147022-95-5

Basic information

• Product Name: 3'-O-Demethylarctigenin
• Synonyms: 3'-O-Demethylarctigenin;(3R,4R)-3-[(3,4-Dihydroxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl]dihydro-2(3H)-furanone
• CAS NO: 147022-95-5
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.38508
• Mol File: 147022-95-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'-O-Demethylarctigenin(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-O-Demethylarctigenin(147022-95-5)
• EPA Substance Registry System: 3'-O-Demethylarctigenin(147022-95-5)

Safety Data

• Hazardous Substances Data: 147022-95-5(Hazardous Substances Data)

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 108102-77-8 (R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one 
• 26687-82-1 Arctigenin 

Downstream Products

• 1426297-67-7 C₂₂H₂₆O₇ 
• 1426297-66-6 C₂₆H₃₄O₆ 
• 1426297-65-5 C₂₄H₃₀O₆ 
• 1426297-64-4 C₂₃H₂₈O₆ 
• 1426297-63-3 C₂₃H₂₈O₆ 
• 1426297-62-2 C₂₂H₂₆O₆ 
• 1426297-61-1 (3R,4R)-3-(4-benzyloxy-3-hydroxybenzyl)-4-(3,4-dimethoxybenzyl)dihydrofuran-2-one 
• 157072-28-1 4-O-methyl-3'-O-demethyl-(-)-secoisolariciresinol 

Relevant articles and documents

Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring

One of the arctigenin stereoisomers, (8R,8′R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8′R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8′R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8′R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8′R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8′R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.

(-)-Arctigenin as a lead compound for anticancer agent

(-)-Arctigenin, an important active constituent of the traditional Chinese herb Fructus Arctii, was found to exhibit various bioactivities, so it can be used as a good lead compound for further structure modification in order to find a safer and more potent medicine. (-)-Arctigenin derivatives 1-5 of (-)-arctingen were obtained by modifying with ammonolysis at the lactone ring and sulphonylation at C (6′) and C (6″) and O-demethylation at CH3O-C (3′), CH3O-C (3″) and CH3O-C (4″), and their anticancer bioactivities were examined. 2013