Tricin
Basic information
- CAS
520-32-1- Standard SMILES
COc1cc(-c2cc(=O)c3c(O)cc(O)cc3o2)cc(OC)c1O- InChIKey
HRGUSFBJBOKSML-UHFFFAOYSA-N- Molecular formula
- C17H14O7
- Average molar mass
- 330.29 g/mol
- Monoisotopic mass
- 330.07395278
Overview
3',5'-di-O-methyltricetin is 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. It has a role as a metabolite and an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor. It is a member of 3'-methoxyflavones, a dimethoxyflavone and a trihydroxyflavone. It is functionally related to a tricetin. It is a conjugate acid of a 3',5'-di-O-methyltricetin(1-).
Names & identifiers
- Preferred name
- Tricin
- IUPAC
- 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one
- English name
- Tricin
- Molecular formula
- C17H14O7
- Molecular weight
- 330.29
Names & synonyms
Tricin520-32-15,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one5,7,4'-trihydroxy-3',5'-dimethoxyflavone3',5'-O-dimethyltricetinD51JZL38TQDTXSID201999655,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-oneNSC-294579RefChem:520625,7,4'-trihydroxy-3',5'-dimethoxy-flavoneDTXCID80122456
Show more names
TricincTRICIN(P)Tricin-RMNsc 294579Phelipeone3’,5’-O-DimethyltricetinTricetin 3',5'-dimethyl ether
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one3',5'-DIMETHOXY-4',5,7-TRIHYDROXYFLAVONEMFCD002105803',5'-di-O-methyltricetin5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)chromen-4-oneUNII-D51JZL38TQCHEBI:59979AKOS005606119
Database identifiers
- CAS
520-32-1- PubChem CID
- 5281702
- DTXSID
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 105 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 491
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Physicochemical properties
- Melting point
- 289 · 289~291℃
- Boiling point
- 598.5 · 598.5±50.0 °C(Predicted)
- Density
- 1.483 · 1.483±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Dichloromethane (Slightly), DMSO (Slightly)
- pka
- 6.48 · 6.48±0.40(Predicted)
- form
- Solid
- color
- Yellow to Dark Yellow
- Major Application
- food and beverages
- Cosmetics Ingredients Functions
- SKIN PROTECTINGSKIN CONDITIONING
- 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
- InChIKey
- HRGUSFBJBOKSML-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesTricin is a type of flavanoid studied for its immunomodulatory effects.
Preparation methods
PreparationA novel method for synthesizing Tricin. Phloroglucinol (2) and chloroacetonitrile were condensed in hydrochloric acid/ethyl acetate in the presence of zinc chloride to give 2-(2-chloro-1-iminoethyl)benzene-1,3,5-triol (3), which was then hydrolyzed directly in dilute hydrochloric acid without purification to give 2-chloro-1-(2,4,6-trihydroxyphenyl)ethyl ketone (4). The target compound was then cyclized with eugenol under ultrasonic treatment and in the presence of the phase-transfer catalyst tetrabutylammonium bromide (TBAB). This process uses inexpensive and readily available raw materials, has mild reaction conditions, is convenient to operate, and is green and efficient, with a total yield of 74.1%.
Upstream & downstream products
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