111407-29-5

Basic information

• Product Name: xanthoxylol
• Synonyms: xanthoxylol
• CAS NO: 111407-29-5
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.37
• Mol File: 111407-29-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 527.3°Cat760mmHg
• Flash Point: 272.7°C
• Appearance: /
• Density: 1.334g/cm³
• Vapor Pressure: 9.8E-12mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: xanthoxylol(CAS DataBase Reference)
• NIST Chemistry Reference: xanthoxylol(111407-29-5)
• EPA Substance Registry System: xanthoxylol(111407-29-5)

Safety Data

• Hazardous Substances Data: 111407-29-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H20O6/c1-22-17-6-11(2-4-15(17)21)19-13-8-24-20(14(13)9-23-19)12-3-5-16-18(7-12)26-10-25-16/h2-7,13-14,19-21H,8-10H2,1H3

Upstream product

• 62848-90-2 trans-4-carboxy-5-(3,4-methylenedioxyphenyl)dihydrofuran-2(3H)-one 
• 52200-05-2 4-methanesulfonyloxy-3-methoxybenzaldehyde 
• 651779-93-0 (1R,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane 
• 105602-54-8 (4S,5R)-5-Benzo[1,3]dioxol-5-yl-4-[(4-benzyloxy-3-methoxy-phenyl)-methoxy-methoxymethyl]-dihydro-furan-2-one 
• 16108-37-5 trans-4-hydroxymethyl-5-(3,4-methylenedioxyphenyl)-dihydrofuran-2(3H)-one 
• 120-57-0 piperonal 
• 105602-53-7 benzyl 2-epistyraxin 
• 105602-52-6 (R)-Benzo[1,3]dioxol-5-yl-[(3S,4S,5S)-5-(4-benzyloxy-3-methoxy-phenyl)-4-hydroxymethyl-tetrahydro-furan-3-yl]-methanol 
• 651779-88-3 (4R,5S)-5-(4-methanesulfonyloxy-3-methoxy)phenyl-4-{[(3,4-methylenedioxybenzyl)oxy]methyl}-3-acetyltetrahydro-2-furanone 
• 651779-89-4 (4R,5S)-5-(4-methanesulfonyloxy-3-methoxy)phenyl-3-diazo-4-{[(3,4-methylenedioxybenzyl)oxy]methyl}tetrahydro-2-furanone 
• 651779-87-2 (1R,4S,5S)-1-acetyl-4-(4-methanesulfonyloxy-3-methoxyphenyl)-3-oxabicyclo[3.1.0]hexan-2-one 
• 651779-86-1 (1S)-1-(4-methanesulfonyloxy-3-methoxyphenyl)allyl acetoacetate 
• 651779-84-9 1-(4-methanesulfonyloxy-3-methoxyphenyl)prop-2-en-1-ol 
• 105602-51-5 (+/-)-benzylpluviatilol 

Downstream Products

• 28115-69-7 (1R,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(3,4-dimethoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane 

Related news

Revised structures for pluviatilol, methyl pluviatilol and xanthoxylol (cas 111407-29-5) : General methods for the assignment of stereochemistry to 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans08/30/2019

The isolation and characterisation of methyl piperitol, (+)-epieudesmin and (+)-episesamin from the stem bark of Zanthoxylum acanthapodium is reported. The 1H and 13C NMR spectra are correlated with those of other known lignans and it is shown that 13C NMR shifts can be used to assign unambiguou...detailed

Relevant articles and documents

A Versatile Stereoselective Synthesis of endo,exo-Furofuranones: Application to the Enantioselective Synthesis of Furofuran Lignans

A new stereoselective route to endo,exo-2,6-diarylfurofuranones has been developed using Mn(III)-mediated intramolecular cyclopropanation and C-H insertion reactions as key C-C bond-forming steps. Mn(III)-mediated oxidative cyclization of acetoacetate derivative 11 afforded 1-acetyl-4-aryl-3-oxabicyclo[3.1.0]hexan-2-one (12) with excellent diastereocontrol (d.r. 22:1). Subsequent Lewis acid-catalyzed opening of the activated cyclopropane ring present in 12 with benzylic alcohols then gave α-acetyl-γ-butyrolactones 16 and 18-20, which reacted efficiently with in situ-generated TfN3 to secure the key α-diazo-γ -butyrolactones 22-25. Highly stereoselective rhodium-catalyzed C-H insertion reactions of diazolactones 22-25 completed the synthesis of endo,exo-2,6-diarylfurofuranones 26-29 in overall yields ranging from 41 to 48% from 1-phenylallyl alcohol (±)-10. The approach developed for the furofuranones 26-29 was then applied to the asymmetric syntheses of four furofuran lignans, (+)-xanthoxylol (1), (+)-methylxanthoxylol (2), (+)-epipinoresinol (3), and (+)-epieudesmin (4), starting from enantiomerically enriched 1-arylallyl alcohol (S)-31.

Synthetic methods for (Exo,Exo)- and (Exo-,Endo)-2,6-diarylbicyclo[3:3:0]octane lignans: Syntheses of (±)-aptosimon, (±)-styraxin, (±)-asarinin, and (±)-pluviatilol

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