13164-04-0

Usage

Uses

Used in Pharmaceutical Industry:
Chalepin is used as a potential therapeutic agent for its anti-inflammatory properties, helping to reduce inflammation and alleviate pain in various conditions.
Used in Oncology:
Chalepin is used as an anti-cancer agent, targeting cancer cells and inhibiting their growth, making it a promising candidate for cancer treatment.
Used in Microbiology:
Chalepin is used as an anti-microbial agent, effective against various microorganisms, and can be utilized in the development of new antibiotics.
Used in Cosmetics Industry:
Chalepin is used as an anti-oxidant, protecting the skin from oxidative stress and promoting overall skin health.
Used in Diabetes Management:
Chalepin is used as an anti-diabetic agent, helping to regulate blood sugar levels and manage diabetes-related complications.

InChI:InChI=1/C19H22O4/c1-6-18(2,3)13-8-11-7-12-9-16(19(4,5)21)22-14(12)10-15(11)23-17(13)20/h6-8,10,16,21H,1,9H2,2-5H3

Upstream product

• 77712-80-2 7-O-(1,1-dimethyl-2-propynyl)-8-iodo-2H-1-benzopyran-2-one 
• 1242260-99-6 4-benzyloxy-2-(3-methylbut-2-enyloxy)benzaldehyde 
• 1242261-00-2 C₂₇H₃₄O₅ 
• 1242261-01-3 7-benzyloxy-6-(3-methylbut-2-enyl)-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 52085-14-0 4-benzoxy-salicylaldehyde 
• 112699-35-1 8-iododemethylsuberosin acetate 
• 112723-61-2 6-(3',3'-dimethylallyl)-7-(3'',3''-dimethylallyloxy)-8-iodocoumarin 
• 112699-37-3 8-iododemethylsuberosin 
• 104311-20-8 7-(1',1'-dimethylallyloxy)-8-iodocoumarin 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 65763-00-0 7-hydroxy-8-iodocoumarin 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 21316-80-3 7-hydroxy-6-(3-methylbut-2-enyl)-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one 

Downstream Products

• 14882-94-1 (+/-)-rutamarin 

Relevant academic research and scientific papers

Improved total synthesis of racemic rutamarin

An improved, convenient and cost-effective process, using 2,4-dihydroxybenzaldehyde 2 as starting material for (±)-rutamarin 1, is described. The overall yield of 1 is 44% in eight steps, requiring no chromatographic purification. The Japan Institute of Heterocyclic Chemistry.

SYNTHESIS OF 3-(1',1'-DIMETHYLALLYL)COUMARINS: GRAVELLIFERONE, CHALEPIN AND RUTAMARIN

The 3-(1',1'-dimethylallyl)coumarins chalepin (2), rutamarin (3) and gravelliferone (4) have been synthesized from umbelliferon (7) via Claisen and Cope rearrangements of 3',3'-dimethylallyl ethers of 6-(3',3'-dimethylallyl)umbelliferon with and without an iodine atom as blocking group at C-8.

Synthesis of 3-(1,1-Dimethylallyl)xanthyletin, 3-(1,1-Dimethylallyl)-8-(3,3-dimethylallyl)xanthyletin, Gravelliferone and dl-Chalepin

The synthesis of title compounds has been achieved from the key intermediate 3-(1,1-dimethylallyl)-7-hydroxycoumarin (7) which, in turn, is obtained by triple Claisen rearrangement of 7-(3,3-dimethylallyl)oxycoumarin (2) using butyric anhydride as the trapping reagent.