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529-44-2

Basic Information
CAS No.: 529-44-2
Name: Myricetin
Molecular Structure:
Molecular Structure of 529-44-2 (Myricetin)
Formula: C15H10O8
Molecular Weight: 318.24
Synonyms: Flavone,3,3',4',5,5',7-hexahydroxy- (8CI);3,3',4',5,5',7-Hexahydroxyflavone;3,5,7,3',4',5'-Hexahydroxyflavone;Cannabiscetin;4H-1-benzopyran-4-one, 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-;3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphényl)-4H-chromén-4-one;
EINECS: 208-463-2
Density: 1.912 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 747.6 °C at 760 mmHg
Flash Point: 285.9 °C
Solubility: slightly soluble in water
Appearance: brown-yellow to brown-green crystalline powder
Hazard Symbols:
Risk Codes:
Safety: 24/25
Transport Information:
PSA: 151.59000
LogP: 1.69360
Synthetic route
14585-04-7

5,7-dihydroxy-3,3',4',5'-tetramethoxyflavone

529-44-2

myricetin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 10 - 15℃; for 10h;95.2%
529-44-2

myricetin

Conditions
ConditionsYield
Acidic conditions;64%

Azamicroside

A

6014-42-2

L-rhamnose

B

529-44-2

myricetin

Conditions
ConditionsYield
With sulfuric acid for 0.0666667h; Heating;A n/a
B 45%
With sulfuric acid for 0.0666667h; Heating;A n/a
B 45%
27200-12-0

ampelopsin

529-44-2

myricetin

Conditions
ConditionsYield
Stage #1: ampelopsin With sodium hydroxide In water for 0.25h; Reflux;
Stage #2: With selenium(IV) oxide In water for 1.5h; Reagent/catalyst; Reflux;
42%
10034-85-2

hydrogen iodide

256486-48-3

2',6,6',8-tetrabromo-3,3',4',5,5',7-hexahydroxyflavone

529-44-2

myricetin

myricetin-3.3'.4'.5'-tetramethyl ether

myricetin-3.3'.4'.5'-tetramethyl ether

529-44-2

myricetin

Conditions
ConditionsYield
With hydrogen iodide; acetic anhydride
myricetin-5.7.3'.4'.5'-pentamethyl ether

myricetin-5.7.3'.4'.5'-pentamethyl ether

529-44-2

myricetin

Conditions
ConditionsYield
With hydrogen iodide; phenol
potato flowers of the variety "Rozovyi rannii"

potato flowers of the variety "Rozovyi rannii"

529-44-2

myricetin

Conditions
ConditionsYield
With hydrogenchloride; ethanol for 4h; Heating;

myricetin-3,5,3'-trimethyl ether

529-44-2

myricetin

Conditions
ConditionsYield
With hydrogen iodide; phenol at 145℃; for 0.5h;7 mg
17912-87-7

myricitrin

529-44-2

myricetin

Conditions
ConditionsYield
With naringinase In acetate buffer at 20℃; for 3h; pH=5.5; Enzymatic reaction;
17912-87-7

myricitrin

A

3615-41-6

L-Rhamnose

B

529-44-2

myricetin

Conditions
ConditionsYield
With hydrogenchloride; water for 0.25h; Heating;
1241909-29-4

myricetin-3-O-β-D-galactoside-3'-O-α-D-glucoside

A

2280-44-6

D-Glucose

B

10257-28-0

D-Galactose

C

529-44-2

myricetin

Conditions
ConditionsYield
With sulfuric acid In methanol at 90℃; for 2h;
1241909-30-7

myricetin-3-O-β-D-galactoside-3'-O-α-D-galactoside

A

10257-28-0

D-Galactose

B

529-44-2

myricetin

Conditions
ConditionsYield
With sulfuric acid In methanol at 90℃; for 2h;
100-53-8

phenylmethanethiol

proanthocyanidin

proanthocyanidin

A

220886-23-7

(epi)gallocatechin-3-O-gallate benzylthioether

B

529-44-2

myricetin

C

213007-61-5

(-)-epicatechin benzylthioether

D

220886-22-6

epigallocatechin-4-benzylthioether

G

(epi)catechin-3-O-gallate benzylthioether

Conditions
ConditionsYield
With hydrogenchloride In methanol at 60℃; for 2h;
15648-86-9, 19833-12-6

myricetin 3-O-β-D-glucopyranoside

A

50-99-7

D-glucose

B

529-44-2

myricetin

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 100℃; for 2h;
Acidic conditions;
1357272-88-8

myricetin 3-O-(2'',3''-digalloyl)-β-D-galactopyranoside

A

59-23-4

D-Galactose

B

149-91-7

3,4,5-trihydroxybenzoic acid

C

529-44-2

myricetin

Conditions
ConditionsYield
Stage #1: myricetin 3-O-(2'',3''-digalloyl)-β-D-galactopyranoside With sulfuric acid; water at 85℃; for 3h;
Stage #2: In water
557792-97-9

ampelopsin

529-44-2

myricetin

Conditions
ConditionsYield
In water at 100℃; for 12h;
480-18-2

taxifolin

A

99-50-3

3,4-Dihydroxybenzoic acid

B

83-30-7

acide 2,4,6-trihydroxybenzoique

C

C15H10O7

D

30048-34-1

2-(3',4'-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid

E

2'-hydroxytaxifolin

F

69098-01-7

2-oxo-2-(2,4,6-trihydroxyphenyl)acetic acid

G

529-44-2

myricetin

H

139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
With oxygen; potassium hydroxide In methanol

myricetin 3-O-β-4C1-galactopyranouronoide

529-44-2

myricetin

Conditions
ConditionsYield
With acetic acid In water at 100℃; for 0.5h;

myricetin 3-O-β-4C1-galactopyranouronoide

A

685-73-4

D-galacturonic acid

B

529-44-2

myricetin

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 2h;

myricetin 3-O-(2'',4''-di-O-acetyl)-α-L-rhamnopyranoside

A

3615-41-6

L-Rhamnose

B

529-44-2

myricetin

Conditions
ConditionsYield
Acidic conditions;
108-73-6

3,5-dihydroxyphenol

529-44-2

myricetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / ethyl acetate / 7 h / 20 °C
2: triethylamine / 6 h / 90 °C
3: boron tribromide / dichloromethane / 10 h / 10 - 15 °C
View Scheme
17912-87-7

myricitrin

A

7658-08-4

D-quionovose

B

529-44-2

myricetin

Conditions
ConditionsYield
With sulfuric acid In water for 4h;
529-44-2

myricetin

74-88-4

methyl iodide

14813-27-5

myricetin hexamethyl ether

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h;95%
With potassium carbonate In acetone for 14h; Heating;
529-44-2

myricetin

51-05-8

procaine hydrochloride

6,8-bis{p-[2-(diethylamino)ethoxycarbonyl]benzeneazo}-3,3',4',5,5',7-hexahydroxyflavone

Conditions
ConditionsYield
Stage #1: procaine hydrochloride With hydrogenchloride; sodium acetate; sodium nitrite In water Diazotization;
Stage #2: myricetin In ethanol; water at 25℃; Substitution;
95%
529-44-2

myricetin

121-57-3

4-aminobenzene sulfonic acid

sodium salt of 6,8-bis(p-sulfobenzeneazo)-3,3',4',5,5',7-hexahydroxyflavone

Conditions
ConditionsYield
Stage #1: 4-aminobenzene sulfonic acid With sodium hydroxide; sodium nitrite In water at 0℃; for 1h; Diazotization;
Stage #2: myricetin In ethanol; water at 25℃; for 1h; Substitution;
Stage #3: With sodium chloride In ethanol; water at 0℃; for 3h; Sodium salt formation;
95%
529-44-2

myricetin

phenylhydrazine acetate

phenylhydrazine acetate

4,4',7-tris(phenylhydrazono)-3,3',5,5'-tetrahydroxyflavone

Conditions
ConditionsYield
In ethanol; acetic acid at 90 - 95℃; for 5h; Condensation;93%
529-44-2

myricetin

3,3',4',5,5',7-hexahydroxy-α-hydroxychalcone

Conditions
ConditionsYield
With ammonium hydroxide In ethanol at 60℃; for 1.5h; Ring cleavage;86%
529-44-2

myricetin

108-24-7

acetic anhydride

14813-29-7

[3,5-diacetoxy-4-oxo-2-(3,4,5-triacetoxyphenyl)chromen-7-yl] acetate

Conditions
ConditionsYield
With sodium acetate at 80℃; for 6h;85%
With pyridine at 15℃; for 16h;61%
With pyridine at 15℃; for 12h;61%
72-14-0

Sulfathiazole

529-44-2

myricetin

6,8-bis[p-(1,3-thiazol-2-ylsulfamoyl)benzeneazo]-3,3',4',5,5',7-hexahydroxyflavone

Conditions
ConditionsYield
Stage #1: Sulfathiazole With hydrogenchloride; sodium acetate; sodium nitrite In water Diazotization;
Stage #2: myricetin In ethanol; water at 25℃; Substitution;
82%
57-68-1

sulfadimesine

529-44-2

myricetin

6,8-bis[p-(4,6-dimethylpyrimidinylsulfamoyl)benzeneazo]-3,3',4',5,5',7-hexahydroxyflavone

Conditions
ConditionsYield
Stage #1: sulfadimesine With hydrogenchloride; sodium acetate; sodium nitrite In water Diazotization;
Stage #2: myricetin In ethanol; water at 25℃; Substitution;
81%
106-31-0

butanoic acid anhydride

529-44-2

myricetin

3,5-bis(butanoyloxy)-4-oxo-2-[3,4,5-tris(butanoyloxy)phenyl]-4H-chromen-7-yl butanoate

Conditions
ConditionsYield
With pyridine at 20℃; for 12h; Inert atmosphere;79.79%
529-44-2

myricetin

141-75-3

butyryl chloride

3,5-bis(butanoyloxy)-4-oxo-2-[3,4,5-tris(butanoyloxy)phenyl]-4H-chromen-7-yl butanoate

Conditions
ConditionsYield
With pyridine for 12h; Inert atmosphere;79.79%
529-44-2

myricetin

256486-45-0

3,3',4',5,5',7-hexahydroxy-2',6,6',8-tetranitroflavone

Conditions
ConditionsYield
With nitric acid In acetic acid at 20℃; for 3h; Nitration;77%
529-44-2

myricetin

256486-48-3

2',6,6',8-tetrabromo-3,3',4',5,5',7-hexahydroxyflavone

Conditions
ConditionsYield
With bromine In acetic acid at 20℃; for 3h; Bromination;75%
With carbon disulfide; bromine at 100℃;
529-44-2

myricetin

63-74-1

sulfanilamide

6,8-bis(p-sulfamoylbenzeneazo)-3,3',4',5,5',7-hexahydroxyflavone

Conditions
ConditionsYield
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite In water Diazotization;
Stage #2: myricetin In ethanol; water at 23 - 25℃; Substitution;
73%
529-44-2

myricetin

100-01-6

4-nitro-aniline

6,8-bis(p-nitrobenzeneazo)-3,3',4',5,5',7-hexahydroxyflavone

Conditions
ConditionsYield
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Diazotization;
Stage #2: myricetin In ethanol; water at 25℃; Substitution;
70%
4349-62-6

2-benzyloxybenzoyl chloride

529-44-2

myricetin

C99H70O20

Conditions
ConditionsYield
Stage #1: 2-benzyloxybenzoyl chloride; myricetin In acetonitrile at 20℃; for 0.5h;
Stage #2: With dmap at 20℃; for 12h;
63.4%
529-44-2

myricetin

74-88-4

methyl iodide

190323-49-0

3-hydroxy-5,7-dimethoxy-2–(3,4,5-trimethoxyphenyl)-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;54.4%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 60h;
Stage #1: myricetin With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 48h;
Stage #1: myricetin With 2K(1+)*CO3(2-)*0.5H2O=K2CO3*0.5H2O In N,N-dimethyl-formamide at 20℃;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 48h;
Stage #1: myricetin With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 48h;
7491-74-9

2-oxo-1-pyrrolidine acetamide

529-44-2

myricetin

C15H10O8*C6H10N2O2

Conditions
ConditionsYield
In isopropyl alcohol at 20℃; for 312h;54%
3590-12-3

N,N-bis(2-p-tolylsulfonyloxyethyl)aniline

529-44-2

myricetin

4'-O-(2-N,N-hydroxy ethyl-phenyl)-ethyl myricetin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Williamson Ether Synthesis;52%
529-44-2

myricetin

8-bromomyricetin

Conditions
ConditionsYield
With 2,3-dibromo-3-phenylpropanoic acid; caesium carbonate In N,N-dimethyl-formamide at 40℃; for 16h; Inert atmosphere; regioselective reaction;49%
529-44-2

myricetin

100-39-0

benzyl bromide

C43H34O8

Conditions
ConditionsYield
Stage #1: myricetin With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #2: benzyl bromide at 70℃; for 12h;
46%
6315-52-2

1,2-bis-tosyloxyethane

529-44-2

myricetin

4'-O-(2-hydroxy)ethylmyricetin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Williamson Ether Synthesis;45%
With potassium carbonate In N,N-dimethyl-formamide at 100℃;262 mg
16695-22-0

N,N-bis(tosyloxyethyl)-p-toluenesulfonamide

529-44-2

myricetin

4'-O-(2-N,N-hydroxy ethyl-toluene-4-sulfonyl)-ethyl myricetin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Williamson Ether Synthesis;45%
With potassium carbonate In N,N-dimethyl-formamide at 110℃;402 g
117-80-6

2,3-Dichloro-1,4-naphthoquinone

529-44-2

myricetin

A

3,4-dihydroxy-1-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)naphtho[2,3-b]benzofuran-6,11-dione

B

4-hydroxy-3-((3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)-1-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)naphtho[2,3-b]benzofuran-6,11-dione

C

3-hydroxy-4-((3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)-1-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)naphtho[2,3-b]benzofuran-6,11-dione

Conditions
ConditionsYield
With pyridine at 85℃; for 24h;A 45%
B 18%
C 16%
529-44-2

myricetin

7460-82-4

diethylene glycol ditosylate

4'-O-[2-(2-hydroxyethyl)hydroxy]ethylmyricetin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Williamson Ether Synthesis;36%
With potassium carbonate In N,N-dimethyl-formamide at 110℃;236 mg
529-44-2

myricetin

A

16280-27-6

3,5,3',4',5'-pentahydroxy-7-methoxyflavone

B

16805-10-0

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

C

7,4'-di-O-methylmyricetin

D

5-hydroxy-3,7-dimethoxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one

Conditions
ConditionsYield
In methanol; diethyl ether at 20℃; for 1h;A 25%
B 31%
C 9%
D 6%
529-44-2

myricetin

123-62-6

propionic acid anhydride

[4-oxo-3,5-di(propanoyloxy)-2-[3,4,5-tri(propanoyloxy)phenyl]chromen-7-yl] propanoate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; Inert atmosphere;30%
With pyridine at 0 - 20℃; Inert atmosphere;30%
With pyridine at 0℃; Inert atmosphere;30%
With pyridine at 0 - 20℃; Inert atmosphere;30%
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    529-44-2

    Myricetin

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    Myricetin CAS 529-44-2

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    Myricetin

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Chemistry

Molecular Structure:

IUPAC Name:3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
Molecular Formula:C15H10O8
Molecular Weight:318.2351
H bond acceptors: 8
H bond donors: 6
Freely Rotating Bonds: 7
Polar Surface Area: 81.68 Å2
Molar Refractivity: 75.2 cm3
Molar Volume: 166.4 cm3
Surface Tension: 133 dyne/cm
Density: 1.912 g/cm3
Melting Point: >300°C (lit.)
Boiling Point: 747.6°C  at 760 mmHg
Flash Point: 285.9°C
Index of Refraction: 1.863
Form: crystalline
Merck: 13,6357
EINECS: 208-463-2
Product Categories: Flavanols; Nutritional Ingredients
InChI
InChI=1/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H
Smiles
c12c(c(c(O)c(o1)c1cc(c(O)c(c1)O)O)=O)c(cc(c2)O)O

Uses

  Myricetin (CAS NO.529-44-2) is widely used in the fields of medicine, food, health care products and cosmetics. Myricetin (CAS NO.529-44-2) is mainly used as a additive to treat and prevent arthritis, especially for pregnant or lactating women. Myricetin (CAS NO.529-44-2) is favorable to decrease the side effects caused by antibiotics.

Toxicity Data With Reference

1.    

 

    PYTCAS    Phytochemistry. An International Journal of Plant Biochemistry. 26 (1987),2231.
2.    

dnd-hmn-hla 400 µmol/L

    MUREAV    Mutation Research. 390 (1997),141.
3.    

dni-hmn-hla 12500 µg/L

    PYTCAS    Phytochemistry. An International Journal of Plant Biochemistry. 27 (1988),1017. EXPEAM    Experientia. 44 (1988),882.

Safety Profile

Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Safety Statements:24/25
24/25:Avoid contact with skin and eyes
RTECS: LK8646000
F: 10
WGK Germany: 3

Specification

 Myricetin , with CAS number of 529-44-2, can be called 3,3’,4’,5,5’,7-hexahydroxy-flavon ; 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4h-1-benzopyran-4-on ; Cannabiscetin ; 3,3',4',5,5',7-hexahydroxyflavone ; 3',4',5',3,5,7-hexahydroxyflavone ; 3,5,7,3',4',5'-hexahydroxyflavone ; Myricetin ; Myricetol . Myricetin (CAS NO.529-44-2) is a compoud that belongs to flavonols. It is incompatibilities with strong oxidizing agents. It emits carbon monoxide and carbon dioxide when it is decomposed. Myricetin (CAS NO.529-44-2) belongs to flavonols. Myricetin (CAS NO.529-44-2) exists as a brown-yellow to brown-green crystalline powder, soluble in methanol, ethanol, acetone, ethyl acetate, slightly soluble in water, insoluble in chloroform, petroleum ether. Myricetin (CAS NO.529-44-2) is easily turns green in the air.