Hydroxyhydroquinone

Uses. Hydroxyhydroquinone has been used in hair and mordant dyes, for healing plant wounds, and in corrosion inhibitors and adhesives. 

Hydroxyhydroquinone and pyrogaHol can be used for lining reactors for vinyl chloride suspension polymerization to prevent formation of polymer deposits on the reactor walls (98). Hydroxyhydroquinone and certain of its derivatives are useful as auxiUary developers for silver haUde emulsions in photographic material their action is based on the dye diffusion-transfer process. The transferred picture has good contrast and stain-free highlights (99). 5-Acylhydroxyhydroquinones are useful as stabilizer components for poly(alkylene oxide)s (100). 

Cinnamyl—sesamol ethers, eg (35), are useful as insect chemosterilants (111). 3,4-Methylenedioxyphenyl-3-halo-2-propynyl ethers (36, X = halogen) are synergists for carbamate insecticides (112). HaloaLkyl or haloalkenyl ethers, eg (37), show acaricidal and insect juvenile hormone activity (113). The first total synthesis of gibbereUic acid was from 2-methoxy-6-aLkoxyethyl-l,4-benzoquinone, a derivative of hydroxyhydroquinone (114). 

Brune A, S Schnell, B Schink (1992) Sequential transhydroxylations converting hydroxyhydroquinone to phloroglucinol in the strictly anaerobic, fermentative bacterium. Pelobacter massiliensis. Appl Environ Microbiol 58 1861-1868. 

Reichenbecher WW, B Schink (1997) Desulfovibrio inopinatus sp nov, a new sulfate-reducing bacterium that degrades hydroxyhydroquinone (1,2,4-trihydroxybenzene). Arch Microbiol 168 338-344. 

Titanium dioxide suspended in an aqueous solution and irradiated with UV light (A. = 365 nm) converted chlorobenzene to carbon dioxide at a significant rate (Matthews, 1986). Products identified as intermediates in this reaction include three monochlorophenols, chlorohydroquinone, and hydroxyhydroquinone (Kawaguchi and Furuya, 1990). 

Hydroxyhydroquinone, see Parathion Hydroqninone monomethyl ether. Acrylamide,... 

CASRN 108-43-0 molecular formula CeHsClO FW 128.56 Photolytic. Irradiation of an aqueous solution containing 3-chlorophenol and titanium dioxide with UV light (X >340 nm) resulted in the formation of chlorohydroquinone then to hydroxyhydroquinone. Identification of compounds from the oxidation of hydroxyhydroquinone to carbon dioxide were not identified because of the low concentrations (D Oliveira et al, 1990). 

T. Kato, and K. Kikugawa. Identification of hydroxyhydroquinone in coffee as a generator of reactive oxygen spe- CA093 cies that break DNA single strands. 

Yamaguchi, T., Chikama, A., Mori, K., Watanabe, T., Shioya, Y, Katsuragi, Y, Tokimitsu, I. (2007). Hydroxyhydroquinone-free coffee A double-blind, randomized controlled dose-response study of blood pressure. Nutr. Metab. Cardiovasc. Dis. 

Hydroxyhydroquinone (24) forms colorless plates from diethyl ether when freshly prepared. It occurs in many plants and trees in the form of ethers, quinonoid pigments, coumarin derivatives, and complex compounds. Sponges from the coastal waters of Florida have been found to contain small amounts of 1,2,4-trihydroxybenzene and traces of 2,2, 4,4, 6,6 -hexahydroxybiplienyl (25) (78). The benzenetriol has also been isolated from tobacco leaves and tar from tobacco smoke (79). Hydroxyhydroquinone has strong reducing properties. Applications have been suggested in the synthesis of agricultural... 

Properties. Hydroxyhydroquinone forms platelets or prisms (mp 140.5°C). The compound is easily soluble in water, ethanol, diethyl ether, and ethyl acetate and is very sparingly soluble in chloroform, carbon disulfide, benzene, and ligroin. 

Synthesis. Hydroxyhydroquinone is not produced on a large scale, but many uses for it are being developed. The most convenient preparation of hydroxyhydroquinone is the reaction of -benzoquinone with acetic anhydride in the presence of sulfuric acid or phosphoric acid. The resultant triacetate (29) can be hydrolyzed to hydroxyhydroquinone (86). 

Analysis. Dilute aqueous solutions of hydroxyhydroquinone turn blue-green temporarily when mixed with ferric chloride. The solutions darken upon addition of small amounts, and turn red with additions of larger amounts of sodium carbonate. Derivatives used for identification are the picrate, which forms orange-red needles (mp of 96°C), and the triacetate (mp 96—97°C). Thin-layer chromatography and liquid chromatography are well suited for the qualitative and quantitative estimation of hydroxyhydroquinone (93,94). 

Methylesculetol-6,7-dinicotinate (32) is useful as an antiinflammatory and vasodilator oflow toxicity (101). The synthesis of asarone [5555-15-1] (2,4,5-trimethoxy-l-propenylbenzene), which is used as a tranquilizer, has been patented (102). It occurs in calamus root, Acorns calamus L.y and is a chemosterilant for insects (103). 6,7-Dihydroxycoumarin-4-methylsulfonic acid and its salts are useful in the treatment of capillary permeability and fragility and for protecting oxidizable metabolites and drugs against biooxidation (104). Certain chromones derived from hydroxyhydroquinone, eg (33), and its salts, esters, and amides are valuable in the prophylactic treatment of asthma (105) (see Antiasthmatic agents). 2-Methoxy-6-multiprenyl-l,4-benzoquinones are intermediates in the microbiological synthesis of coenzyme Q compounds (106). 

The hydroxyhydroquinone triacetate keeps quite satisfactorily in an atmosphere of carbon dioxide. 

The method described above is essentially the same as that of Thiele,1 which has been patented by F. Bayer and Company.2 Hydroxyhydroquinone triacetate has also been obtained by acetylating hydroxyhydroquinone formed by the alkali fusion of hydroquinone.3... 

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