26430-30-8

Basic information

• Product Name: Carpanone
• Synonyms: (14aR)-7,8,8aβ,14bβ-Tetrahydro-7α,8β-dimethyl-5H-benzo[kl]bis[1,3]dioxolo[4,5-b:4',5'-g]xanthen-5-one;Carpanone
• CAS NO: 26430-30-8
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.35332
• Mol File: 26430-30-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 531.3°Cat760mmHg
• Flash Point: 235.9°C
• Appearance: /
• Density: 1.47g/cm³
• CAS DataBase Reference: Carpanone(CAS DataBase Reference)
• NIST Chemistry Reference: Carpanone(26430-30-8)
• EPA Substance Registry System: Carpanone(26430-30-8)

Safety Data

• Hazardous Substances Data: 26430-30-8(Hazardous Substances Data)

Upstream product

• 19202-23-4 5-hydroxy-6-(2-propenyl)-1,3-benzodioxole 
• 19202-22-3 O-allyl-sesamol 
• 34587-60-5 2-(trans-1-propenyl)-4,5-(methylenedioxy)phenol 
• 533-31-3 Sesamol 
• 67-56-1 methanol 

Relevant articles and documents

Oxidative dimerization of (E)- and (Z)-2-propenylsesamol with O2 in the presence and absence of laccases and other catalysts: Selective formation of carpanones and benzopyrans under different reaction conditions

The oxidative dimerization of 2-propenylsesamol to carpanone with O 2 as the oxidant, which probably proceeds as a domino phenol oxidation/anti-β,β-radical coupling/intramolecular hetero Diels-Alder reaction, can be efficiently catalyzed by laccases. Experiments with laccases and other catalysts like a Co(salen) type catalyst and PdCl2 clearly demonstrate that the diastereoselectivity of the carpanone formation does not depend on the catalyst but on the double-bond geometry of the substrate. With (E)-2-propenylsesamol as the substrate, carpanone and a so far unknown carpanone diastereoisomer are formed in a 9:1 ratio. When (Z)-2-propenylsesamol is used as starting material, carpanone is accompanied by two carpanone diastereoisomers unknown so far in a 5:1:4 ratio. All three carpanone diastereoisomers have been separated by HPLC, and their structures have been elucidated unambiguously by NMR spectroscopy, DFT calculations, and spin work analysis. When the oxidation of 2-propenylsesamol with O2 is performed in the absence of any catalyst two diastereoisomeric benzopyrans are formed, probably as the result of a domino oxidation/intermolecular hetero Diels-Alder reaction. Under these conditions, carpanone is formed in trace amounts only.

ANODIC OXIDATION OF 2-PROPENYLPHENOLS

Anodic oxidation of 2-propenylphenols in MeOH was carried out under various conditions, using an undivided cell, to afford several oxidation products including the corresponding asatone-, carpanone-, arylpropanoid-, and austrobailignan-type compounds.Among them, the carpanone-type neolignans can be produced via the corresponding bis-o-quinonemethides.