83327-19-9

Basic information

• Product Name: Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanemethanol
• Synonyms: Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanemethanol;3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydrox y-3-methoxyphenyl)methyl)-, (2R-(2alpha,3beta,4beta))-;Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanmethanol;LARICIRESINOL(P)
• CAS NO: 83327-19-9
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.40096
• Mol File: 83327-19-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 568.4°C at 760 mmHg
• Flash Point: 297.6°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 9.26E-14mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanemethanol(83327-19-9)
• EPA Substance Registry System: Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanemethanol(83327-19-9)

Safety Data

• Hazardous Substances Data: 83327-19-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2R,3S,4S-diastereomer).

InChI:InChI=1/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1

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 
• 91-20-3 naphthalene 
• 108-88-3 toluene 
• 29388-33-8 (3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)-4-butanolide 
• 67560-68-3 tetrahydro-2-(3,4-dimethoxyphenyl)-4-<(3,4-dimethoxyphenyl)methyl>-3-furanmethanol 

Relevant articles and documents

Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties

Two western red cedar pinoresinol-lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8- and 8′-linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can enantiospecifically metabolize different furofuran lignans with modified aromatic ring substituents, but where phenolic groups at both C4/C4′ are essential for catalysis. These results are consistent with quinone methide intermediate formation in the PLR active site. Site-directed mutagenesis and kinetic measurements provided additional insight into factors affecting enantioselectivity and kinetic properties. From these data, PLRs can be envisaged to allow for the biotechnological potential of generation of various lignan skeleta, that could be differentially “decorated” on their aromatic ring substituents, via the action of upstream dirigent proteins.

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.