YANGONIN

Base Information

• Chemical Name: YANGONIN
• CAS No.: 500-62-9
• Molecular Formula: C15H14O4
• Molecular Weight: 258.274
• Hs Code.: 2932999099
• Mol file: 500-62-9.mol

Synonyms:2H-Pyran-2-one,4-methoxy-6-(p-methoxystyryl)- (8CI);2H-Pyran-2-one,4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-, (E)-;Yangonin (6CI);4-Methoxy-6-[b-(p-anisyl)vinyl]-a-pyrone;6-(p-Methoxystyryl)-4-methoxy-a-pyrone;

Chemical Property of YANGONIN

Chemical Property:

• Appearance/Colour: pale yellow powder
• Vapor Pressure: 1.18E-09mmHg at 25°C
• Melting Point: 155-157 °C
• Refractive Index: 1.577
• Boiling Point: 487.6 °C at 760 mmHg
• Flash Point: 219.8 °C
• PSA: 48.67000
• Density: 1.2 g/cm³
• LogP: 2.82740
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Yangonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 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. 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).

Technology Process of YANGONIN

There total 20 articles about YANGONIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

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

Guidance literature:

4-methoxy-6-vinyl-2H-pyran-2-one; With sodium acetate; palladium diacetate; In acetonitrile; for 0.166667h;

4-methoxybenzenediazonium tetrafluoroborate; In acetonitrile;

DOI:10.1002/ejoc.201200308

Reference yield: 95.0%

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

Guidance literature:

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

Reference yield: 85.0%

(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)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 2h; Inert atmosphere; Reflux;

DOI:10.1021/ol901416e

upstream raw materials:

diazomethane

6-(4-methoxy-trans-styryl)-pyran-2,4-dione

(4-Methoxy-2-oxo-2H-pyran-6-yl)methyltriphenylphosphonium Bromide

4-methoxy-benzaldehyde

Downstream raw materials:

4-methoxy-6-(p-methoxyphenethyl)-2H-pyran-2-one

(E)-6-(4-hydroxystyryl)-4-methoxy-2H-pyran-2-one

Refernces

• 1、 Chang, Bill C. H.,Dilrukshi Herath, H. M. P.,Garcia-Bustos, José,Gasser, Robin B.,Hofmann, Andreas,Jabbar, Abdul,Ma, Guangxu,Nguyen, Nghi,Sleebs, Brad E.,Taki, Aya C.,Wang, Tao. "Synthetic kavalactone analogues with increased potency and selective anthelmintic activity against larvae of haemonchus contortus in vitro". supporting information. . Retrieved 2020/04/30.
• 2、 -. "BONE METABOLISM IMPROVER". Paragraph 0055. . Retrieved 2018/09/26.