relevant articles and documents

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Iterative polyketide synthesis via a consecutive carbonyl-protecting strategy

To address the difficulty in protecting a β-polycarbonyl compound, a method for the sequential protection of elongating carbonyl groups was demonstrated. The iterative chain elongation of a carboxylic acid with malonic acid half thioester followed by the protection of the resulting β-ketothioester was performed via the stepwise formation of an isoxazole ring using an O-protected oxime functionality. Yangonin and isosakuranetin were synthesized according to this procedure.

BONE METABOLISM IMPROVER

PROBLEM TO BE SOLVED: To provide an agent and food/drink having osteoclast differentiation inhibitory action and osteoblast differentiation promoting action and useful against osteoporosis. SOLUTION: The present invention provides an osteoblast differentiation promoter or osteoclast differentiation inhibitor containing a kawalactone derivative compound as an active ingredient, and an agent for preventing or improving osteoporosis or rheumatoid arthritis that contains the same. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT