490-46-0
2-(3,4-dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene
CAS: 490-46-0
Molecular Formula: C15H14O6
490-46-0 - Names and Identifiers
| Name | 2-(3,4-dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene |
| Synonyms | EC L-Epicatechin (-)-epicatecho (-)-EPICATECHIN (-)-epicatechol (+)-EPICATECHIN 3,3',4',5,7-PENTAHYROXYFLAVONE 3,3',4',5,7-PENTAHYDROXYFLAVAN 3,3',4',5,7-PENTAHYDROXY-FLAVANE 2-(3,4-dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene (2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-1(2H)-BENZOPYRAN-3,5,7-TRIOL |
| CAS | 490-46-0 |
| EINECS | 207-710-1 |
| InChI | InChI=1/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 |
| InChIKey | PFTAWBLQPZVEMU-UKRRQHHQSA-N |
490-46-0 - Physico-chemical Properties
| Molecular Formula | C15H14O6 |
| Molar Mass | 290.27 |
| Density | 1.593±0.06 g/cm3(Predicted) |
| Melting Point | 240℃ |
| Boling Point | 629.2 °C |
| Specific Rotation(α) | -55～-65゜(D/20°C)(c=1,CH3OH) |
| Water Solubility | Soluble in water or alcohol |
| Solubility | Soluble in hot methanol, DMSO and other solvents, insoluble in petroleum ether, chloroform. |
| Appearance | morphology neat |
| pKa | 9.54±0.10(Predicted) |
| Storage Condition | -20°C |
| MDL | MFCD00075648 |
| Physical and Chemical Properties | Chemical Properties Derived from Peeled Branches of Leguminosae Catechu [Acacia catechu (L.F.) Willd] |
| Use | Uses for content determination/identification/pharmacological experiments. Pharmacological Efficacy: prevention and treatment of cardiovascular disease, cancer prevention, antioxidant effect. |
490-46-0 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | KB3745000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29329990 |
490-46-0 - Upstream Downstream Industry
| Downstream Products | Procyanidin B1 |
490-46-0 - Nature
| specific rotation | -55~-65゜(D/20℃)(c=1,CH3OH) |
| Merck | 13,1912 |
| BRN | 92760 |
Last Update：2024-04-10 22:29:15
490-46-0 - Uses and synthesis methods
overview
golden buckwheat is the dry rhizome of polygonaceae plant golden buckwheat Fagopyrumdibotrys. it has the effects of clearing away heat and detoxification, expelling pus and removing blood stasis. it is clinically used for the treatment of lung carbuncle vomiting pus, lung heat wheezing cough, swelling and pain of milk moth. Studies have shown that epicatechin and protocatechuic acid are the main components of Fagopyrum buckwheat for antibacterial, anti-inflammatory and antitussive. The content of epicatechin in ethanol extract of golden buckwheat accounts for 65% ~ 70%, and epicatechin has become an important index for the determination of golden buckwheat content. In addition, epicatechin also has a preventive effect on cardiovascular and cerebrovascular diseases, and can prevent tumors and has an antioxidant effect [1].
epicatechin can inhibit the inflammatory response of RAW264.7 cells induced by LPS, and its anti-inflammatory effect is related to inhibiting the production of cell inflammatory factors NO,TNF-α,IL-1 and IL-6, down-regulating the expression of I NOS protein, and mediating the regulation of activated MARK signaling pathway p38,ERK1 /2 and JNK protein expression.
antioxidant activity study
To study the antioxidant activity of (-)-epicatechin active substances in Fagopyrum japonica. Superoxide anion radical scavenging experiments showed that its antioxidant rate reached 83.08%; hydroxyl radical scavenging experiments showed that the effect of the mass concentration of the active substance on the scavenging rate was very significant (P<0.01), and the scavenging rate reached 77.30% at a mass concentration of 0.350 mg/m L; reducing force measurement experiments showed that its reducing force reached the 48.02% of the same mass concentration of VC, and the effect of mass concentration on the reducing force was; the active substance content in ethanol extract reached 1.40 mg/m L, accounting for 2.52% of the dry matter mass of root tubers. Experiments have proved that the active substance of Fagopyrum (-)-epatechin has good antioxidant activity and can be used as a natural and efficient antioxidant.
ethanol extraction process
Through the single-factor test method, the F test and the comparison of the new repolarization difference method (SSR method), the approximate range of ethanol concentration, extraction temperature, solid-liquid ratio, and extraction time were determined successively; then through the four-factor three-level orthogonal test, the optimized extraction process was as follows: ethanol volume fraction 60%, extraction temperature 20 ℃, solid-liquid ratio (g/m L) 1 ∶ 18, extraction time 30 min. The average extraction rate of epicatechin active substances from Fagopyrum japonica (-) reached 2. 5%. The process is simple and reasonable, and can be applied to the pre-production of golden buckwheat (-) epicatechin monomer industrialization.
toxicology data
1. acute toxicity: mouse LD50:1gm/kg via abdominal cavity, no detailed description except lethal dose;
2. mutagenic data: sister chromatid exchangeTEST system: human lymphocytes, 500mg/L.
ecological data
this substance may be harmful to the environment, and special attention should be paid to water bodies.
Last Update：2024-04-09 21:01:54
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