520-32-1

Basic information

• Product Name: Tricin
• Synonyms: TRICIN;3',5'-DIMETHOXY-4',5,7-TRIHYDROXYFLAVONE;5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one;5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one;Tricetin 3',5'-dimethyl ether;4',5,7-Trihydroxy-3',5'-dimethoxyflavone;5,7,4'-Trihydroxy-3',5'-dimethoxyflavone;5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one
• CAS NO: 520-32-1
• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.29
• Product Categories: Penta-substituted Flavones;API intermediates
• Mol File: 520-32-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 289～291℃
• Boiling Point: 598.5°C at 760mmHg
• Flash Point: 224°C
• Appearance: /
• Density: 1.483g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane (Slightly), DMSO (Slightly)
• PKA: 6.48±0.40(Predicted)
• CAS DataBase Reference: Tricin(CAS DataBase Reference)
• NIST Chemistry Reference: Tricin(520-32-1)
• EPA Substance Registry System: Tricin(520-32-1)

Safety Data

• Hazardous Substances Data: 520-32-1(Hazardous Substances Data)

Usage

Uses

Tricin is a type of flavanoid studied for its immunomodulatory effects.

Definition

ChEBI: The 3',5'-di-O-methyl ether of tricetin. Known commonly as tricin, it is a constituent of rice bran and has been found to potently inhibit colon cancer cell growth.

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

Synthetic route

3,5-dihydroxyphenol (108-73-6) + ethyl 2-cyanoacetate (105-56-6) + syringic aldehyde (134-96-3) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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%

1-[4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-3-(2,4,6-trihydroxy-phenyl)-propane-1,3-dione → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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 → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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%

5,7-dihydroxy-3',4',5'-trimethoxyflavone (18103-42-9) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

Conditions	Yield
With sulfuric acid

2-(4-benzyloxy-3,5-dimethoxy-phenyl)-5,7-dihydroxy-chromen-4-one (30778-02-0) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

Conditions	Yield
With hydrogenchloride; acetic acid

7,4'-dihydroxy-3',5'-dimethoxy-5-O-β-D-glucopyranosylflavone (32769-00-9) → D-glucose (50-99-7) + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

acetic acid (64-19-7) + 4-hydroxy-3,5-dimethoxy-benzoic acid 2-acetyl-3,5-dihydroxy-phenyl ester → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) + 3-acetyl-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-chromen-4-one

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

O-acetylsyringic acid (6318-20-3) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

O-acetylsyringic acid chloride (39657-47-1) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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 → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

2,4,6-trihydroxyacetophenone (480-66-0) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

methyl syringate (884-35-5) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

methyl 4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxybenzoate (134178-07-7) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

anhydride of 4-benzyloxy-3,5-dimethoxybenzoic acid (86978-66-7) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

tricin-4'-O-β-L-arabinoside (1253377-85-3) → L-arabinose (5328-37-0) + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

Conditions	Yield
With hydrogenchloride; water

C35H58O8Si3 → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-ethan-1-one (108956-90-7) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

tricin 7-O-β-glucopyranoside-2''-sulphate sodium salt (1392102-95-2) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

1-(2-Hydroxy-4,6-bis(methoxymethyl)phenyl)ethanone + O-acetylsyringic acid chloride (39657-47-1) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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 → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

tricetin (520-31-0) + S-adenosyl-L-methionine (485-80-3, 15519-60-5, 60018-85-1, 60018-86-2, 79845-28-6) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

tricin-7-β-D-glucopyranoside (32769-01-0) → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

7-O-[β-D-glucuronopyranosyl(1->2)-O-β-D-glucuronopyranoside]tricin → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

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

5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) + Epalrestat (82158-86-9, 82159-09-9, 124782-63-4, 124782-64-5) → 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	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h;	72%

3-thienyl iodide (10486-61-0) + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → C21H16O7S

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

5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) + acetic anhydride (108-24-7) → triacetyl tricin

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

5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → tricin 7-sulphate + tricin 4'-sulphate

Conditions	Yield
With aminosulfonic acid

C20H22N2O6 (191425-55-5) + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-(Phe-OtBu)-tricin (1270004-51-7)

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

C20H22N2O6 (191425-55-5) + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-Phe-tricin (1270004-59-5)

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

C19H26N2O8 (438246-17-4) + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-[Asp(OtBu)-OtBu]-tricin (1270004-52-8)

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

C19H26N2O8 (438246-17-4) + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-Asp-tricin (1270004-60-8)

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 + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-(Ala-OtBu)-tricin (1270004-49-3)

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

tert-butyl [(4-nitrophenoxy)carbonyl]-L-valinate + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-(Val-OtBu)-tricin (1270004-50-6)

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

tert-butyl [(4-nitrophenoxy)carbonyl]-L-valinate + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-Val-tricin (1270004-56-2)

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 + 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-(Gly-OtBu)-tricin (1270004-48-2)

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

5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1) → 4'-O-CO-Gly-tricin (1270004-54-0)

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

Upstream product

• 86978-66-7 anhydride of 4-benzyloxy-3,5-dimethoxybenzoic acid 
• 1253377-85-3 tricin-4'-O-β-L-arabinoside 
• 32769-01-0 tricin-7-β-D-glucopyranoside 
• 108-73-6 3,5-dihydroxyphenol 
• 105-56-6 ethyl 2-cyanoacetate 
• 134-96-3 syringic aldehyde 
• 39657-47-1 O-acetylsyringic acid chloride 
• 108956-90-7 1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-ethan-1-one 
• 134178-07-7 methyl 4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethoxybenzoate 
• 884-35-5 methyl syringate 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 6318-20-3 O-acetylsyringic acid 
• 64-19-7 acetic acid 
• 32769-00-9 7,4'-dihydroxy-3',5'-dimethoxy-5-O-β-D-glucopyranosylflavone 

Downstream Products

• 1270004-54-0 4'-O-CO-Gly-tricin 
• 1270004-55-1 4'-O-CO-Ala-tricin 
• 1270004-62-0 4'-O-CO-Ala-[Asp(OtBu)-OtBu]-tricin 
• 1270004-63-1 4'-O-CO-Ala-[Glu(OtBu)-OtBu]-tricin 
• 1270004-64-2 4'-O-CO-Ala-Asp-tricin 
• 1270004-47-1 4'-O-CO-Ala-Glu-tricin 
• 32769-00-9 7,4'-dihydroxy-3',5'-dimethoxy-5-O-β-D-glucopyranosylflavone 
• 32769-01-0 tricin-7-β-D-glucopyranoside 
• 1270004-52-8 4'-O-CO-[Asp(OtBu)-OtBu]-tricin 
• 1270004-51-7 4'-O-CO-(Phe-OtBu)-tricin 

Relevant articles and documents

A sulphated flavone glycoside from Livistona australis and its antioxidant and cytotoxic activity

A new flavone glycoside tricin 7-O - glucopyranoside-2-sulphate sodium salt along with 14 known flavonoid compounds were isolated and identified from the aqueous methanol extract of Livistona australis leaves. Their structures were established on the basis of extensive NMR (1H, 13C, HSQC and H-H COSY) and ESIMS data. Antioxidant and cytotoxicity properties of the methanol extract of the leaves as well as the new compound were investigated.

Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the in Vitro Cytotoxicity of Its Methylated Products

O-methylation of flavonoids is an important modification reaction that occurs in plants. O-methylation contributes to the structural diversity of flavonoids, which have several biological and pharmacological functions. In this study, an O-methyltransferase gene (CrOMT2) was isolated from the fruit peel of Citrus reticulata, which encoding a multifunctional O-methyltransferase and could effectively catalyze the methylation of 3’-, 5’-, and 7-OH of flavonoids with vicinal hydroxyl substitutions. Substrate preference assays indicated that this recombinant enzyme favored polymethoxylated flavones (PMF)-type substrates in vitro, thereby providing biochemical evidence for the potential role of the enzyme in plants. Additionally, the cytotoxicity of the methylated products from the enzymatic catalytic reaction was evaluated in vitro using human gastric cell lines SGC-7901 and BGC-823. The results showed that the in vitro cytotoxicity of the flavonoids with the unsaturated C2-C3 bond was increased after being methylated at position 3’. These combined results provide biochemical insight regarding CrOMT2 in vitro and indicate the in vitro cytotoxicity of the products methylated by its catalytic reaction.

Synthesis method of 5,7,4'-trihydroxy-3',5'-dimethoxyflavone

The invention discloses a synthesis method of 5,7,4'-trihydroxy-3',5'-dimethoxyflavone (I), and belongs to the technical field of preparation methods of chemical medicinal intermediates. The synthesismethod comprises the following steps: with 1,3,5-trihydroxybenzene (II) and ethyl cyanoacetate as raw materials, performing a condensation reaction to obtain 2-(2-chloro-1-iminoethyl)benzene-1, 3, 5-triphenol (III), then hydrolyzing the (III) in dilute hydrochloric acid to obtain 2-chloro-1-(2,4,6-trihydroxyphenyl)ethanone (IV), and then cyclizing the IV with 3,5-dimethoxy-4-hydroxybenzaldehyde in the presence of alkali to obtain the 5,7,4'-trihydroxy-3',5'-dimethoxyflavone (I). The used raw materials are relatively cheap and easy to obtain, the method is easy and convenient to operate, the product yield is relatively high, and a relatively high industrialization value is achieved.