Introduction：Basic information about Cynarin CAS 30964-13-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Cynarin Basic information
| Product Name: | Cynarin |
| Synonyms: | 1,5-DICAFFEOYLQUINIC ACID;1,3-DICAFFEOYLQUINIC ACID;Dicaffeoylquinic Acid, 1,3-;Cynarin, 98%, from Lonicera japonica;(1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid;CYNARIN(ECHINACEA);CYNARIN(ARTICHOKE);CYNARIN |
| CAS: | 30964-13-7 |
| MF: | C25H24O12 |
| MW: | 516.45 |
| EINECS: | 214-655-7 |
| Product Categories: | chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract |
| Mol File: | 30964-13-7.mol |
|
Cynarin Chemical Properties
| Melting point | 225-227° |
| alpha | D25 -59° (c = 2 in methanol) |
| Boiling point | 819.9±65.0 °C(Predicted) |
| density | 1?+-.0.1 g/cm3(Predicted) |
| storage temp. | Sealed in dry,2-8°C |
| solubility | methanol: soluble5mg/mL, clear, light yellow to yellow |
| form | Solid |
| pka | 2.58±0.50(Predicted) |
| color | faint yellow to yellow |
| Stability: | Hygroscopic |
| InChIKey | YDDUMTOHNYZQPO-GCBRTHAASA-N |
| SMILES | [C@@]1(OC(=O)C=CC2=CC=C(O)C(O)=C2)(C(O)=O)C[C@@H](O)[C@H](O)[C@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)C1 |
| LogP | 1.640 (est) |
| CAS DataBase Reference | 30964-13-7(CAS DataBase Reference) |
Safety Information
| Safety Statements | 24/25 |
| WGK Germany | 3 |
| HS Code | 29182900 |
Cynarin Usage And Synthesis
| Description | 1,3-Dicaffeoylquinic acid is a polyphenol that has been found in C. scolymus. It decreases the expression and protein levels of inducible nitric oxide synthase (iNOS) when used at a concentration of 10 μM in human coronary artery smooth muscle cells (HCASMCs) treated with a cytokine mixture. 1,3-Dicaffeoylquinic acid decreases protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16F1 murine melanocytes. It inhibits melanogenesis in B16F1 cells and decreases tyrosinase activity in cell lysates when used at a concentration of 25 μM. 1,3-Dicaffeoylquinic acid (20 and 40 μM) reduces triglyceride levels in sodium oleate-induced hyperlipidemic HepG2 cells compared to hyperlipidemic control cells. |
| Chemical Properties | White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from artichoke leaves, artichoke, forest senecio herb, and honeysuckle. |
| Originator | Anghirol,Biofarm |
| Uses | Cynarin is used on MDR cells in anti-cancer therapy as an inhibitor of P-glycoprotein-mediated transport. |
| Definition | ChEBI: 1,3-dicaffeoylquinic acid is an alkyl caffeate ester obtained by the formal condensation of hydroxy groups at positions 1 and 3 of ()-quinic acid with two molecules of trans-caffeic acid. It has a role as a plant metabolite. It is a quinic acid and an alkyl caffeate ester. It is functionally related to a trans-caffeic acid and a (-)-quinic acid. It is a conjugate acid of a 1,3-dicaffeoylquinate. |
| Manufacturing Process | 18.0 g of caffeic acid, suspended in 500 ml of water, are dissolved by adding sodium bicarbonate and stirring. The solution is cooled to 2°-3°C and then,while stirring continuously, 20.0 g of phosgene dissolved in 200 ml ofchloroform are added in 4 to 5 portions. After acidifying by cautiously addingiced hydrochloric acid (1:1), the solution is filtered and the collectedprecipitate is washed with water. Upon crystallization from glacial acetic acid,the carbonylcaffeic acid thus obtained melts at 238°-240°C (dec.).
5.0 g of carbonylcaffeic acid are suspended in 70 ml of ligroin (b. p. 120°-140°C). After adding 6.0 g of phosphorus pentachloride and avoiding accessof moisture while frequently stirring, the suspension is refluxed by boilingslowly and gently until everything is dissolved except a small amount ofreddish, resinous materials that adhere to the bottom. Then solution is rapidlydecanted into another flask containing 1.0 g of phosphorus pentachloride andthe whole is refluxed gently for about 15-30 min, after which time evolution ofhydrochloric acid ceases. This solution is left to cool on air for 1-2 h, andthen, the obtained carbonylcaffeic acid chloride rapidly is filtered, washed withlow-boiling ligroin and dried under vacuum at room temperature for about 1-1.5 h. Melting point 118°-120°C.
5.0 g of carbonylcaffeic acid chloride are thoroughly mixed with 12.8 g of dry,powdered quinide in a flask immersed in an oil bath. The flask is put undervacuum and is heated to 120°C and then, slowly, to about 160°C, maintainingthis temperature for about 20-30 min. The molten mass is left to cool undervacuum and then it is crushed in a mortar in the presence of water. Thismaterial is washed with water several times. The residue is dissolved indioxin. 400 ml of cold, 3% barium hydroxide solution are added and cooledwith ice water and stirring vigorously in nitrogen atmosphere. The solution isleft standing insulated from contact with air for 20 h, whereupon the contentis rapidly acidified and concentrated in vacuum, on a water bath, to a volumeof about 80-100 ml. After cooling and standing, well protected from contactwith air, the brown material is filtered off and purified by crystallization from50% acetic acid. 1,4-Dicaffeylquinic acid is obtained, melting point 226°-228°C. |
| Therapeutic Function | Choleretic, Antihyperlipidemic |
| References | [1] YANKUN CHEN. Discovery of Potential Inhibitors of Squalene Synthase from Traditional Chinese Medicine Based on Virtual Screening and In Vitro Evaluation of Lipid-Lowering Effect.[J]. Molecules, 2018. DOI: 10.3390/molecules23051040
[2] NING XIA. Artichoke, cynarin and cyanidin downregulate the expression of inducible nitric oxide synthase in human coronary smooth muscle cells.[J]. Molecules, 2014, 19 3: 3654-3668. DOI: 10.3390/molecules19033654 |
Cynarin Preparation Products And Raw materials
| Raw materials | PETROLEUM ETHER-->Sodium bicarbonate-->Hydrochloric acid-->Phosphorus pentachloride-->Caffeic acid |
