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520-32-1

520-32-1 Structure

520-32-1 Structure
IdentificationBack Directory
[Name]

Tricin
[CAS]

520-32-1
[Synonyms]

TRICIN
Tricinc
TRICIN(P)
Phelipeone
Nsc 294579
3',5'-di-O-methyltricetin
Tricetin 3',5'-dimethyl ether
4',5,7-Trihydroxy-3',5'-dimethoxyflavone
5,7,4'-Trihydroxy-3',5'-dimethoxyflavone
3',5'-DIMETHOXY-4',5,7-TRIHYDROXYFLAVONE
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one,5,7-dihydroxy-2-(4-hydroxy-3,5-diMethoxyphenyl)-
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-5,6-dihydro-4H-chromen-4-one
[Molecular Formula]

C17H14O7
[MDL Number]

MFCD00210580
[MOL File]

520-32-1.mol
[Molecular Weight]

330.29
Questions And AnswerBack Directory
[Preparation]

A 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%.
Chemical PropertiesBack Directory
[Melting point ]

289~291℃
[Boiling point ]

598.5±50.0 °C(Predicted)
[density ]

1.483±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[solubility ]

Dichloromethane (Slightly), DMSO (Slightly)
[form ]

Solid
[pka]

6.48±0.40(Predicted)
[color ]

Yellow to Dark Yellow
[Major Application]

food and beverages
[Cosmetics Ingredients Functions]

SKIN PROTECTING
SKIN 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
[SMILES]

C1(C2=CC(OC)=C(O)C(OC)=C2)OC2=CC(O)=CC(O)=C2C(=O)C=1
Safety DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Chemical Properties]

Yellow crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the whole herb of Medicago sativa.
[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.
[in vivo]

Tricin (50-250 ppm diet; 15 weeks) significantly lowers the numbers of adenocarcinomas and total tumors in mice[5].

[target]

TLR | p38MAPK | JNK | NF-kB | Phospholipase (e.g. PLA) | Tyrosinase | COX | JAK | STAT | Antifection
[storage]

4°C, protect from light
Spectrum DetailBack Directory
[Spectrum Detail]

Tricin(520-32-1)1HNMR
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