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480-19-3

Basic Information
CAS No.: 480-19-3
Name: Isorhamnetin
Article Data: 68
Cas Database
Molecular Structure:
Molecular Structure of 480-19-3 (Isorhamnetin)
Formula: C16H12O7
Molecular Weight: 316.267
Synonyms: 3-Methoxy-3,4,5,7-tetrahydroxyflavone;3,5,7-trihydroxy-2-(4-hydroxy-3-methoxy-phenyl)chromen-4-one;4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2- (4-hydroxy-3-methoxyphenyl)-;3-Methoxyquercetin;3-Methylquercetine;4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-;4H-1-Benzopyran-4-one, 2-(3-methoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-;3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyrone;Flavone, 3-methoxy-3,4,5,7-tetrahydroxy-;C.I. 75680;4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)- (9CI);3-Methylquercetin;Flavonoid;3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one;
EINECS: 207-545-5
Density: 1.634 g/cm3
Melting Point: 307 °C
Boiling Point: 599.429 °C at 760 mmHg
Flash Point: 227.827 °C
Solubility: N/A
Appearance: powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-36-26
Transport Information: N/A
PSA: 120.36000
LogP: 2.29100
Synthetic route
25515-47-3

4.2'.4'.6'-tetrahydroxy-3-methoxy-trans-chalcone

480-19-3

isorhamnetin

Conditions
ConditionsYield
With potassium hydrogensulfate; sodium hydrogencarbonate; sodium carbonate In dichloromethane; water; acetone at 20℃; for 42h; pH=9;96.7%

3,7-bis(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxy-4H-chromen-4-one

480-19-3

isorhamnetin

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 4h;92%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol at 25℃; for 8h;90%
With palladium 10% on activated carbon; hydrogen In ethanol at 25℃;90%
With hydrogen; palladium dihydroxide In tetrahydrofuran; ethanol for 6h;85%
78386-02-4

7-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)- 3,5-dihydroxy-4H-chromen-4-one

480-19-3

isorhamnetin

Conditions
ConditionsYield
With 20% palladium hydroxide-activated charcoal In ethanol; cyclohexene for 1h; Inert atmosphere; Reflux;92%
With 10% palladium on activated carbon; hydrogen In ethanol at 20℃; for 5h;90%
6743-92-6, 50306-07-5, 5041-82-7

isorhamnetin-3-O-glucoside

A

2280-44-6

D-Glucose

B

480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogen cationA n/a
B 63%
With acid hydrolysis

2,3-dihydroisorhamnetin

480-19-3

isorhamnetin

Conditions
ConditionsYield
With potassium pyrosulfite In ethanol at 100℃; for 5h;55%
Conditions
ConditionsYield
With sulfuric acid; water In ethanolA n/a
B n/a
C 42%
With hydrogenchloride In water at 100℃;
With hydrogenchloride; water at 100℃; for 2h;
65490-09-7

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

121-33-5

vanillin

480-19-3

isorhamnetin

Conditions
ConditionsYield
Stage #1: 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone; vanillin With pyrrolidine; oxygen In water under 760.051 Torr;
Stage #2: With hydrogenchloride In methanol; water
41%
Conditions
ConditionsYield
With sodium azide; T133M and Y326R mutant of isoeugenol phenylpropanoid O-methyltransferase from Clarkia breweri In aq. buffer at 30℃; for 240h; pH=7.5; Reagent/catalyst; Enzymatic reaction; regioselective reaction;6.8%
With DL-dithiothreitol; recombinant Plagiochasma appendiculatum flavone 6-O-methyltransferase; magnesium chloride In aq. buffer at 37℃; for 0.5h; pH=7.5; Enzymatic reaction;
With Citrus reticulata O-methyltransferase gene-pET32a recombinant In aq. buffer at 37℃; for 2h; pH=8; Kinetics; Enzymatic reaction;
65982-77-6

2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone

4-acetoxy-3-methoxy-benzoic acid-anhydride

480-19-3

isorhamnetin

Conditions
ConditionsYield
With triethylamine at 160℃; Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge;
103839-19-6, 38836-51-0

3,5,7,4′-tetrahydroxy-8,3′-dimethoxyflavone-3-O-β-D-glucopyranoside

480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogen cation In water
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Specification

The Isorhamnetin, with the CAS registry number 480-19-3, is also known as 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one. It belongs to the product categories of Penta-substituted Flavones; Flavanols; Aromatics; Heterocycles; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals. Its EINECS registry number is 207-545-5. This chemical's molecular formula is C16H12O7 and molecular weight is 316.26. What's more, both its IUPAC name and systematic name are the same which is called 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one. It should be stored in a cool, dry and well-ventilated place. Isorhamnetin is an O-methylated flavonol, a type of chemical compound. It can be found in Tagetes lucida, a psychedelic plant from Mexico and Central America.

Physical properties about Isorhamnetin are: (1)ACD/LogP: 2.787; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.71; (4)ACD/LogD (pH 7.4): 1.42; (5)ACD/BCF (pH 5.5): 64.87; (6)ACD/BCF (pH 7.4): 3.29; (7)ACD/KOC (pH 5.5): 656.29; (8)ACD/KOC (pH 7.4): 33.29; (9)#H bond acceptors: 7; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 116.45 Å2; (13)Index of Refraction: 1.741; (14)Molar Refractivity: 78.117 cm3; (15)Molar Volume: 193.545 cm3; (16)Polarizability: 30.968×10-24cm3; (17)Surface Tension: 88.309 dyne/cm; (18)Density: 1.634 g/cm3; (19)Flash Point: 227.827 °C; (20)Enthalpy of Vaporization: 92.531 kJ/mol; (21)Boiling Point: 599.429 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1c3c(O/C(=C1/O)c2ccc(O)c(OC)c2)cc(O)cc3O
(2) InChI: InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
(3) InChIKey: IZQSVPBOUDKVDZ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intravenous 11100mg/kg (11100mg/kg)   Drugs in Japan Vol. 6, Pg. 63, 1982.