86690-14-4

Basic information

• Product Name: halenaquinone
• Synonyms: halenaquinone;(S)-12bβ-Methyl-1H-5-oxabenzo[k]acephenanthrylene-3,6,8,11(2H,12bH)-tetrone
• CAS NO: 86690-14-4
• Molecular Formula: C₂₀H₁₂O₅
• Molecular Weight: 332.30628
• Mol File: 86690-14-4.mol

Chemical Properties

• Boiling Point: 601.2°C at 760 mmHg
• Flash Point: 302.7°C
• Appearance: /
• Density: 1.501g/cm³
• Vapor Pressure: 2.06E-14mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: halenaquinone(CAS DataBase Reference)
• NIST Chemistry Reference: halenaquinone(86690-14-4)
• EPA Substance Registry System: halenaquinone(86690-14-4)

Safety Data

• Hazardous Substances Data: 86690-14-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H12O5/c1-20-5-4-16(23)12-8-25-19(17(12)20)18(24)11-6-9-10(7-13(11)20)15(22)3-2-14(9)21/h2-3,6-8H,4-5H2,1H3/t20-/m0/s1

Upstream product

• 96603-02-0 halenaquinol 
• 99463-22-6 (+)-Halenaquinol dimethyl ether 
• 117556-90-8 (8aR)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione 1-ethylene ketal 
• 117556-91-9 (4aR,8aR)-3,4,4a,7,8,8a-hexahydro-8a-methyl-6-(trimethylsiloxy)-1(2H)-naphthalenone 1-ethylene acetal 
• 117439-25-5 (4aS,7S,8S,8aR)-(+)-4a,5,6,7,8,8a-hexahydro-7-hydroxy-8-(hydroxymethyl)-4a-methyl-2-naphthalenone acetonide 
• 117439-24-4 (1S,2S,4aS,8aR)-(-)-1,2,3,4,4a,7,8,8a-octahydro-1-(hydroxymethyl)-4a-methyl-2-naphthalenol acetonide 
• 117439-22-2 (4aR,5S,6S,8aR)-(+)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5-(hydroxymethyl)-8a-methyl-1-(2H)-naphthalenone 
• 117439-21-1 (4aR,5S,6S,8aR)-(+)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5-(hydroxymethyl)-8a-methyl-1-(2H)-naphthalenone 1-ethylene acetal 
• 117439-23-3 (1S,2S,4aS,8aR)-(-)-1,2,3,4,4a,7,8,8a-octahydro-1-(hydroxymethyl)-4a-methyl-2-naphthalenol 
• 117439-20-0 (4aR,5S,8aR)-3,4,4a,5,8,8a-hexahydro-5-(hydroxymethyl)-8a-methyl-1,6-(2H,7H)-naphthalenedione 1-ethylene acetal 
• 179470-04-3 (S)-2-Hydroxy-3-iodo-5,8-dimethoxy-4-methyl-4-(2-{2-[(triisopropylsilanyl)-ethynyl]-[1,3]dioxan-2-yl}-ethyl)-4H-anthracen-1-one 
• 179470-03-2 (R)-2-Hydroxy-5,8-dimethoxy-4-methyl-4-(2-{2-[(triisopropylsilanyl)-ethynyl]-[1,3]dioxan-2-yl}-ethyl)-4H-anthracen-1-one 
• 179470-05-4 (S)-2-Hydroxy-3-iodo-5,8-dimethoxy-4-methyl-4-(3-oxo-5-triisopropylsilanyl-pent-4-ynyl)-4H-anthracen-1-one 
• 179470-06-5 (S)-8,11-Dimethoxy-12b-methyl-4-triisopropylsilanyl-1,12b-dihydro-2H-5-oxa-benzo[k]acephenanthrylene-3,6-dione 

Downstream Products

• 96603-02-0 halenaquinol 
• 1276044-65-5 C₂₈H₂₃NO₅ 

Relevant articles and documents

Synthesis of biotinylated xestoquinone that retains inhibitory activity against Ca2+ ATPase of skeletal muscle myosin

Xestoquinone isolated from a marine sponge binds to skeletal muscle myosin and inhibits its Ca2+ ATPase activity. In this study, we first examined xestoquinone and its analogues to assess the relationships between structure and myosin Ca2+ ATPase inhibitory activity. On the basis of the resultant data, we then designed a biotinylated xestoquinone analogue. Xestoquinone and its analogues were derived from extracts of the marine sponge Xestospongia sapra. Four xestoquinone analogues with a quinone structure significantly inhibited Ca2+ ATPase activity. In contrast, four xestoquinone analogues in which the quinone structure was converted to a quinol dimethyl ether did not inhibit Ca2+ ATPase activity. This suggests that the quinone moiety is essential for inhibitory activity. Then, we synthesized a biotinylated xestoquinone in which a biotin tag was introduced to a site far from the quinone moiety, and this molecule exhibited stronger inhibitory activity than that of xestoquinone. This biotinylated xestoquinone could be useful as a probe in studies of the xestoquinone-myosin binding mode.

Catalytic asymmetric synthesis of halenaquinone and halenaquinol

A catalytic asymmetric synthesis of halenaquinone (1) and halenaquinol (2) has been achieved using an asymmetric Heck reaction or a cascade Suzuki cross-coupling and an asymmetric Heck reaction as a key step. This synthesis also features the one-pot construction of a unique pentacyclic ring system from a tricyclic system using palladium chemistry. Moreover, the use of Ph3As as an achiral ligand has been found to enhance both the cascade Suzuki cross-coupling and also the Heck reaction to a synthetically useful extent.

HALENAQUINOL AND HALENAQUINOL SULFATE, PENTACYCLIC HYDROQUINONES FROM THE OKINAWAN MARINE SPONGE XESTOSPONGIA SAPRA

Two new pentacyclic hydroquinones named halenaquinol (1) and halenaquinol sulfate (2) were isolated from the Okinawan marine sponge Xestospongia sapra and their structures were elucidated on the basis of chemical and physicochemical evidence which included a quantitative photo-oxidative conversion of 1 to halenaquinone (3).KEYWORDS - halenaquinol; halenaquinol sulfate; hydroquinone containing pentacyclic acetogenin; marine sponge; Xestospongia sapra; hydroquinone photo-oxidation