486-29-3

Basic information

• Product Name: (+)-lariciresinol
• CAS NO: 486-29-3
• Molecular Weight: 360.407
• Mol File: 486-29-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (+)-lariciresinol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-lariciresinol(486-29-3)
• EPA Substance Registry System: (+)-lariciresinol(486-29-3)

Safety Data

• Hazardous Substances Data: 486-29-3(Hazardous Substances Data)

Upstream product

• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 92831-74-8 4-<<4-(benzyloxy)-3-methoxyphenyl>methyl>dihydro-2(3H)-furanone 
• 112747-98-5 7S,8R,8'R-(-)-Lariciresinol-4,4'-bis-O-β-D-glucopyranoside 
• 112747-98-5 clemastanin B 
• 143663-00-7 (+)-lariciresinol 4'-O-β-D-glucopyranoside 

Downstream Products

• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 121-33-5 vanillin 
• 5502-30-7 7-acetoxy-1-(4-acetoxy-3-methoxy-phenyl)-2,3-bis-acetoxymethyl-6-methoxy-1,2,3,4-tetrahydro-naphthalene 
• 95810-25-6 (4-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)tetrahydrofuran-3-yl)methanol 
• 4097-63-6 2-methoxy-4,6-dinitrophenol 
• 4676-53-3 optically inactive 6,7-dimethoxy-2,3-bis-hydroxymethyl-1-(3,4-dimethoxy-phenyl)-tetralin 
• 5234-71-9 isolariciresinol 
• 63015-84-9 4-(4-Hydroxy-3-methoxy-phenyl)-7-methoxy-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-ol 
• 90-05-1 2-methoxy-phenol 
• 91-57-6 2-Methylnaphthalene 
• 67560-67-2 (+)-lareciresinol triacetate 
• 91-20-3 naphthalene 
• 108-88-3 toluene 
• 29388-33-8 (3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)-4-butanolide 

Relevant articles and documents

Effect of the benzylic structure of lignan on antioxidant activity

The effect of the benzylic structure of lignan on antioxidant activity was evaluated. Secoisolariciresinol (1) and 3,4-bis(4-hydroxy-3-methoxybenzyl) tetrahydrofuran (2), which have two secondary benzylic positions without oxygen, showed the highest antioxidant activity. Optically active verrucosin (4) was synthesized for the first time in this experiment.

Synthetic transformation of hydroxymatairesinol from Norway spruce (picea abies) to 7-hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol

We have developed a method for the transformation of hydroxymatairesinol to optically pure (+)-lariciresinol and (+)-cyclolariciresinol via the hitherto unreported lignan 7-hydroxysecoisolariciresinol. The two naturally occurring isomers of hydroxymatairesinol were reduced with LiAlH4 to a mixture of two epimers of 7-hydroxysecoisolariciresinol, which were further selectively transformed to (+)-lariciresinol and (+)-cyclolariciresinol by an acid catalysed intramolecular cyclisation reaction. The structure of the major isomer of 7-hydroxysecoisolariciresinol was confirmed by X-ray crystallography and thereby also the absolute configurations of the two isomers of hydroxymatairesinol were unambiguously proven. Optical purities were determined by chiral HPLC-MS/MS and optical rotation measurements.

Lignan bis-glucosides from Galium sinaicum

The new lariciresinol-based lignan bis-glucosides, 7S, 8R, 8'R-(-)- Iariciresinol-4,4'-bis-O-β-D-glucopyranoside and 7S, 8R, 8'R-(-)-5- methoxylariciresinol-4,4'-bis-O-β-D-glucopyranoside, together with (-)- syringaresinol-4,4'-bis-O-β-D-glucopyranoside were isolated from the n- butanol extract of Galium sinaicum roots and their structures were established by various spectroscopic techniques. The isolated compounds represent the first report of lignan glycosides from the Rubiaceae. The two lariciresinol-type glucosides exhibited weak cytotoxic activity against the P388 cell line.