137494-04-3

Basic information

• Product Name: Regiolone
• Synonyms: Regiolone;(4R)-3,4-Dihydro-4,8-dihydroxy-1(2H)-naphthalenone;(4R)-4,8-Dihydroxy-alpha-tetralone;(R)-(-)-Regiolone;1(2H)-Naphthalenone, 3,4-dihydro-4,8-dihydroxy-, (R)-
• CAS NO: 137494-04-3
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.1846
• Mol File: 137494-04-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Regiolone(CAS DataBase Reference)
• NIST Chemistry Reference: Regiolone(137494-04-3)
• EPA Substance Registry System: Regiolone(137494-04-3)

Safety Data

• Hazardous Substances Data: 137494-04-3(Hazardous Substances Data)

Upstream product

• 51114-98-8 isosclerone 
• 6312-53-4 juglone 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 53859-14-6 4,8-dibenzoyl ester-1-tetralone 
• 481-40-3 1,4,5-trihydroxynaphthalene 
• 91368-83-1 5-acetoxy-2,3-dihydro-[1,4]naphthoquinone 
• 77-76-9 2,2-dimethoxy-propane 
• 129240-52-4 preussomerin A 

Downstream Products

• 54712-38-8 (-)-(4S)-4,8-dihydroxy-α-tetralone 
• 88899-02-9 cis-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-one 
• 88899-02-9 2,4,8-trihydroxy-1-tetralone 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 

Relevant articles and documents

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Unprecedented role of hydronaphthoquinone tautomers in biosynthesis

Quinones and hydroquinones are among the most common cellular cofactors, redox mediators, and natural products. Here, we report on the reduction of 2-hydroxynaphthoquinones to the stable 1,4-diketo tautomeric form of hydronaphthoquinones and their further reduction by fungal tetrahydroxynaphthalene reductase. The very high diastereomeric and enantiomeric excess, together with the high yield of cis-3,4-dihydroxy-1-tetralone, exclude an intermediary hydronaphthoquinone. Labeling experiments with NADPH and NADPD corroborated the formation of an unexpected 1,4-diketo tautomeric form of 2-hydroxyhydronaphthoquinone as a stable intermediate. Similar 1,4-diketo tautomers of hydronaphthoquinones were established as products of the NADPH-dependent enzymatic reduction of other 1,4-naphthoquinones, and as substrates for different members of the superfamily of short-chain dehydrogenases. We propose an essential role of hydroquinone diketo tautomers in biosynthesis and detoxification processes.

Asymmetric synthesis of the cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-ones

A short and efficient protocol for the asymmetric synthesis of cis- and trans-3,4-dihydro-2,4,8-trihydroxynaphthalen-1(2H)-one (1 and 2, resp.) is described, with a phthalide annulation as the key step. Introduction of a OH substituent at position 2 was performed by Sharpless dihydroxylation of a silyl enol ether or by means of an N-sulfonyloxaziridine. The absolute configuration of each isomer was determined via Mosherester derivatives. By comparison with previously recorded CD spectra of our natural sample, we established that the natural trans- and cis-isomers from Ceratocystis fimbriata sp. platani were the (-)-(2S,4S)-isomer (-)-2 and the (+)-(2S,4R)-isomer (+)-1, respectively.