29388-33-8

Basic information

• Product Name: Phenol,4,4'-[[(3R,4R)-tetrahydro-3,4-furandiyl]bis(methylene)]bis[2-methoxy-
• Synonyms: Phenol,4,4'-[(tetrahydro-3,4-furandiyl)bis(methylene)]bis[2-methoxy-, (3R-trans)-; p-Cresol,a,a'-(tetrahydro-3,4-furandiyl)bis[2-methoxy-, (-)-(8CI); (-)-Anhydrosecoisolariciresinol; Ansecoisolariciresinol; Shonanin
• CAS NO: 29388-33-8
• Molecular Formula: C20H24 O5
• Molecular Weight: 344.408
• Mol File: 29388-33-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Phenol,4,4'-[[(3R,4R)-tetrahydro-3,4-furandiyl]bis(methylene)]bis[2-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol,4,4'-[[(3R,4R)-tetrahydro-3,4-furandiyl]bis(methylene)]bis[2-methoxy-(29388-33-8)
• EPA Substance Registry System: Phenol,4,4'-[[(3R,4R)-tetrahydro-3,4-furandiyl]bis(methylene)]bis[2-methoxy-(29388-33-8)

Safety Data

• Hazardous Substances Data: 29388-33-8(Hazardous Substances Data)

Usage

General Description

Phenol,4,4'-[[(3R,4R)-tetrahydro-3,4-furandiyl]bis(methylene)]bis[2-methoxy- is a chemical compound with the molecular formula C22H26O6. It is a derivative of phenol and is composed of two methylene groups linked by a furandiyl ring. The compound also contains two methoxy groups attached to the phenol ring. It has potential applications in the field of organic chemistry and may be used as a building block for the synthesis of more complex organic molecules. Additionally, it may have potential uses in pharmaceuticals or other industries that require specialty chemicals.

Upstream product

• 484-39-9 liovil 
• 3688-23-1 (-)-secoisolariciresinol 
• 486-29-3 lariciresinol 
• 141-78-6 ethyl acetate 
• 580-72-3 matairesinol 
• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 111194-08-2 (8R,8'R)-4,4'-dibenzyloxy-3,3'-dimethoxylignane-9,9'-diol 
• 111266-03-6 (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 
• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 111265-99-7 C₁₃H₁₄O₆^(2-)*2K⁽¹⁺⁾ 
• 111194-07-1 (3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one 
• 868127-98-4 (3R,4R)-3-(4-benzyloxy-3-methoxybenzyl)-4-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]tetrahydrofuran 
• 868127-97-3 (3R,4R)-3-(4-benzyloxy-3-methoxybenzyl)-4-[(R)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]tetrahydrofuran 

Relevant articles and documents

Effect of benzylic oxygen on the antioxidant activity of phenolic lignans

It has been clarified in the present investigation that a high degree of oxidation at the benzylic position of phenolic lignans bearing a 4-hydroxy-3-methoxybenzyl group reduces their antioxidant activity and that the antioxidant activity of the bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran lignan 2 is higher than that of the corresponding y-butyrolactone lignan 1. This was demonstrated by comparing the antioxidant activities of compounds 1 and 2 with those of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4, the bis(hydroxybenzyl)tetrahydrofurans 7 and 8, the (benzoyl)(benzyl)tetrahydrofuran 6, and the dibenzoyltetrahydrofuran 9. The activity level of compound 2 was approximately the same potency as that of the tetrahydronaphthalene- tetrahydrofuran 5. These compounds possess either a 4-hydroxy-3-methoxybenzyl group or a 4-hydroxy-3-methoxybenzoyl group as the benzyl or benzoyl group. An examination of radical scavenging activity showed differences of activity between diastereomers. To make this comparison possible, compounds 1-9 were synthesized using new synthetic routes for several of these lignans. In this investigation, stereoisomers of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4 and liovils 7 and 8 were synthesized for the first time.

(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase

The natural dibenzylbutyrolactone type lignanelide (-)-arctigenin (2), an inhibitor of human irnmunodeficiency virus type-1 (HIV-1) replication in infected human cell systems, was found to suppress the integration of proviral DNA into the cellular DNA genome. In the present study 2 was tested with purified HIV-1 integrase and found to be inactive in the cleavage (3'- processing) and integration (strand transfer) assays. However, the semisynthetic 3-O-demethylated congener 9 characterized by a catechol substructure exhibited remarkable activities in both assays. Structure- activity relationship studies with 30 natural (1-6), semisynthetic (7-21), and synthetic (37-43, 45, 46) lignans revealed that (1) the lactone moiety is crucial since compounds with a butane-1,4-diol or tetrahydrofuran substructure and also lignanamide analogues lacked activity and (2) the number and arrangement of phenolic hydroxyl groups is important for the activity of lignanolides. The congener with two catechol substructures (7) was found to be the most active compound in this study. 7 was also a potent inhibitor of the 'disintegration' reaction which models the reversal of the strand transfer reaction. The inhibitory activity of 7 with the core enzyme fragment consisting of amino acids 50-212 suggests that the binding site of 7 resides in the catalytic domain.