YANGONIN
- Iupac Name：4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
- CAS No.: 500-62-9
- Molecular Weight：258.273
- Modify Date.: 2023-02-09 15:11
- Introduction: 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.
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1. Names and Identifiers
- 1.1 Name
- YANGONIN
- 1.2 Synonyms
(E)-4-Methoxy-6-(4-methoxystyryl)-2H-pyran-2-one (E)-4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one 11-METHOXYYANGONIN 2H-Pyran-2-one, 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]- 2H-Pyran-2-one, 4-methoxy-6-[(Z)-2-(4-methoxyphenyl)ethenyl]- 2H-Pyran-2-one, 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-, (E)- 2H-PYRAN-2-ONE, 4-METHOXY-6-[2-(4-METHOXYPHENYL)ETHENYL]-, (Z)- 4-Méthoxy-6-[(E)-2-(4-méthoxyphényl)éthènyl]-2H-pyran-2-one 4-Methoxy-6-((E)-4-methoxystyryl)pyran-2-one 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 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one 4-Methoxy-6-[(Z)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one 4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one 4-Methoxy-6-[b-(p-anisyl)vinyl]-a-pyrone 5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic Acid d-Lactone 5-hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoicacidgamma-lacton 6-(p-Methoxystyryl)-4-methoxy-a-pyrone
- 1.3 CAS No.
- 500-62-9
- 1.4 CID
- 5281575
- 1.5 Molecular Formula
- C15H14O4 (isomer)
- 1.6 Inchi
- 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+
- 1.7 InChkey
- XLHIYUYCSMZCCC-VMPITWQZSA-N
- 1.8 Canonical Smiles
- COC1=CC=C(C=C1)C=CC2=CC(=CC(=O)O2)OC
- 1.9 Isomers Smiles
- COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=O)O2)OC
2. Properties
- 2.1 Density
- 1.2
- 2.1 Melting point
- 155-157oC
- 2.1 Boiling point
- 487.6 °C at 760 mmHg
- 2.1 Refractive index
- 1.577
- 2.1 Flash Point
- 219.8 °C
- 2.1 Precise Quality
- 258.08900
- 2.1 PSA
- 48.67000
- 2.1 logP
- 2.82740
- 2.1 Appearance
- pale yellow powder
- 2.2 Storage
- 2-8°C
- 2.3 Color/Form
- Powder
- 2.4 Physical
- Solid
- 2.5 Water Solubility
- Practically insol in water; sol in hot alcohol, glacial acetic acid, ethyl acetate, acetone; slightly sol in benzene, ether.
- 2.6 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 GHS Classification
- Signal: Warning
GHS Hazard Statements
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes
P264, P270, P301+P312, P330, and P501
- 3.2 Usage
- 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.
4. Safety and Handling
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 WGK Germany
- 3
- 4.1 Specification
-
The Yangonin, with the CAS registry number 500-62-9, has the systematic name of 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one. And the molecular formula of the chemical is C15H14O4.
The characteristics of this chemical are as followings: (1)ACD/LogP: 1.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.74; (4)ACD/LogD (pH 7.4): 1.74; (5)ACD/BCF (pH 5.5): 12.48; (6)ACD/BCF (pH 7.4): 12.48; (7)ACD/KOC (pH 5.5): 211.96; (8)ACD/KOC (pH 7.4): 211.96; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.577; (14)Molar Refractivity: 70.99 cm3; (15)Molar Volume: 213.9 cm3; (16)Polarizability: 28.14×10-24cm3; (17)Surface Tension: 45.1 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 219.8 °C; (20)Enthalpy of Vaporization: 75.35 kJ/mol; (21)Boiling Point: 487.6 °C at 760 mmHg; (22)Vapour Pressure: 1.18E-09 mmHg at 25°C.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C/1O\C(=CC(\OC)=C\1)\C=C\c2ccc(OC)cc2
(2)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+
(3)InChIKey: XLHIYUYCSMZCCC-VMPITWQZBG
The toxicity data is as follows:
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| mouse |
LD50 |
intraperitoneal |
> 1500mg/kg (1500mg/kg) |
|
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969. |
| mouse |
LD50 |
intravenous |
41mg/kg (41mg/kg) |
BEHAVIORAL: ANTICONVULSANT |
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969. |
| mouse |
LD50 |
oral |
> 1500mg/kg (1500mg/kg) |
|
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969. |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
500-62-9Total: 14 Synthesis Route
8. Other Information
- 8.0 BRN
- 230710
- 8.1 Uses
- 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.
- 8.2 体外研究
-
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.
- 8.3 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.
- 8.4 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.1 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.2 Yangonin blocks the activation of NF-κB by TNF-α.3 It also inhibits anchorage-dependent and independent growth of bladder cancer cell lines through induction of autophagic cell death (IC50s = 15-59 mg/mL).4
9. Computational chemical data
- Molecular Weight: 258.273g/mol
- Molecular Formula: C15H14O4
- Compound Is Canonicalized: True
- XLogP3-AA: 2.7
- Exact Mass: 258.08920892
- Monoisotopic Mass: 258.08920892
- Complexity: 412
- Rotatable Bond Count: 4
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 44.8
- Heavy Atom Count: 19
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 1
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwQAAAAAAAAAABAAAAGgAAAAAADASAmAIyDoAABACIAiDSCAACCAAgIAAIiAAGCMgMJiKEMRqCMCAkwBEIqQeAwAAOIAAAAAAAAABAAAAAAAAAAAAAAAAAAA==
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YANGONIN
- Purity:99%Packing: 200kg/bag FOB
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- Time: 2022/11/15
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Yangonin
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- Purity:99%Packing: 200kg/bag FOB
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- Time: 2020/11/02
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