30964-13-7 Usage
Description
Cynarin, also known as 1,3-Dicaffeoylquinic acid, is a polyphenol compound found in C. scolymus. It exhibits various biological activities, including anti-inflammatory, anti-melanogenic, and hypolipidemic effects. Its chemical structure allows it to interact with specific cellular targets, making it a potential candidate for pharmaceutical applications.
Uses
Used in Anti-Cancer Applications:
Cynarin is used as an inhibitor of P-glycoprotein-mediated transport in multidrug-resistant (MDR) cancer cells. This application helps overcome drug resistance in cancer therapy, enhancing the effectiveness of chemotherapeutic agents.
Used in Anti-Inflammatory Applications:
Cynarin is used as an anti-inflammatory agent in human coronary artery smooth muscle cells (HCASMCs). At a concentration of 10 μM, it decreases the expression and protein levels of inducible nitric oxide synthase (iNOS) when the cells are treated with a cytokine mixture.
Used in Anti-Melanogenic Applications:
Cynarin is used as an anti-melanogenic agent in B16F1 murine melanocytes. It reduces the protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF), inhibiting melanogenesis in B16F1 cells and decreasing tyrosinase activity in cell lysates when used at a concentration of 25 μM.
Used in Hypolipidemic Applications:
Cynarin is used as a hypolipidemic agent in sodium oleate-induced hyperlipidemic HepG2 cells. At concentrations of 20 and 40 μM, it reduces triglyceride levels compared to hyperlipidemic control cells, demonstrating its potential in managing hyperlipidemia and related health conditions.
Originator
Anghirol,Biofarm
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 of
chloroform are added in 4 to 5 portions. After acidifying by cautiously adding
iced hydrochloric acid (1:1), the solution is filtered and the collected
precipitate 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 access
of moisture while frequently stirring, the suspension is refluxed by boiling
slowly and gently until everything is dissolved except a small amount of
reddish, resinous materials that adhere to the bottom. Then solution is rapidly
decanted into another flask containing 1.0 g of phosphorus pentachloride and
the whole is refluxed gently for about 15-30 min, after which time evolution of
hydrochloric acid ceases. This solution is left to cool on air for 1-2 h, and
then, the obtained carbonylcaffeic acid chloride rapidly is filtered, washed with
low-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 under
vacuum and is heated to 120°C and then, slowly, to about 160°C, maintaining
this temperature for about 20-30 min. The molten mass is left to cool under
vacuum and then it is crushed in a mortar in the presence of water. This
material is washed with water several times. The residue is dissolved in
dioxin. 400 ml of cold, 3% barium hydroxide solution are added and cooled
with ice water and stirring vigorously in nitrogen atmosphere. The solution is
left standing insulated from contact with air for 20 h, whereupon the content
is rapidly acidified and concentrated in vacuum, on a water bath, to a volume
of about 80-100 ml. After cooling and standing, well protected from contact
with air, the brown material is filtered off and purified by crystallization from
50% acetic acid. 1,4-Dicaffeylquinic acid is obtained, melting point 226°-
228°C.
Therapeutic Function
Choleretic, Antihyperlipidemic
Check Digit Verification of cas no
The CAS Registry Mumber 30964-13-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,0,9,6 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 30964-13:
(7*3)+(6*0)+(5*9)+(4*6)+(3*4)+(2*1)+(1*3)=107
107 % 10 = 7
So 30964-13-7 is a valid CAS Registry Number.
