518-55-8

Basic information

• Product Name: (-)-ALPHA-CONIDENDRIN
• Synonyms: (-)-ALPHA-CONIDENDRIN;conidendrin;(3aR)-3aβ,4,9,9aα-Tetrahydro-6-hydroxy-4β-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one;(3aR)-4β-(4-Hydroxy-3-methoxyphenyl)-6-hydroxy-7-methoxy-3,3aβ,4,9-tetrahydronaphtho[2,3-c]furan-1(9aαH)-one;3aβ,4,9,9aα-Tetrahydro-4β-(3-methoxy-4-hydroxyphenyl)-6-hydroxy-7-methoxynaphtho[2,3-c]furan-1(3H)-one;(3aR,4S,9aR)-3a,4,9,9a-Tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one;(3aR,4S,9aR)-6-Hydroxy-4-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one;NSC 4586
• CAS NO: 518-55-8
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.37
• Mol File: 518-55-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 254-255 °C
• Boiling Point: 601.4 °C at 760 mmHg
• Flash Point: 218.1 °C
• Appearance: /
• Density: 1.334 g/cm³
• Vapor Pressure: 4.65E-15mmHg at 25°C
• Refractive Index: 1.618
• PKA: 9.95±0.40(Predicted)
• CAS DataBase Reference: (-)-ALPHA-CONIDENDRIN(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ALPHA-CONIDENDRIN(518-55-8)
• EPA Substance Registry System: (-)-ALPHA-CONIDENDRIN(518-55-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 518-55-8(Hazardous Substances Data)

Usage

Description

(-)-ALPHA-CONIDENDRIN, also known as Conidendrin, is a plant-derived lignan primarily found in Taxus yunnanensis. It is a natural product with potential applications in various fields due to its unique chemical properties.

Uses

Used in Research and Development:
(-)-ALPHA-CONIDENDRIN is used as a source or reference compound for studying bacteria that degrade plant lignans. This helps in understanding the biological processes and interactions involving lignans in the environment.
Used in Synthesis:
(-)-ALPHA-CONIDENDRIN is used as a starting material for the synthesis of sikkimotoxin derivatives and cytotoxic metabolites. These synthesized compounds can be further explored for their potential applications in pharmaceuticals and other industries.
Used in Environmental Studies:
Conidendrin, a form of (-)-ALPHA-CONIDENDRIN, is an antioxidant lignan found in trees and is also present as a component of fine particle emissions from the fireplace combustion of six species of woods grown in the northeastern USA. This makes it relevant for studying the environmental impact of wood combustion and the role of lignans in air quality and pollution.
Used in Pharmaceutical Research:
(-)-ALPHA-CONIDENDRIN, due to its unique chemical structure and natural origin, can be a potential candidate for pharmaceutical research. Its exploration in drug development could lead to the discovery of new therapeutic agents with various applications in medicine.

InChI:InChI=1/C20H20O6/c1-24-17-6-10(3-4-15(17)21)19-12-8-16(22)18(25-2)7-11(12)5-13-14(19)9-26-20(13)23/h3-4,6-8,13-14,19,21-22H,5,9H2,1-2H3/t13-,14+,19+/m1/s1

Upstream product

• 140193-27-7 (-)-O-6-Benzyl-α-conidendrine 
• 89067-60-7 (d,l)-O-dibenzyl α-conidendrine 
• 89067-57-2 (benzoxy-4 methoxy-3)benzyl-2(benzoxy-4 methoxy-3 α,α-propylenedithio)benzyl-3 butanolide 
• 89067-58-3 (+/-)-trans-2-(3-methoxy-4-benzyloxybenzyl)-3-(3'-metyhoxy-4'-benzyloxy-α-benzoyl)butyrolactone 
• 89067-59-4 O-dibenzylhydroxymatairesinol 
• 105783-66-2 (benzoxy-4 methoxy-3 α,α-propylene dithio)benzyl-3 butanolide 
• 50766-69-3 2-(4-benzyloxy-3-methoxyphenyl)-1,3-dithiane 
• 72724-00-6 1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene 
• 89067-60-7 O-dibenzyl-β-conidendrine 
• 127951-04-6 (+/-)-2-(4-Benzyloxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-03-5 (+/-)-3-(α-Benzyloxy-4-trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 911805-41-9 (+/-)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-00-2 (+/-)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 84755-40-8 (hydroxy-4 methoxy-3 benzyl)-4 dihydro-3H-furannone-2 

Downstream Products

• 71772-18-4 α-conidendrin dimethyl ether 
• 2316-10-1 3',4,4',5-tetrahydroxy-2,7'-cyclolignan-9,9'-lactone 
• 78178-29-7 α-conidendreic acid dimethyl ester dimethyl ether 
• 1403982-14-8 9',9'-diphenyldimethylcyclolariciresinol 
• 1422430-60-1 9',9'-diphenyldimethylretrodendrin 
• 1422430-59-8 C₄₀H₃₈O₆ 
• 1422430-67-8 C₄₀H₃₈O₅ 
• 1428415-59-1 C₄₀H₃₆O₅ 
• 1422430-61-2 9-O-benzyl-9',9'-diphenyldimethylcyclolariciresinol 
• 1422430-62-3 9’-O-methyl-9-O-benzyl-9',9'-diphenyldimethylcyclolariciresinol 
• 1422430-63-4 9’-O-methyl-9',9'-diphenyl-dimethylcyclolariciresinol 
• 1422430-72-5 C₃₇H₄₄O₆Si 
• 1422430-73-6 C₄₀H₅₀O₆Si 
• 1422430-74-7 C₃₇H₄₀O₆ 

Relevant articles and documents

Syntheses of all eight stereoisomers of conidendrin

All eight stereoisomers of conidendrin were synthesized from (1 R,2 S,3 S)-1-(4-benzyloxy-3-methoxyphenyl)-3-(4-benzyloxy-3-methoxybenzyl)-2- hydroxymethyl-1,4-butanediol ((+)-4) and its enantiomer with high optical purity. The configurations at 4-positio

Derivatives of the Lignan 7′-Hydroxymatairesinol with Antioxidant Properties and Enhanced Lipophilicity

The lignan 7′-hydroxymatairesinol (1), extracted from the knotwoods of fir (Abies alba), spruce (Picea abies), and Douglas fir (Pseudotsuga menziesii), exhibited unexpected reactivity when esterification reactions were attempted on the hydroxy group at position C-7′. To circumvent the rapid intramolecular cyclization procedure, leading quantitatively to the lignan conidendrin (7), a simple strategy for 7′-esterification of 1 under mild conditions (three steps, up to 80% overall yield) was developed. Compared to hydroxymatairesinol (1) (log K′w = 1.49), the derivatives (2-5) had increased lipophilicity with log K′w > 3.1, as determined by a UHPLC method. Compounds 1-5 exhibited potent antioxidant properties in the same range as the standards ascorbic acid and α-tocopherol (IC50 = 20-25 μM) and higher than that of BHT using a DPPH radical-scavenging assay.

Synthesis and structural analysis of sterically hindered chiral 1,4-diol ligands derived from the lignan hydroxymatairesinol

The readily available natural lignan hydroxymatairesinol was transformed into sterically hindered and optically pure diphenyl, di-2-naphthyl, and tetramethyl 1,4-diol derivatives via arylation/alkylation of the aryltetralinbutyrolactone lignan (-)-conidendrin. In addition, the diastereoselective formation of stable hemiketals from the highly substituted butyrolactone was studied in detail. The conformations of the molecules prepared were studied computationally at molecular mechanics (MM), Hartree-Fock (HF)/6-31G*, and (DFT/B3LYP/TZVP) levels including entropy contributions and by NMR-spectroscopy. The conformations adopted showed that these novel chiral 1,4-diols may be suitable as chiral ligands for the development of new chiral transition metal and organo catalysts.