(1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol

Base Information

• Chemical Name: (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol
• CAS No.: 14464-90-5
• Molecular Formula: C₂₂H₂₈O₈
• Molecular Weight: 420.46
• Mol file: 14464-90-5.mol

Synonyms:2,3-Naphthalenedimethanol,1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-,[1S-(1a,2b,3a)]-; Lyoniresinol (7CI,8CI); (+)-Lyoniresinol; Lyoniresinol, (+)-

Chemical Property of (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol

Chemical Property:

• Melting Point: 170.7-171.0 °C
• Boiling Point: 617.6±55.0 °C(Predicted)
• PKA: 10.05±0.40(Predicted)
• PSA: 117.84000
• Density: 1.272±0.06 g/cm3(Predicted)
• LogP: 2.03720

Purity/Quality:

99% ^*data from raw suppliers

(+)-lyoniresinol 98 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol, also known as (+)-lyoniresinol, is a lignan identified in *Betula ermanii*. It is part of a broader group of bioactive compounds, including triterpenes and phenolics, found in the tree's leaves, bark, and root bark. (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol, along with its enantiomer (-)-lyoniresinol, contributes to the medicinal potential of *Betula* species, aligning with their traditional uses in medicine and cosmetics.

Technology Process of (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol

There total 17 articles about (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(1RS,2SR)-7-benzyloxy-1,2-dihydro-1-(4-benzyloxy-3,5-dimethoxyphenyl)-2,3-bis(hydroxymethyl)-6,8-dimethoxynaphthalene → (-)-(7R,8S,8'S)-lyoniresiol, racemic form (3737-93-7,14464-90-5,23212-64-8,31768-94-2,73745-49-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 10h;

DOI:10.1039/b809464k

Reference yield: 72.0%

(3aS,9R,9aS)-7-hydroxy-9-(4'-hydroxy-3',5'-dimethoxyphenyl)-6,8-dimethoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one → (-)-(8S,8'S,7'S)-lyoniresinol (3737-93-7,14464-90-5,23212-64-8,73745-49-0,31768-94-2)

Guidance literature:

With lithium aluminium hydride; In tetrahydrofuran; at 0 ℃; for 4.5h; Inert atmosphere;

DOI:10.1021/acs.joc.1c03085

Reference yield: 70.0%

(3aR,9S,9aR)-7-hydroxy-9-(4′-hydroxy-3′,5′-dimethoxyphenyl)-6,8-dimethoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one → (+)-lyoniresinol (3737-93-7,23212-64-8,31768-94-2,73745-49-0,14464-90-5)

Guidance literature:

With lithium aluminium hydride; In tetrahydrofuran; at 0 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.joc.1c03085

upstream raw materials:

(+/-)-Lyoniresinol 2α-O-rhamnoside

(-)-lyoniresinol 9′-O-β-xylopyranoside

Downstream raw materials:

lyoniresinol dimethyl ether

rac.-1r,2t,3c-Lyoniresinol-7,4'-dimethylether

DL-Dimethoxy-isolariciresinol-tetraacetat

(+)-Lyoniresinol-7,4'-dimethylether

Refernces

Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii

10.1248/cpb.43.1937

The research focused on the chemical evaluation of Betula species in Japan, specifically the constituents of Betula ermanii. The purpose of the study was to identify and characterize the chemical compounds present in different parts of the tree, including the fresh leaves, outer bark, inner bark, and root bark. The research concluded that the tree contained a variety of dammarane-type triterpenes, lignans, triterpenes, phenolics, and caffeoyl esters. Some of the key chemicals identified were 20(S),24(R)-epoxydammaran-3,11x,25-triol and its derivatives, betulin, betulin 3-caffeate, oleanolic acid, and various lignans such as (+)-lyoniresinol and (-)-lyoniresinol. The study also reported several new compounds, including 2, 3, 4, 6, 19, and 21, which were dammarane-type glycosides isolated for the first time from the leaves of Betula species. This comprehensive analysis of Betula ermanii's chemical constituents contributes to the understanding of its potential medicinal value, building on the known traditional uses of other Betula species in medicine and cosmetics.