85699-62-3

Basic information

• Product Name: alfa-Conidendrin
• Synonyms: alfa-Conidendrin
• CAS NO: 85699-62-3
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.3692
• Mol File: 85699-62-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 601.4°Cat760mmHg
• Flash Point: 218.1°C
• Appearance: /
• Density: 1.334g/cm³
• Vapor Pressure: 4.65E-15mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: alfa-Conidendrin(CAS DataBase Reference)
• NIST Chemistry Reference: alfa-Conidendrin(85699-62-3)
• EPA Substance Registry System: alfa-Conidendrin(85699-62-3)

Safety Data

• Hazardous Substances Data: 85699-62-3(Hazardous Substances Data)

Usage

General Description

Alfa-conidendrin is a naturally occurring sesquiterpene chemical compound found in a variety of plants, such as conifers and eucalyptus. It is known for its anti-inflammatory, antinociceptive, and inotropic effects, as well as its potential use in the treatment of inflammatory diseases. Alfa-conidendrin has been studied for its ability to inhibit the production of pro-inflammatory cytokines, such as TNF-alpha and IL-6, and to reduce pain and inflammation in animal models. It also exhibits cardiotonic properties, making it potentially useful in the treatment of heart conditions. Additionally, alfa-conidendrin has shown antimicrobial activity against certain pathogens, making it a promising compound for the development of new anti-inflammatory and antimicrobial drugs.

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 
• 127951-05-7 (2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 20268-71-7 (7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone 
• 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 
• 111266-00-3 (R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 127951-00-2 (3R)-(+)-3-(4-Trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 127951-01-3 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-03-5 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 347359-71-1 (7RS,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylignano-9,9'-lactone 
• 127951-05-7 (+/-)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 

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 
• 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.