Isorhamnetin supplier | CasNO.480-19-3

Name
Isorhamnetin
EINECS 207-545-5
CAS No. 480-19-3
Article Data68
CAS DataBase
Density 1.634 g/cm³
Solubility
Melting Point 307 °C
Formula C₁₆H₁₂O₇
Boiling Point 599.429 °C at 760 mmHg
Molecular Weight 316.267
Flash Point 227.827 °C
Transport Information
Appearance powder
Safety 22-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogen cation	A n/a B 63%
With acid hydrolysis

: 2,3-dihydroisorhamnetin

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With potassium pyrosulfite In ethanol at 100℃; for 5h;	55%

: 604-80-8, 3520-85-2, 24905-37-1, 53584-69-3, 62249-59-6, 107740-46-5, 145264-20-6
narcissin

A: 3615-41-6
L-Rhamnose

B: 50-99-7
D-glucose

C: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With sulfuric acid; water In ethanol	A n/a B n/a C 42%
With hydrogenchloride In water at 100℃;
With hydrogenchloride; water at 100℃; for 2h;

...Expand

: 65490-09-7
2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

: 121-33-5
vanillin

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
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%

: 117-39-5
quercetol

: 485-80-3, 15519-60-5, 60018-85-1, 60018-86-2, 79845-28-6
S-adenosyl-L-methionine

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogen cation In water

: 6743-96-0, 128331-43-1
Quercetin-7-O-monoglucoside

A: 2280-44-6
D-Glucose

B: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With hydrogenchloride for 4h;

: 117-39-5
quercetol

A: 1486-70-0
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on

B: 603-61-2
tamarixetin

C: 529-51-1
5-O-methylquercetin

D: 480-19-3
isorhamnetin

E: 90-19-7
rhamnetin

Conditions

Conditions	Yield
With O-methyl transferase from cell-free extract of Citrus mitis; <(14)CH3>-S-adenosyl-L-methionine; 2-hydroxyethanethiol In water; dimethyl sulfoxide at 35℃; for 0.5h; Product distribution; pH 7.5 buffer;

...Expand

: 604-80-8, 3520-85-2, 24905-37-1, 53584-69-3, 62249-59-6, 145264-20-6, 107740-46-5
quercetin 3'-O-methyl ether 3-O-α-L-rhamnopyranosyl-(1'''→6")-β-D-galactopyranoside

A: 10257-28-0
D-Galactose

B: 73-34-7
L-rhamnose

C: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With oxonium Product distribution;

...Expand

: 107603-09-8, 119945-81-2, 142784-28-9
3-<6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl>oxy-5-hydroxy-7-<β-L-mannopyranosyl>oxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzo-pyran-4-one

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With sulfuric acid at 90℃; for 0.5h;	11 mg

: isorhamnetin 3-O-rutinoside-4'-O-rhamnoside

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With hydrogenchloride In methanol

: 153-18-4, 18341-98-5, 36535-79-2, 56587-62-3, 77133-40-5, 52525-35-6
rutin

A: 10257-28-0
D-Galactose

B: 30738-01-3, 30912-14-2, 36465-64-2, 41546-43-4, 41546-44-5, 41546-45-6, 41546-46-7, 41546-47-8, 41546-48-9, 41546-49-0, 41546-50-3, 63865-04-3, 639-97-4, 20230-73-3
D-apiose

C: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With sulfuric acid In water for 0.5h; Heating;

...Expand

: 65982-77-6
2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone

anhydride of/the/ O-benzoyl-vanillic acid: anhydride of/the/ O-benzoyl-vanillic acid

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With sodium-<4-benzoyloxy-3-methoxy benzoate> at 180 - 185℃; Kochen des Reaktionsprodukts mit waessrig-alkoholischer Kalilauge;

persicarin: persicarin

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With hydrogenchloride

: isorhamnetin 3-O-(6''-E-p-coumaroyl-β-D-glucopyranoside)-7-O-β-D-glucopyranoside

A: 7400-08-0
p-Coumaric Acid

B: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With hydrogenchloride at 100℃; for 1h;

: 6758-51-6
isorhamnetin 3,7-O-di-β-D-glucopyranoside

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With sulfuric acid In methanol for 3h; Heating;	220 mg

: 6743-92-6, 50306-07-5, 5041-82-7
isorhamnetin-3-O-glucoside

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
Acid hydrolysis;

: 604-80-8, 3520-85-2, 24905-37-1, 53584-69-3, 62249-59-6, 107740-46-5, 145264-20-6
narcissin

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
Acid hydrolysis;
With hydrogenchloride at 100℃; for 1h;

: 604-80-8, 3520-85-2, 24905-37-1, 53584-69-3, 62249-59-6, 107740-46-5, 145264-20-6
narcissin

A: 26184-96-3, 552-74-9, 47235-47-2, 56906-86-6, 56942-81-5, 59246-67-2, 68398-81-2, 68567-48-6, 68567-49-7, 75828-90-9
rutinose

B: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With McIlvaine buffer; flavonol-3-O-β-heterodisaccharide glycosidase at 30℃; for 0.25h; pH=5.0; Enzyme kinetics;

: 117-39-5
quercetol

AdoMet: AdoMet

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With DL-dithiothreitol; HCl buffer; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 1h; pH=7.5; Enzyme kinetics; Enzymatic reaction;
With DL-dithiothreitol; HCl buffer; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 1h; pH=7.5; Enzymatic reaction;

: 40554-92-5
3,7-bis(benzyloxy)-2-[4-(benzyloxy)-3-hydroxyphenyl]-5-hydroxy-4H-1-benzopyran-4-one

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / K2CO3 / dimethylformamide 2: 85 percent / H2 / 10 percent Pd(OH)2 / ethanol; tetrahydrofuran / 6 h View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 8 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 25 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 25 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.08 h / 0 °C / Inert atmosphere 1.2: 15 h / 20 °C / Inert atmosphere 2.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 4 h / 20 °C View Scheme

: 56681-66-4
3-methoxy-4-acetoxybenzoyl chloride

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; H2O 2: triethylamine / 160 °C / Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge View Scheme

: 108-73-6
3,5-dihydroxyphenol

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; hydrogen chloride / Kochen des Reaktionsprodukts mit Alkohol 2: sodium salt of/the/ O-benzoyl-vanillic acid / 180 - 185 °C / Kochen des Reaktionsprodukts mit waessrig-alkoholischer Kalilauge View Scheme

: isorhamnetin 3-O-[-α-L-rhamnopyranosyl-(1->3)]-β-D-glucopyranoside

: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With hydrogenchloride; water In methanol for 4h; Reflux;

: 128331-43-1, 6743-96-0
isorhamnetin 7-O-β-D-glucopyranoside

A: 50-99-7
D-glucose

B: 480-19-3
isorhamnetin

Conditions

Conditions	Yield
With water Acidic conditions;

: 2956-16-3
uridine 5'-diphospho-D-galactose

: 480-19-3
isorhamnetin

: 5041-82-7, 6743-92-6, 50306-07-5
isorhamnetin 3-β-D-galactopyranoside

Conditions

Conditions	Yield
With 3-O-glycosyltransferase from Scutellaria baicalensis In dimethyl sulfoxide at 45℃; for 4h; pH=9; Enzymatic reaction; regiospecific reaction;	83%

: 480-19-3
isorhamnetin

: 528-04-1, 2616-63-9, 7277-98-7, 16465-33-1, 19014-00-7, 26234-54-8, 26575-17-7, 27963-82-2, 29217-44-5, 125639-14-7
uridine 5'-diphospho-N-acetylglucosamine

: isorhamnetin 3-O-N-acetylglucosamine

Conditions

Conditions	Yield
With 3-O-glycosyltransferase from Scutellaria baicalensis In dimethyl sulfoxide at 45℃; for 4h; pH=9; Enzymatic reaction; regiospecific reaction;	75%

: 480-19-3
isorhamnetin

: C16H9(2)H3O7

Conditions

Conditions	Yield
Stage #1: isorhamnetin With [D]-sodium hydroxide; platinum on activated charcoal; water-d2 at 130℃; for 9h; Inert atmosphere; Stage #2: With formic acid at 130℃; for 1h; Inert atmosphere;	75%

: 121-34-6
3-methoxy-4-hydroxybenzoic acid

: 480-19-3
isorhamnetin

: 108-73-6
3,5-dihydroxyphenol

: 133-89-1
UDP-glucose

: 480-19-3
isorhamnetin

: 6743-92-6, 50306-07-5, 5041-82-7
isorhamnetin-3-O-glucoside

Conditions

Conditions	Yield
With UDP glucose:flavonol glucosyltransferase enzyme preparation from Norway spruce needles In water for 0.75h; pH 8.0 bicine buffer;
With Populus deltoids Marsh PGT-3 at 37℃; for 0.5h; pH=7.5; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; regioselective reaction;

: 480-19-3
isorhamnetin

potash: potash

A: 108-73-6
3,5-dihydroxyphenol

B: 99-50-3
3,4-Dihydroxybenzoic acid

Conditions

Conditions	Yield
beim Schmelzen;

...Expand

: 10034-85-2
hydrogen iodide

: 480-19-3
isorhamnetin

: 117-39-5
quercetol

: 480-19-3
isorhamnetin

quercetin-3'-methyl ether-3.5.7.4'-tetraacetate: quercetin-3'-methyl ether-3.5.7.4'-tetraacetate

Conditions

Conditions	Yield
Acetylieren;

: 67-56-1
methanol

: 480-19-3
isorhamnetin

: 74-88-4
methyl iodide

quercetin-3.7.3'.4'-tetramethyl ether: quercetin-3.7.3'.4'-tetramethyl ether

...Expand

Isorhamnetin 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.

Product Name

Isorhamnetin

Synthetic route

Isorhamnetin Specification

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