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

Uses

Different sources of media describe the Uses of 518-55-8 differently. You can refer to the following data:
1. (-)-ALPHA-CONIDENDRIN is a plant derived lignan that may be used as a source or reference compound to study bacteria that degrade plant lignans. (-)-ALPHA-CONIDENDRIN may be used as a starting material for the synthesis of sikkimotoxin derivatives and cytotoxic metabolites.
2. Conidendrin is an antioxidant lignan found in trees that is also present as a component of fine particle emissions from the fireplace combustion of 6 species of woods grown in the northeastern USA.

Definition

ChEBI: A natural product found in Taxus yunnanensis.

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

• 101312-79-2 (1S,3aR,4S,9aR)-1,7-dimethoxy-4-(4'-hydroxy-3'-methoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho<2,3-c>furan-6-ol 
• 71724-99-7 (1R,3aR,4S,9aR)-1,7-dimethoxy-4-(4'-hydroxy-3'-methoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho<2,3-c>furan-6-ol 
• 140193-27-7 (-)-O-6-Benzyl-α-conidendrine 
• 127951-05-7 (2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 553642-24-3 6-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-7-methoxy-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one 
• 20268-71-7 (7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 
• 689277-80-3 (-)-(2S,5S)-2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-en-1-ol 
• 689277-79-0 (+)-4-benzyl-3-(2-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}but-3-enoyl)oxazolidin-2-one 
• 689277-82-5 (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester 
• 689277-83-6 (-)-8-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}-8'-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxybenzyl]dihydrofuran-2-one 
• 553642-33-4 (E)-methyl (4-tert-butyldimethylsilyloxy-3-methoxyphenyl)vinyldiazoacetate 
• 553642-30-1 (R)-(E)-methyl 2-(4-tert-butyldimethylsilyloxy-3-methoxybenzyl)-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)but-3-enoate 
• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 

Downstream Products

• 5474-93-1 3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one 
• 5447-65-4 O-diacetyl-(+/-)-α-conidendrine 
• 25047-22-7 (-)-O-Diacetyl-α-conidendrine 
• 5234-71-9 (6R,7R,8S)-isolariciresinol 
• 71772-18-4 α-conidendrin dimethyl ether 
• 21966-92-7 isolariciresinol dimethyl ether 
• 321747-12-0 dimethyl-4-iso-α-conidendrol 
• 321747-11-9 [(1S,9R,12R)-1-(3,4-Dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl]-methanol 
• 321747-13-1 Acetic acid (1S,9R,12R)-1-(3,4-dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-ylmethyl ester 
• 321747-14-2 tert-Butyl-[(1S,9R,12R)-1-(3,4-dimethoxy-phenyl)-4,5-dimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-ylmethoxy]-dimethyl-silane 
• 26194-59-2 anhydroisolariciresinol 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 

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.