78472-08-9

Basic information

• Product Name: PALLASONE B
• Synonyms: Dihydroirisquinone;Irisquinone B; Pallasone B
• CAS NO: 78472-08-9
• Molecular Formula: C₂₄H₄₀O₃
• Molecular Weight: 376.5726
• Product Categories: Anthraquinones, Hydroquinones and Quinones
• Mol File: 78472-08-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PALLASONE B(CAS DataBase Reference)
• NIST Chemistry Reference: PALLASONE B(78472-08-9)
• EPA Substance Registry System: PALLASONE B(78472-08-9)

Safety Data

• Hazardous Substances Data: 78472-08-9(Hazardous Substances Data)

Upstream product

• 134284-28-9 2-heptadecyl-6-methoxyphenol 
• 131248-35-6 heptadec-1-en-3-ol 
• 483355-52-8 1-methoxy-2-(heptadec-1-en-3-yloxy)benzene 
• 483355-53-9 2-(heptadec-2-enyl)-6-methoxyphenol 
• 2765-11-9 n-pentadecanal 

Relevant articles and documents

Ultrasound-assisted Wittig reaction: A short, efficient synthesis of 2-methoxy-6-alkyl-1,4-benzoquinones

A short, efficient synthesis of 2-methoxy-6-alkyl-1,4-benzoquinones is described. Ultrasound-assisted Wittig reaction of alkyltriphenyl phosphonium bromides with o-vanillin in basic aqueous conditions followed by reduction with Na/n-BuOH gave 2-methoxy-6-alkylphenols. Oxidation of 2-methoxy-6-alkylphenols with Fremy's salt produced the title compounds.

Microwave-mediated claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring 1,4-benzoquinones. The first syntheses of verapliquinones A and B and panicein A

The naturally occurring 1,4-benzoquinones 2-methoxy-6-propyl-1,4- benzoquinone (1), 2-methoxy-6-pentyl-1,4-benzoquinone (primin 2), 2-methoxy-6-pentadecyl-1,4-benzoquinone (3), 2-methoxy-6-heptadecyl-l,4- benzoquinone (dihydroirisquinone, pallasone B; 4) were synthesized by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 10, followed by hydrogenation of the side chain alkene, and oxidation to the quinone. The Claisen-based methodology was extended to the first synthesis of the marine benzoquinones verapliquinones A and B (5 and 6), and panicein A (7). Isoarnebifuranone (9) was also synthesized by a similar strategy.

The Claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring benzoquinones including an ansa-bridged derivative related to the ansamycin antibiotics

The naturally occurring benzoquinones primin 1 and pallasone B 2 were synthesised by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 4, followed by hydrogenation of the side chain alkene, and oxidation to the quinon