526-06-7

Basic information

• Product Name: EUDESMINE
• Synonyms: eudesmin;(1R,3aα,6aα)-1,4α-Bis(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan;(1R,3aα,6aα)-1α,4α-Bis(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan;(3aβ,6aβ)-3β,6β-Bis(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan;(+)-Pinoresinol dimethyl ether;(1S)-3aβ,4,6,6aβ-Tetrahydro-1β,4β-bis(3,4-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan;Pinoresinol dimethyl ether;NSC 35476
• CAS NO: 526-06-7
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.441
• Mol File: 526-06-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 108.5-109.5℃
• Boiling Point: 517.3°Cat760mmHg
• Flash Point: 209.8°C
• Appearance: /
• Density: 1.173g/cm³
• Vapor Pressure: 2.72E-10mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: 2-8°C
• CAS DataBase Reference: EUDESMINE(CAS DataBase Reference)
• NIST Chemistry Reference: EUDESMINE(526-06-7)
• EPA Substance Registry System: EUDESMINE(526-06-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 526-06-7(Hazardous Substances Data)

Usage

Description

Cineole can be obtained by extraction from natural plants, such as Umbelliferae, Rutaceae, Aurelianaceae, Magnoliaceae, Daphneaceae.

Uses

Eudesmin is used in the bioguided isolation identification and activity evaluation of antifungal compounds from Acorus tatarinowii Schott.

Application

Eucalyptol is a alleviating renal fibrosis drug via inhibiting TGFβ1, thereby achieving the purpose of alleviating renal fibrosis in humans or experimental animals.

General Description

Natural product derived from plant source.

Biochem/physiol Actions

Eudesmin is a component of a Brazilian folk medicine that has been used for blood pressure reduction. Eudesmin also is an inhibitor of TNF-alpha production and T cell proliferation.

InChI:InChI=1/C22H26O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-28-22(16(15)12-27-21)14-6-8-18(24-2)20(10-14)26-4/h5-10,15-16,21-22H,11-12H2,1-4H3/t15-,16-,21+,22+/m1/s1

Upstream product

• 135735-08-9 (3R,4S,5S,6αRS)-3-<(3,4-Dimethoxyphenyl)hydroxymethyl>-4-<(3,4-dimethoxyphenyl)bis(phenylthio)methyl>-5-(d-menthyloxy)dihydro-2(3H)-furanone 
• 186581-53-3 diazomethane 
• 340167-81-9 rel-(7α,7'α,8α,8'α)-7,9':7',9-diepoxylignane-3,3',4,4'-tetraol 
• 72536-33-5 4,8-dihydroxypinoresinol 
• 911858-80-5 (3S,3aS,6S,6aS)-3,6-Bis-(3,4-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-diol 
• 4263-88-1 pinoresinol 
• 63281-70-9 2,6-bis-(4-acetoxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-4,8-dione 
• 72536-38-0 4,8-dimethoxyeudesmin 
• 72536-37-9 4,8-dimethoxypinoresinol 
• 72536-34-6 4,8-dihydroxyeudesmin 
• 38209-42-6 threo-2,3-bis-(α-hydroxy-4-hydroxy-3-methoxybenzyl)butane-1,4-diol 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 115754-03-5 4-((E)-3-Bromo-propenyl)-1,2-dimethoxy-benzene 
• 438581-68-1 1-(3,4-dimethoxyphenyl)-1-(3-(3,4-dimethoxyphenyl)-2-propenyloxy)-2,3-epoxypropane 

Downstream Products

• 81446-29-9 (-)-pinoresinol 
• 487-39-8 (+)-pinoresinol monomethyl ether 
• 60102-89-8 (+)-epipinoresinol dimethyl ether 
• 20610-45-1 (3aS)-1c,4t-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 
• 20610-45-1 (3aR)-1c,4t-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 
• 93-07-2 Veratric acid 
• 3395-03-7 4,5-dimethoxy-1,2-dinitrobenzene 
• 4676-33-9 3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)furan 
• 21966-92-7 isolariciresinol dimethyl ether 
• 4263-88-1 pinoresinol 
• 67560-68-3 tetrahydro-2-(3,4-dimethoxyphenyl)-4-<(3,4-dimethoxyphenyl)methyl>-3-furanmethanol 

Relevant articles and documents

Stereoselective total synthesis of furofuran lignans through dianion aldol condensation

Highly stereoselective total synthesis of (+)-eudesmin, (+)-yangambin, (-)-eudesmin, and (-)-yangambin is described. This method is useful to generate the core skeleton of furofuran rings utilizing modification of Evans asymmetric aldol condensation.

Sesquineolignans and other constituents from the seeds of Joannesia princeps

From the as extract of the seeds of the Brazilian Joannesia princeps 3,3′-bisdemethylpinoresinol and six new sesquineolignans were isolated besides the known neolignans americanol A, isoamericanol A and isoamericanin A which were found to be the major constituents. A method was developed to distinguish americanol- from isoamericanol-type compounds spectroscopically.

Stereoselective homocoupling of chiral 1-aroylacetyl-2-imidazolidinones by oxidation with Br2

The oxidative coupling of sodium enolates of (4R,5S)-1-aroylacetyl-3,4-dimethyl-5-phenyl-2-imidazolidinones with Br2 as the oxidant affords the R,R-dimers stereoselectively. The R,R-selectivity can be explained by a radical coupling mechanism.