14464-90-5

Usage

Uses

Used in Pharmaceutical Development:
(1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol is used as a pharmaceutical candidate for its potential antioxidant properties, which can be beneficial in the treatment of various diseases and conditions associated with oxidative stress.
Used in Organic Synthesis:
In the field of organic synthesis, (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol serves as a valuable precursor for the synthesis of other complex organic molecules, leveraging its unique structure and functional groups.
Used in Antioxidant Applications:
(1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol is used as an antioxidant agent, providing protection against oxidative damage in various industrial and biological systems, thereby enhancing the stability and longevity of products and organisms.
Used in Chemical Research:
In the realm of chemical research, (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol is utilized as a subject of study to explore its unique properties, reactivity, and potential applications in various chemical processes and reactions.

Upstream product

• 27193-56-2 (+/-)-Lyoniresinol 2α-O-rhamnoside 
• 62058-46-2 (-)-lyoniresinol 9′-O-β-xylopyranoside 

Downstream Products

• 23212-65-9 DL-Dimethoxy-isolariciresinol-tetraacetat 
• 75658-16-1 (+)-Lyoniresinol-7,4'-dimethylether 
• 7333-11-1 rac.-1r,2t,3c-Lyoniresinol-7,4'-dimethylether 
• 54712-60-6 lyoniresinol dimethyl ether 

Relevant academic research and scientific papers

A new lignan glycoside and phenylethanoid glycosides from Strobilanthes cusia BREMEK

The root of Strobilanthes cusia BREMEK. (Acanthaceae), popularly known as Da-Ching-Yeh, has been commonly used in traditional Chinese medicine. It is used to treat influenza, epidemic cerebrospinal meningitis, encephalitis B, viral pneumonia, mumps, and severe acute respiratory syndrome (SARS). In this study, we found a new lignan glycoside (6) and two new phenylethanoid glycosides (7, 8) together with five known compounds as chemical constituents of Strobilanthes cusia root. Some samples were examined for anti-herpes simplex virus type-1 (HSV-1) activity. Among the tested samples, lupeol showed anti-HSV-1 activity (EC50: 11.7 μM) and showed 100% inhibition of virus plaque formation at 58.7 μM.

Three new lignan derivatives from Lindera glauca (Siebold et Zucc.) blume

Two new aryl-tetralin lignan glycosides, linderanosides A and B (1 and 2, resp.), and a new dihydrobenzofuran neolignan glycoside, linderanoside C (3), together with five known lignan derivatives (4-8) were isolated from the trunk of Lindera glauca. The structures of these new compounds were determined through spectroscopic analyses, including extensive 2D-NMR data and acid hydrolysis. The absolute configurations of the compounds were clarified by circular dichroism (CD) spectroscopic studies. Compounds 1-8 were evaluated for their cytotoxicity against A549 (non-small cell lung adenocarcinoma), SK-OV-3 (ovarian cancer cells), A498 (human kidney epithelial cells), and HCT-15 (colon cancer cells) human tumor cell lines using sulforhodamine B assays in vitro.

Phenolic constituents from the twigs of Betula schmidtii collected in Goesan, Korea

Six undescribed phenolic derivatives along with thirty two known compounds were isolated from the twigs of Betula schmidtii. The chemical structures were characterized through extensive spectroscopic analysis and chemical methods. All known compounds were first isolated in this plant. The anti-inflammatory effect of the isolates was tested by measuring nitric oxide production in lipopolysaccharide-activated BV-2 cells. Isotachioside, 4-allyl-2-hydrophenyl 1-O-β-D-apiosyl-(1 → 6)-β-D-glucopyranoside, genistein 5-O-β-D-glucoside, and prunetinoside showed a slight potency to lower the NO production against LPS-activated microglia with IC50 values of 23.9, 25.3, 28.8, and 34.0 μM, respectively.

Taste-guided isolation of bitter lignans from Quercus petraea and their identification in wine

Quercoresinosides A and B (1 and 2), two new lignans, were isolated from a toasted Quercus petraea heartwood extract along with a known compound, 3-methoxy-4-hydroxyphenol 1-O-β-d-(6′-O-galloyl)glucopyranoside (3). The purification protocol was based on a taste-guided approach that sought to reveal new bitter compounds released from oak wood into wines and spirits. HRMS and NMR data were used to establish that compounds 1 and 2 are lignan derivatives bearing a glucosyl unit and a galloyl unit at the same positions. Hydrolysis of these compounds showed that they could be distinguished by the absolute configuration of their respective lyoniresinol genin as determined by chiral LC-HRMS in comparison with (+)- and (-)-lyoniresinol standards. Sensory analyses were performed in a non-oaked wine on the pure compounds 1-3. The three molecules exhibited a bitter taste at 2 mg/L that was particularly intense for compounds 2 and 3. Finally, LC-HRMS demonstrated the occurrence of compounds 1-3 in oaked wine and brandy, which supports the hypothesis of their contributions to the increase in bitterness during oak aging.

Indonesian medicinal plants. XII. Four isomeric lignan-glucosides from the bark of Aegle marmelos (Rutaceae)

From the bark of Aegle marmelos Correa (Rutaceae), an Indonesian medicinal plant, two new lignan-glucosides, ( )-lyoniresinol 2α-O-β-D-glucopyranoside (3) and (-)-4-epi-lyoniresinol 3α-O-β-D-glucopyranoside (4), have been isolated together with two known lignan-glucosides, (+)-lyoniresinol 3α-O-β-D-glucopyranoside (1) and (-)lyoniresinol 3α-O-β-D-glucopyranoside (2).

Total Asymmetric Synthesis and Stereochemical Confirmation of (+)- and (-)-Lyoniresinol and Its Deuterated Analogues

Lyoniresinol and its derivatives are lignans which have been isolated from a plethora of plant species. In addition to exhibiting a range of interesting biological activities including anticancer, anti-inflammatory, antimicrobial, and others, these compounds have also been discovered in wines and spirits and shown to have gustatory effects in these alcoholic matrices. (+)-Lyoniresinol 1 is reported to impart a strong bitter taste while its enantiomer (-)-lyoniresnol 2 is tasteless. The first total asymmetric synthesis of both natural enantiomers (+)-1 and (-)-2 and their deuterated analogues (D4)-(+)-3 and (D4)-(-)-4 has been achieved, confirming the structure and stereochemistry of the natural products. The synthesized compounds can be utilized as internal standards in stable isotope dilution analysis for improving and optimizing the existing lyoniresinol quantitation methods in the future.

Novel tetrahydrofuran structures derived from β-β-coupling reactions involving sinapyl acetate in Kenaf lignins

Free radical coupling of sinapyl γ-acetate or cross-coupling between sinapyl acetate and sinapyl alcohol yields novel tetrahydrofuran β-β-(cross-)coupled dehydrodimers. Such substructures are therefore anticipated in naturally acetylated lignins, e.g. in Kenaf, if sinapyl acetate is a component of the lignin monomer pool. The DFRC (derivatization followed by reductive cleavage) method, modified by replacing all acetyl reagents and solvents with their propionyl analogs (DFRC′), allows the analysis of naturally acetylated lignins. DFRC′ treatment of the sinapyl acetate-derived dimers or crossed dimers gave diagnostic products that retain at least one acetate group on a sidechain γ-position; the products have been authenticated by comparison of their mass spectra and GC retention times with those of synthesized compounds. DFRC′ of Kenaf lignins produces the same diagnostic products as from the dimers, implicating the presence of the various tetrahydrofuran units in Kenaf lignins. With data from the model compounds in hand, NMR analysis of Kenaf lignins elegantly confirms the presence of such substructures in the polymer, establishing that acetates on Kenaf lignins arise through incorporation of sinapyl acetate, as a lignin precursor, via enzyme-mediated radical coupling mechanisms. The Royal Society of Chemistry 2008.

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

The constituents of Betula ermanii CHAM. in Japan were identified as follows. Fresh leaves: 20(S),24(R)-epoxydammmaran-3β,11α,25-triol (1), 3- O-β-D-glucopyranoside of 1 (2), 2'-acetate of 2 (3), 11,2'-diacetate of 2 (4), dammar-24-en-3β,11α,20(S)-triol (5), 3-O-β-D-2-O- acetylglucopyranoside of 5 (6). Outer bark: betulin (7), betulin 3-caffeate (8), oleanolic acid (9). Inner bark: (+)-lyoniresinol 3α-O-α-L- rhamnopyranoside (10), (-)-lyoniresinol 3α-O-β-D-xylopyranoside (11), 9,9'- di-O-feruloyl-(-)-secoisolariciresinol (12), acerogenin E (13), 3,4,5- trimethoxyphenol β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (14), 4-(4- hydroxyphenyl)-2-butanol 2-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (15), (+)-catechine 7-O-β-D-xylopyranoside (16), lupeol (17), monogynol A (18). Root outer bark: lupeol caffeate (19), betulin 3-caffeate (8), oleanolic acid caffeate (20), dammarendiol II 3-caffeate (21). Compounds 2, 3, 4, 6, 19 and 21 are new.

TWO DIARYLHEPTANOIDS AND A LIGNAN FROM CASUARINA JUNGHUHNIANA

A new diarylheptanoid, casuarinondiol and two known compounds, alnusdiol (a further diarylheptanoid) and (+/-)-lyoniresinol 2α-O-rhamnoside (a lignan), have been isolated from the roots of Casuarina junghuhniana and characterized spectroscopically.These a

Pygeoside, a New Lignan Xyloside from Pygeum acuminatum

Pygeoside, a new lignan xyloside has been isolated from Pygeum acuminatum Coleb. and characterized.The aglycone, pygeoresinol, has been shown to be a hitherto unkonown diastereomer, (-)-lyoniresinol, by physico-chemical evidences.On the basis of PMR data the glycoside has been assigned the structure (-)-lyoniresinol-2-xyloside.