CAS No.500-62-9,YANGONIN Suppliers

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Basic Information

Molecular Structure:
CAS No.:	500-62-9
Name:	YANGONIN
Article Data:	19

Formula:	C₁₅H₁₄O₄
Molecular Weight:	258.274
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;
Density:	1.2 g/cm³
Melting Point:	155-157 °C
Boiling Point:	487.6 °C at 760 mmHg
Flash Point:	219.8 °C
Solubility:	Practically insol in water; sol in hot alcohol, glacial acetic acid, ethyl acetate, acetone; slightly sol in benzene, ether.
Appearance:	pale yellow powder
PSA:	48.67000
LogP:	2.82740

Synthetic route

: 1334928-11-8
4-methoxy-6-vinyl-2H-pyran-2-one

: 459-64-3
4-methoxybenzenediazonium tetrafluoroborate

: 500-62-9
yangonin

Conditions

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%

: 54108-46-2
(4-Methoxy-2-oxo-2H-pyran-6-yl)methyltriphenylphosphonium Bromide

: 123-11-5
4-methoxy-benzaldehyde

: 500-62-9
yangonin

Conditions

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

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

: 500-62-9
yangonin

Conditions

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

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

: 77-78-1
dimethyl sulfate

: 500-62-9
yangonin

Conditions

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

: 672-89-9
4-methoxy-6-methyl-2H-pyran-2-one

: 123-11-5
4-methoxy-benzaldehyde

: 500-62-9
yangonin

Conditions

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%

: 186581-53-3, 908094-01-9
diazomethane

: 501-57-5
6-(4-methoxy-trans-styryl)-pyran-2,4-dione

A: 101-35-9
2-methoxy-6-<2-(4-methoxyphenyl)ethenyl>pyran-4-one

B: 500-62-9
yangonin

Conditions

Conditions	Yield
With diethyl ether

...Expand

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

Conditions

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

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

Conditions

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: yangonin

Conditions

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

: 157287-08-6
(E)-tert-butyl 3,5-dioxo-7-(p-methoxyphenyl)hept-6-enoate

: 500-62-9
yangonin

Conditions

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

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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.