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520-36-5

Basic Information
CAS No.: 520-36-5
Name: Apigenin
Article Data: 132
Cas Database
Molecular Structure:
Molecular Structure of 520-36-5 (Apigenin)
Formula: C15H10O5
Molecular Weight: 270.241
Synonyms: C.I. Natural Yellow 1;Prestwick_719;Versulin;4,5, 7-Trihydroxyflavone;2446-tetrahydroxychalcone;Apigenol;4H-1-Benzopyran-4-one,5,7-dihydroxy-2- (4-hydroxyphenyl)-;4H-1-Benzopyran-4-one, 5, 7-dihydroxy-2- (4-hydroxyphenyl)-;ND-9076;5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one;4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-;Spigenin;5,7,4-Trihydroxyflavone;4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)- (9CI);4,5,7-Trihydroxyflavone;5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone;2-(p-Hydroxyphenyl)-5,7-dihydroxychromone;Flavone, 4,5,7-trihydroxy-;
EINECS: 208-292-3
Density: 1.548 g/cm3
Melting Point: 345-350 °C
Boiling Point: 555.5 °C at 760 mmHg
Flash Point: 217 °C
Solubility: DMSO: 27 mg/mL
Appearance: Pale Yellow Crystalline Solid
Hazard Symbols: IrritantXi
Risk Codes: R36/37/38
Safety: S26;S36
Transport Information: N/A
PSA: 90.90000
LogP: 2.57680
Synthetic route

2,4’,5,7-tetrahydroxyflavanone

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With hydrogenchloride In methanol; water100%
480-41-1

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With sulfuric acid; iodine In dimethyl sulfoxide at 100℃; for 1.5h;95%
With pyridine; iodine for 4h; Heating;93%
With pyridine; iodine at 95℃; for 5h;66%
578-74-5

apigenin 7-O-glucoside

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;95%
Acid hydrolysis;
Acidic conditions;
110865-03-7

2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one

123-08-0

4-hydroxy-benzaldehyde

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
Stage #1: 2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one; 4-hydroxy-benzaldehyde With sodium hydroxide In ethanol; water
Stage #2: With hydrogenchloride Further stages.;
92%
Stage #1: 4-hydroxy-benzaldehyde With potassium hydroxide In ethanol; water for 0.166667h; Inert atmosphere;
Stage #2: 2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one In ethanol; water at 60℃; for 4h;
90%
With potassium hydroxide In ethanol at 20 - 60℃; for 6h;83%
5631-70-9

4',5,7-trimethoxyflavone

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With pyridine hydrochloride at 180 - 190℃; for 6h; Inert atmosphere;90%
With pyridine hydrochloride at 180℃; for 6h; Inert atmosphere;90%
With boron tribromide In dichloromethane at 20℃; for 24h; Inert atmosphere;90%
Stage #1: 4',5,7-trimethoxyflavone With aluminum (III) chloride In toluene at 80 - 140℃;
Stage #2: With hydrogenchloride In water; toluene at 0℃; Reagent/catalyst; Solvent; Temperature; Time;
61.5%
With hydrogen iodide In acetic anhydride at 115 - 118℃; for 6h;10 g
480-41-1

naringenin

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With iodine In pyridine at 90℃; for 8h;86%
With flavone synthase I Product distribution;
With GLUTATHIONE; N-[tris(hydroxymethyl)methyl]glycine; flavone synthase II; NADPH; potassium hydroxide at 25℃; for 0.5h; pH=7.9; Enzymatic reaction;
With 2,3-dicyano-5,6-dichloro-p-benzoquinone
25515-46-2, 73692-50-9

2',4',6',4-tetrahydroxydihydrochalcone

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With oxygen at 20℃; under 760.051 Torr; for 0.866667h; Reagent/catalyst;77%

1-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-(2,4,6-trihydroxy-phenyl)-propane-1,3-dione

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With sulfuric acid In acetic acid at 95 - 100℃; for 1h;76%
108-73-6

3,5-dihydroxyphenol

77103-47-0

ethyl (4-hydroxybenzoyl)acetate

520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
for 0.0633333h; microwave irradiation;66%
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    Product Name: Apigenin Chemical formula: C15H10O5 Molecular weight: 270.24 CAS: 520-36-5 Melting point: 347 ~ 348 ℃ Appearance: light yellow powder Specification Apigenin 1.2%, 3%, 90%, 95%, 98% , 4:1 10:1 Detection method: HPLC Appearance:

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    Apigenin 520-36-5

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Specification

The Apigenin, with the CAS registry number 520-36-5,is also known as 4',5,7-Trihydroxyflavone; 5,7,4'-Trihydroxyflavone. It belongs to the product categories of Natural Plant Extract;Inhibitors;Protein Kinase;Signalling. This chemical's molecular formula is C15H10O5 and molecular weight is 270.24.Its EINECS number is 208-292-3. What's more,Its systematic name is Apigenin.It is a Pale Yellow Crystalline Solid .The Apigenin is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. When you use it ,wear suitable protective clothing. Apigenin is a potent inhibitor of CYP2C9, an enzyme responsible for the metabolism of many pharmaceutical drugs in the body. Apigenin is a flavone that is the aglycone of several glycosides.

Physical properties about Apigenin are:
(1)ACD/LogP:  2.12; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  2.07; (4)ACD/LogD (pH 7.4):  0.94; (5)ACD/BCF (pH 5.5):  21.33; (6)ACD/BCF (pH 7.4):  1.56; (7)ACD/KOC (pH 5.5):  299.53; (8)ACD/KOC (pH 7.4):  21.96; (9)#H bond acceptors:  5; (10)#H bond donors:  3; (11)#Freely Rotating Bonds:  4; (12)Index of Refraction:  1.732; (13)Molar Refractivity:  69.852 cm3; (14)Molar Volume:  174.563 cm3; (15)Surface Tension:  79.5999984741211 dyne/cm; (16)Density:  1.548 g/cm3; (17)Flash Point:  217.064 °C; (18)Enthalpy of Vaporization:  86.806 kJ/mol; (19)Boiling Point:  555.505 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C\1c3c(O/C(=C/1)c2ccc(O)cc2)cc(O)cc3O;
(2)Std. InChI:InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H;
(3)Std. InChIKey:KZNIFHPLKGYRTM-UHFFFAOYSA-N.