520-32-1
Tricin
CAS: 520-32-1
Molecular Formula: C17H14O7
520-32-1 - Names and Identifiers
| Name | Tricin |
| Synonyms | TRICIN Tricin Tricetin 3',5'-dimethyl ether 3',5'-DIMETHOXY-4',5,7-TRIHYDROXYFLAVONE 4',5,7-Trihydroxy-3',5'-dimethoxyflavone 5,7,4'-Trihydroxy-3',5'-dimethoxyflavone 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 |
| CAS | 520-32-1 |
520-32-1 - Physico-chemical Properties
| Molecular Formula | C17H14O7 |
| Molar Mass | 330.29 |
| Density | 1.483±0.06 g/cm3(Predicted) |
| Melting Point | 289～291℃ |
| Boling Point | 598.5±50.0 °C(Predicted) |
| Solubility | Dichloromethane (Slightly), DMSO (Slightly) |
| Appearance | Solid |
| Color | Yellow to Dark Yellow |
| pKa | 6.48±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Physical and Chemical Properties | Yellow crystal, soluble in methanol, ethanol, DMSO and other organic solvents, derived from alfalfa Medicago sativa. |
520-32-1 - References
| Overview | tricin, chemical name 5,7,4 '-trihydroxy-3',5 '-dimethoxyflavone, a kind of natural flavonoids, widely distributed in gramineae and Euphorbiaceae plants, has anti-inflammatory, antioxidant, antitumor, antiviral and immunomodulatory effects. In addition, alfalfa can help plants resist bacterial and fungal attack, and inhibit the growth of weeds, can be used as a herbicide. At present, the commercially available alfalfa is mostly extracted from plants, and the cost is high and the price is high. At present, the main synthetic routes of alfalfa pigment are as follows: (1) the phenolic hydroxyl group of 3, 5-dimethoxy-4-hydroxybenzoic acid methyl ester is protected by tert-butyldimethylchlorosilane (TBDMSCl), and then the hydroxyl group of bis (trimethylsilyl)-Condensation reaction with 2,4, 6-trihydroxyacetophenone in the presence of lithium amide (LiHMDS) at -78 °c and finally hydrolysis in acetic acid and sulfuric acid at 100 °c to give 1, the overall yield was 82%. |
| Application | alfalfa (tricin) flavonoids, can inhibit the small intestine peristalsis contraction, and has significant anti-allergic, antioxidant, anti-tumor and other biological activities. In the bath final concentration of 1 x 10-5g/mL, 2 x 10-5g/mL and 4 x 10-5g/mL, it can obviously inhibit the increase of the tension of the ileum of sensitized guinea pigs caused by Schultz-Dale reaction (P<0.01), which indicates that alfalfa has the effect of anti type I allergic reaction, furthermore, it was found that the final concentration of 2 × 10-5g/mL in the bath could significantly inhibit the increase of normal guinea pig ileum tension induced by histamine (P<0.05), the results indicate that alfalfa element has a certain antagonistic effect on the allergic medium histamine. The mechanism of inhibiting the release of allergic reaction mediators has not been experimentally verified, which may be through the inhibition of intracellular cyclic adenosine monophosphate phosphodiesterase, resulting in the increase of intracellular cyclic adenosine monophosphate (cAMP) concentration, prevents the transport of calcium ions into mast cells, thereby stabilizing the mast cell membrane and preventing the release of allergic reaction mediators. In addition, if the alfalfa as raw material processing food, can supplement the nutrition of food, maintain the human body diet. However, alfalfa contains more dietary fiber, and the addition of excessive amount will have a certain effect on the baking quality of baked food. Experiments show that alfalfa can be added in the bread, so that the protein content of bread greatly increased. Although the addition of alfalfa can reduce the baking quality of bread, However, it can be improved by adding an appropriate amount of bread improver and emulsifier, and the maximum amount of alfalfa in bread is 2%. |
| mechanism of action | alfalfa (tricin) is a kind of natural flavonoids, widely distributed in Gramineae, it has anti-inflammatory, antioxidant, anti-tumor, antiviral and immunomodulatory effects. In addition, alfalfa can help plants resist bacterial and fungal attack, and inhibit the growth of weeds, can be used as a herbicide. |
| preparation method | a new method for the synthesis of alfalfa. Condensation of phloroglucinol (2) with chloroacetonitrile in the presence of zinc chloride in hydrochloric acid/ethyl acetate gives 2-(2-chloro-1-iminoethyl) benzene -1,3, 5-triphenol (3) was directly hydrolyzed in dilute hydrochloric acid without purification to give 2-chloro-1-(2,4, 6-trihydroxyphenyl) ethanone (4). 4 the target compound was prepared by cyclization with syringal in the presence of ultrasonic wave and phase transfer catalyst tetrabutylammonium bromide (TBAB). The process is cheap and easy to obtain raw materials, mild reaction conditions, convenient operation, green and efficient, the total yield of 74.1% |
| uses | alfalfa element has the effects of scavenging free radicals, antioxidation, lowering blood lipid and preventing cardiovascular and cerebrovascular diseases. for content determination/identification/pharmacological experiments. |
Last Update：2024-04-09 21:32:20
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Tel: +86-18821248368
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View History
520-32-1
1213617-50-5
2-Bromo-4-chloro-5-iodotoluene
1,2,3,4-tetrahydro-6,7-diMethoxy-, ethyl ester
7-Bromoimidazo[1,2-a]pyridin-3-amine
832739-39-6
trans,trans-2,4-Undecadienal
5-(4-nitrophenyl)furan-2-carbaldehyde
20357-25-9
2-chloro-6-(thiophen-2-yl)-4-(trifluoromethyl)pyridine-3-carbonitrile
1213617-50-5
2-Bromo-4-chloro-5-iodotoluene
1,2,3,4-tetrahydro-6,7-diMethoxy-, ethyl ester
7-Bromoimidazo[1,2-a]pyridin-3-amine
832739-39-6
trans,trans-2,4-Undecadienal
5-(4-nitrophenyl)furan-2-carbaldehyde
20357-25-9
2-chloro-6-(thiophen-2-yl)-4-(trifluoromethyl)pyridine-3-carbonitrile