CAS 500-62-9|Yangonin

Introduction：Basic information about CAS 500-62-9|Yangonin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Yangonin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles15
8. Synonyms

Common Name	Yangonin
CAS Number	500-62-9	Molecular Weight	258.269
Density	1.2±0.1 g/cm3	Boiling Point	487.6±45.0 °C at 760 mmHg
Molecular Formula	C₁₅H₁₄O₄	Melting Point	155-157ºC
MSDS	ChineseUSA	Flash Point	219.7±28.8 °C

Names

Name	yangonin
Synonym	More Synonyms

Yangonin BiologicalActivity

Description	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 ReceptorResearch Areas >>Inflammation/ImmunologyNatural 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

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ1225200

CHEMICAL NAME :: 2H-Pyran-2-one, 4-methoxy-6-(p-methoxystyryl)-

CAS REGISTRY NUMBER :: 500-62-9

LAST UPDATED :: 199109

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C15-H14-O4

MOLECULAR WEIGHT :: 258.29

WISWESSER LINE NOTATION :: T6OVJ DO1 F1U1R DO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 41 mg/kg

TOXIC EFFECTS :: Behavioral - anticonvulsant

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

Safety Information

RIDADR	NONH for all modes of transport
HS Code	2932999099

Customs

HS Code	2932999099
Summary	2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles15

Fatal kavalactone intoxication by suicidal intravenous injection.

Forensic Sci. Int. 249 , e7-11, (2015)

Kavalactones are a group of compounds found in kava, a beverage or extract prepared from the rhizome of the kava plant (Piper methysticum). Traditionally kava extracts have been used for their anxioly...

Interaction of various Piper methysticum cultivars with CNS receptors in vitro.

Planta Med. 67(4) , 306-11, (2001)

Methanolic leaf and root extracts of the Hawaiian kava (Piper methysticum Forst.) cultivars, Mahakea, Nene, Purple Moi and PNG, were tested on binding affinities to CNS receptors including GABAA (GABA...

Kavalactones fail to inhibit alcohol dehydrogenase in vitro.

Phytomedicine 13(3) , 192-5, (2006)

In recent years, Kava kava (Piper methysticum, Forst. f., Piperaceae), a folkloric beverage and popular herbal remedy, has been implicated in a number of liver failure cases. Many hypotheses as to the...

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

2H-Pyran-2-one, 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-, (E)-

2H-Pyran-2-one, 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-

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

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