Tricin supplier | CasNO.520-32-1

Name
Tricin
EINECS
CAS No. 520-32-1
Article Data13
CAS DataBase
Density 1.483g/cm³
Solubility
Melting Point 289～291℃
Formula C₁₇H₁₄O₇
Boiling Point 598.5°C at 760mmHg
Molecular Weight 330.294
Flash Point 224°C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Flavone,4',5,7-trihydroxy-3',5'-dimethoxy- (7CI,8CI);Tricin (6CI);4',5,7-Trihydroxy-3',5'-dimethoxyflavone;5,7,4'-Trihydroxy-3',5'-dimethoxyflavone;NSC 294579;
PSA 109.36000
LogP 2.59400

Synthetic route

: 108-73-6
3,5-dihydroxyphenol

: 105-56-6
ethyl 2-cyanoacetate

: 134-96-3
syringic aldehyde

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Stage #1: 3,5-dihydroxyphenol; ethyl 2-cyanoacetate With zinc(II) chloride In ethyl acetate for 0.5h; Sealed tube; Stage #2: With hydrogenchloride In water; ethyl acetate at 60℃; for 12h; Sealed tube; Stage #3: syringic aldehyde Temperature; Further stages;	95%

...Expand

: 1-[4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-3-(2,4,6-trihydroxy-phenyl)-propane-1,3-dione

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With sulfuric acid In acetic acid at 95 - 100℃; for 1h;	82%

: 4,6-bis(methoxymethyl)-2-(4-acetoxy-3,5-dimethoxybenzoyloxy)acetophenone

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Stage #1: 4,6-bis(methoxymethyl)-2-(4-acetoxy-3,5-dimethoxybenzoyloxy)acetophenone With potassium hydroxide In pyridine at 50℃; for 0.333333h; Stage #2: With acetic acid In pyridine; water for 0.5h; Stage #3: With hydrogenchloride In methanol Reflux;	65%

: 18103-42-9
5,7-dihydroxy-3',4',5'-trimethoxyflavone

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With sulfuric acid

: 30778-02-0
2-(4-benzyloxy-3,5-dimethoxy-phenyl)-5,7-dihydroxy-chromen-4-one

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid

: 32769-00-9
7,4'-dihydroxy-3',5'-dimethoxy-5-O-β-D-glucopyranosylflavone

A: 50-99-7
D-glucose

B: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With hydrogenchloride at 80℃; for 2.5h; Hydrolysis;

: 64-19-7
acetic acid

: 4-hydroxy-3,5-dimethoxy-benzoic acid 2-acetyl-3,5-dihydroxy-phenyl ester

A: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

B: 3-acetyl-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-chromen-4-one

Conditions

Conditions	Yield
With sulfuric acid Heating;	A 178 mg B 132 mg

...Expand

: 6318-20-3
O-acetylsyringic acid

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: oxalyl chloride / 3 h / Heating 2: pyridine / benzene / 18 h / 25 °C 3: NaH / dimethylsulfoxide / 1.5 h / 60 °C 4: 178 mg / H2SO4 / Heating View Scheme

: 39657-47-1
O-acetylsyringic acid chloride

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / benzene / 18 h / 25 °C 2: NaH / dimethylsulfoxide / 1.5 h / 60 °C 3: 178 mg / H2SO4 / Heating View Scheme

: 4-acetoxy-3,5-dimethoxy-benzoic acid 2-acetyl-3,5-dihydroxy-phenyl ester

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / dimethylsulfoxide / 1.5 h / 60 °C 2: 178 mg / H2SO4 / Heating View Scheme

: 480-66-0
2,4,6-trihydroxyacetophenone

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiHMDS / THF 1) 1 h, -78 deg C 2) 2 h, -10 deg C 3) 1 h, -78 deg C 4) 16 h, r.t. 2: 82 percent / 0.5percent H2SO4 / acetic acid / 1 h / 95 - 100 °C View Scheme
Multi-step reaction with 2 steps 1: sodium-<4-benzyloxy-3,5-dimethoxy benzoate> / 185 °C / anschliessend Erwaermen mit aethanol. Kalilauge und Erhitzen des Rektionsprodukts mit wss. Kalilauge 2: aqueous hydrochloric acid; acetic acid View Scheme
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran 2: lithium hexamethyldisilazane / tetrahydrofuran / 72 h / -78 - 20 °C 3: sulfuric acid / acetic acid / 100 °C View Scheme

: 884-35-5
methyl syringate

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / N,N-diisopropylethylamine / dimethylformamide 2: LiHMDS / THF 1) 1 h, -78 deg C 2) 2 h, -10 deg C 3) 1 h, -78 deg C 4) 16 h, r.t. 3: 82 percent / 0.5percent H2SO4 / acetic acid / 1 h / 95 - 100 °C View Scheme
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran 2: lithium hexamethyldisilazane / tetrahydrofuran / 72 h / -78 - 20 °C 3: sulfuric acid / acetic acid / 100 °C View Scheme

: 134178-07-7
methyl 4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxybenzoate

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiHMDS / THF 1) 1 h, -78 deg C 2) 2 h, -10 deg C 3) 1 h, -78 deg C 4) 16 h, r.t. 2: 82 percent / 0.5percent H2SO4 / acetic acid / 1 h / 95 - 100 °C View Scheme
Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane / tetrahydrofuran / 72 h / -78 - 20 °C 2: sulfuric acid / acetic acid / 100 °C View Scheme

: 86978-66-7
anhydride of 4-benzyloxy-3,5-dimethoxybenzoic acid

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium-<4-benzyloxy-3,5-dimethoxy benzoate> / 185 °C / anschliessend Erwaermen mit aethanol. Kalilauge und Erhitzen des Rektionsprodukts mit wss. Kalilauge 2: aqueous hydrochloric acid; acetic acid View Scheme

: 1253377-85-3
tricin-4'-O-β-L-arabinoside

A: 5328-37-0
L-arabinose

B: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With hydrogenchloride; water

: C35H58O8Si3

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With sulfuric acid In acetic acid at 100℃;	105 g

: 108956-90-7
1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-ethan-1-one

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane / tetrahydrofuran / 72 h / -78 - 20 °C 2: sulfuric acid / acetic acid / 100 °C View Scheme

: 1392102-95-2
tricin 7-O-β-glucopyranoside-2''-sulphate sodium salt

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With hydrogenchloride; water at 100℃; for 2h;

: 1-(2-Hydroxy-4,6-bis(methoxymethyl)phenyl)ethanone

: 39657-47-1
O-acetylsyringic acid chloride

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine / 20 °C 2.1: potassium hydroxide / pyridine / 0.33 h / 50 °C 2.2: 0.5 h 2.3: Reflux View Scheme

: C11H14O5

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 0.17 h / 0 °C 1.2: 0 °C 2.1: pyridine / 20 °C 3.1: potassium hydroxide / pyridine / 0.33 h / 50 °C 3.2: 0.5 h 3.3: Reflux View Scheme

: 520-31-0
tricetin

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

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With Citrus reticulata O-methyltransferase gene-pET32a recombinant In aq. buffer at 37℃; for 2h; pH=8; Kinetics; Enzymatic reaction;

: 32769-01-0
tricin-7-β-D-glucopyranoside

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 100℃; for 4h;

: 7-O-[β-D-glucuronopyranosyl(1->2)-O-β-D-glucuronopyranoside]tricin

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 100℃; for 4h;

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 82158-86-9, 82159-09-9, 124782-63-4, 124782-64-5
Epalrestat

: 5-Hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl-2-((Z)-5-((E)-2-methyl-3-phenylallylidene)-4-oxo-2- thioxothiazolidin-3-yl) acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h;	72%

: 10486-61-0
3-thienyl iodide

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: C21H16O7S

Conditions

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In dichloromethane at 0℃; for 60h; Inert atmosphere; Irradiation;	60%

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 108-24-7
acetic anhydride

: triacetyl tricin

Conditions

Conditions	Yield
With pyridine for 12h; Ambient temperature;	13.3 mg

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

A: tricin 7-sulphate

B: tricin 4'-sulphate

Conditions

Conditions	Yield
With aminosulfonic acid

: 191425-55-5
C20H22N2O6

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-51-7
4'-O-CO-(Phe-OtBu)-tricin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;

: 191425-55-5
C20H22N2O6

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-59-5
4'-O-CO-Phe-tricin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 12 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 0 - 20 °C View Scheme

: 438246-17-4
C19H26N2O8

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-52-8
4'-O-CO-[Asp(OtBu)-OtBu]-tricin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;

: 438246-17-4
C19H26N2O8

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-60-8
4'-O-CO-Asp-tricin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 12 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 0 - 20 °C View Scheme

: (S)-tert-butyl 2-(((4-Nitrophenoxy)carbonyl)amino)propanoate

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-49-3
4'-O-CO-(Ala-OtBu)-tricin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;

: tert-butyl [(4-nitrophenoxy)carbonyl]-L-valinate

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-50-6
4'-O-CO-(Val-OtBu)-tricin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;

: tert-butyl [(4-nitrophenoxy)carbonyl]-L-valinate

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-56-2
4'-O-CO-Val-tricin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 12 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 0 - 20 °C View Scheme

: [N-(tert-butyl-glycyl)-carbamoyl]-p-nitrophenol

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-48-2
4'-O-CO-(Gly-OtBu)-tricin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;

: 520-32-1
5,7,4'trihydroxy-3',5'-dimethoxyflavone

: 1270004-54-0
4'-O-CO-Gly-tricin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 12 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 0 - 20 °C View Scheme

Tricin Specification

The Tricin, with CAS registry number of 520-32-1, belongs to the following product categories: (1)Penta-substituted Flavones; (2)API intermediates. Its systematic name and its IUPAC name are the same, which is 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)chromen-4-one.

Physical properties about this chemical are: (1)ACD/LogP: 2.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.343; (4)ACD/LogD (pH 7.4): 1.162; (5)ACD/BCF (pH 5.5): 34.327; (6)ACD/BCF (pH 7.4): 2.259; (7)ACD/KOC (pH 5.5): 419.437; (8)ACD/KOC (pH 7.4): 27.602; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 105.45 Å²; (13)Index of Refraction: 1.671; (14)Molar Refractivity: 83.209 cm³; (15)Molar Volume: 222.567 cm³; (16)Polarizability: 32.987×10^-24cm³; (17)Surface Tension: 67.793 dyne/cm; (18)Enthalpy of Vaporization: 92.414 kJ/mol; (19)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: COc1cc(cc(c1O)OC)c2cc(=O)c3c(cc(cc3o2)O)O
(2)InChI: InChI=1/C17H14O7/c1-22-14-3-8(4-15(23-2)17(14)21)12-7-11(20)16-10(19)5-9(18)6-13(16)24-12/h3-7,18-19,21H,1-2H3
(3)InChIKey: HRGUSFBJBOKSML-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)17(14)21)12-7-11(20)16-10(19)5-9(18)6-13(16)24-12/h3-7,18-19,21H,1-2H3
(5)Std. InChIKey: HRGUSFBJBOKSML-UHFFFAOYSA-N

Product Name

Tricin

Synthetic route

Tricin Specification

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