Tricin

Base Information

• Chemical Name: Tricin
• CAS No.: 520-32-1
• Molecular Formula: C17H14O7
• Molecular Weight: 330.294
• Hs Code.: 2914509090
• Mol file: 520-32-1.mol

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;

Chemical Property of Tricin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 289～291℃
• Refractive Index: 1.671
• Boiling Point: 598.5°C at 760mmHg
• PKA: 6.48±0.40(Predicted)
• Flash Point: 224°C
• PSA: 109.36000
• Density: 1.483g/cm³
• LogP: 2.59400
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-5,6-dihydro-4H-chromen-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Tricin

There total 24 articles about Tricin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

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)

Guidance literature:

3,5-dihydroxyphenol; ethyl 2-cyanoacetate; With zinc(II) chloride; In ethyl acetate; for 0.5h; Sealed tube;

With hydrogenchloride; In water; ethyl acetate; at 60 ℃; for 12h; Sealed tube;

syringic aldehyde; Temperature; Further stages;

Reference yield: 82.0%

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)

Guidance literature:

With sulfuric acid; In acetic acid; at 95 - 100 ℃; for 1h;

DOI:10.1021/jo00016a015

Reference yield: 65.0%

4,6-bis(methoxymethyl)-2-(4-acetoxy-3,5-dimethoxybenzoyloxy)acetophenone → 5,7,4'trihydroxy-3',5'-dimethoxyflavone (520-32-1)

Guidance literature:

4,6-bis(methoxymethyl)-2-(4-acetoxy-3,5-dimethoxybenzoyloxy)acetophenone; With potassium hydroxide; In pyridine; at 50 ℃; for 0.333333h;

With acetic acid; In pyridine; water; for 0.5h;

With hydrogenchloride; In methanol; Reflux;

DOI:10.2174/1570178611999140206115633

upstream raw materials:

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

2-(4-benzyloxy-3,5-dimethoxy-phenyl)-5,7-dihydroxy-chromen-4-one

7,4'-dihydroxy-3',5'-dimethoxy-5-O-β-D-glucopyranosylflavone

acetic acid

Downstream raw materials:

4'-O-CO-Gly-tricin

4'-O-CO-Ala-tricin

4'-O-CO-Ala-[Asp(OtBu)-OtBu]-tricin

4'-O-CO-Ala-[Glu(OtBu)-OtBu]-tricin

Refernces

• 1、 Parveen, Mehtab,Khanam, Zakia,Ali, Akhtar,Ahmad, Syed Mohmud. "A novel antimicrobial flavonoidic glycoside from the leaves of Alstonia macrophylla Wall ex A. DC (Apocynaceae)". . p. 593 - 595. Retrieved 2010.
• 2、 Grignon-Dubois, Micheline,De Montaudouin, Xavier,Rezzonico, Bernadette. "Flavonoid pattern inheritance in the allopolyploid Spartina anglica – Comparison with the parental species S. maritima and S. alterniflora". . . Retrieved 2020/03/27.
• 3、 Pandurangan. "A new synthesis for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones by modified Baker-Venkataraman transformation". . p. 225 - 229. Retrieved 2014/05/20.