72944-19-5

Usage

Uses

Used in Pharmaceutical Industry:
ARTEPILLIN C is used as an anti-inflammatory agent for reducing inflammation and alleviating symptoms associated with inflammatory conditions.
ARTEPILLIN C is used as an antimicrobial agent for inhibiting the growth of harmful microorganisms and preventing infections.
ARTEPILLIN C is used as an antioxidant for neutralizing free radicals and protecting cells from oxidative damage.
ARTEPILLIN C is used as an antitumor agent for preventing the growth and spread of cancer cells and enhancing the effectiveness of conventional cancer treatments.
ARTEPILLIN C is used as an immunomodulatory agent for modulating the immune system and supporting overall wellness.

InChI:InChI=1/C19H24O3/c1-13(2)5-8-16-11-15(7-10-18(20)21)12-17(19(16)22)9-6-14(3)4/h5-7,10-12,22H,8-9H2,1-4H3,(H,20,21)/b10-7+

Upstream product

• 3943-97-3 methyl 4-hydroxycinnamate 
• 870-63-3 prenyl bromide 
• 67903-03-1 2,6-di(3-methyl-2-butenyl)benzene-1,4-diol 
• 205433-77-8 2-allyl-1-allyloxy-4-methoxy-benzene 
• 13391-35-0 allyl (4-methoxyphenyl) ether 
• 64047-87-6 4-methoxy-2,6-di(2-propenyl)phenol 
• 584-82-7 2-allyl-4-methoxyphenol 
• 150-76-5 4-methoxy-phenol 
• 1208233-12-8 tert-butyl (E)-3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]acrylate 
• 79-10-7 acrylic acid 
• 364358-95-2 4-iodo-2,6-bis(3-methyl-2-butenyl)-phenol 
• 107390-44-3 3-[4-acetoxy-3,5-bis(3-methyl-2-butenyl)phenyl]-(2E)-propenoic acid methyl ester 
• 540-38-5 p-Iodophenol 
• 72944-04-8 artepillin C methyl ester 

Downstream Products

• 1208233-08-2 artepillin C phenethyl ester 
• 107390-44-3 3-[4-acetoxy-3,5-bis(3-methyl-2-butenyl)phenyl]-(2E)-propenoic acid methyl ester 
• 107390-24-9 3,5-bis-<3',3'-dimethylallyl>-coumaric acid acetate 

Relevant academic research and scientific papers

Palladium-Catalyzed Directed para C?H Functionalization of Phenols

Various practical methods for the selective C?H functionalization of the ortho and recently also of the meta position of an arene have already been developed. Following our recent development of the directing-group-assisted para C?H functionalization of toluene derivatives, we herein report the first remote para C?H functionalization of phenol derivatives by using a recyclable silicon-containing biphenyl-based template. The effectiveness of this strategy was illustrated with different synthetic elaborations and by the synthesis of various phenol-based natural products.

New synthesis of artepillin C, a prenylated phenol, utilizing lipase-catalyzed regioselective deacetylation as the key step

We have synthesized artepillin C, a diprenylated p-hydroxycinnamate originally isolated from Brazilian propolis and exhibiting antioxidant and antitumor activities, from 2,6-diallylphenol. Replacement of the terminal vinyl with 2,2-dimethylvinyl group by olefin cross-metathesis and subsequent transformation yielded 2,6-diprenyl-1,4-hydroquinone diacetate. Candida antarctica lipase B-catalyzed deacetylation in 2-propanol regioselectively removed the less hindered acetyl group to give 2,6-diprenyl-1,4-hydroquinone 1-monoacetate. After triflation of the liberated 4-hydroxy group, a three-carbon side chain was introduced by palladium-mediated alkenylation with methyl acrylate. Final hydrolysis of the esters furnished artepillin C.

Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes

The effects of Brazilian green propolis ethanol extract on Cry j1-induced cys-leukotrienes and histamine release from peripheral leukocytes of patients with allergic rhinitis were investigated. One of the key mechanisms for the anti-allergic properties of the extract was revealed to be the suppression of cys-LTs release. Furthermore, a series of propolis components and their phenethyl esters were synthesized and evaluated as inhibitors of cys-LTs release. Artepillin C, baccharin, and kaempferide were the major active components of the ethanol extract. The inhibitory activity of artepillin C phenethyl ester was comparable to that of existing LT synthesis inhibitors. Crown Copyright

PHENOL DERIVATIVES, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF

Disclosed are an efficient, safe process for producing artepillin C and derivatives thereof by an organic synthesis. The process comprises a step of reacting a phenol derivative with an acrylate or acrylic acid.

First total synthesis of artepillin C established by o,o′-diprenylation of p-halophenols in water

We have demonstrated that prenylation of phalophenols was dependent on the solvent effect and succeeded in o,o′-diprenylation of p-halophenols in water. Following the Mizoroki-Heck coupling of the diprenyl-piodophenol 3c with methyl acrylate and then hydr