Quinones

Quinones are a class of organic compounds consisting of a six-carbon cyclic dione structure containing two double-bonds, such as p-benzoquinone, o-benzoquinone. Having the properties of open-chain dicarboxylic ketones, quinones can take part in addition reactions and reduction reactions. But they lack the properties of the aromatic compounds. Quinoid structures and their color are closely related, and therefore most of the quinone compounds are colored substances. Quinones also include naphthoquinone , phenanthrenequinone and anthraquinones in a broad way.

Quinones is a class of compounds comprising quinones and compounds easily converted into structures with characteristics of quinones, as well as compounds closely related with the quinones in biosynthesis, often found in nature as pigment in animals, plants, microbes. The main active ingredients of many important  traditional Chinese herbs such as rhubarb, cassia, senna, comfrey, giant knotweed, Polygonum, aloe vera have quinone compounds.

According to their different chemical structures, quinone compounds can be divided into benzene quinone , naphthalene quinones , anthraquinones and quinones. These quinones transfer electrons in redox reactions. And some have anti-bacterial or anti-tumor activity, such as juglone, 5-Hydroxy-2-Methyl-1,4-Naphthoquinon, lapachone. And some are the main active ingredients of Chinese herbal medicines, such as shikonin and isoalkannin class in puccoon which have the hemostatic, anti-inflammatory, anti-viral and anti-tumor activity.

If there is no phenolic hydroxyl group in the molecule, quinones are nearly colorless. With auxochromes such as phenolic hydroxyl groups, quinones will show a certain color such as yellow, orange, reddish brown, purple and so on. The more auxochromes there are, the deeper the color is. The color of anthracene derivatives ranges mostly from yellow to orange-red. Natural quinones are mostly colored crystals. Benzoquinones and naphthoquinones are found mostly in free form; and anthraquinones exist in binding form as glycosides in traditional Chinese medicine, the most of which are difficult to obtain good crystallinity. Most of free anthracenes and quinone derivatives are sublimable. Small-molecule benzoquinones and naphthoquinones are volatile and distillable along with the water vapor. Free anthracenes and quinone derivatives can be dissolved in methanol, ethanol, ethyl acetate, ethyl ether, benzene, chloroform and other organic solvents, slightly soluble or insoluble in water. After combined into glycosides, with the increased polarity, quinones can be easily dissolved in methanol, ethanol, and soluble in hot water, but slightly soluble in cold water, and almost insoluble in benzene, ether, chloroform and other non-polar organic solvents.

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Structure Chemical Name CAS MF
Anthraquinone Anthraquinone 84-65-1 C14H8O2
Chloranil Chloranil 118-75-2 C6Cl4O2
1,4-Benzoquinone 1,4-Benzoquinone 106-51-4 C6H4O2
2-Bromoanthraquinone 2-Bromoanthraquinone 572-83-8 C14H7BrO2
Quinhydrone Quinhydrone 106-34-3 C12H10O4
2,6-Dibromoanthraquinone 2,6-Dibromoanthraquinone 633-70-5 C14H6Br2O2
1,4-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone 81-64-1 C14H8O4
1,4-Diamino anthraquinone 1,4-Diamino anthraquinone 128-95-0 C14H10N2O2
2-Ethyl anthraquinone 2-Ethyl anthraquinone 84-51-5 C16H12O2
2-AMINOANTHRAQUINONE 2-AMINOANTHRAQUINONE 117-79-3 C14H9NO2
2-Chloroanthraquinone 2-Chloroanthraquinone 131-09-9 C14H7ClO2
NA NA
1-Chloro anthraquinone 1-Chloro anthraquinone 82-44-0 C14H7ClO2
5-IODOISATIN 5-IODOISATIN 20780-76-1 C8H4INO2
1-Hydroxy anthraquinone 1-Hydroxy anthraquinone 129-43-1 C14H8O3
1-Amino anthraquinone 1-Amino anthraquinone 82-45-1 C14H9NO2
1,5-DIAMINOANTHRAQUINONE 1,5-DIAMINOANTHRAQUINONE 129-44-2 C14H10N2O2
2,5-DIBROMO-1,4-BENZOQUINONE 2,5-DIBROMO-1,4-BENZOQUINONE 1633-14-3 C6H2Br2O2
1,4-DICHLOROANTHRAQUINONE 1,4-DICHLOROANTHRAQUINONE 602-25-5 C14H6Cl2O2
TETRAHYDROXY-P-BENZOQUINONE DIHYDRATE TETRAHYDROXY-P-BENZOQUINONE DIHYDRATE 5676-48-2 C6H8O8
3,6-Dibromo-phenanthrenequinone 3,6-Dibromo-phenanthrenequinone 53348-05-3 C14H6Br2O2
METHOXYBENZOQUINONE METHOXYBENZOQUINONE 2880-58-2 C7H6O3
LAPACHOL LAPACHOL 84-79-7 C15H14O3
1,4-ANTHRAQUINONE 1,4-ANTHRAQUINONE 635-12-1 C14H8O2
1-NITROANTHRAQUINONE 1-NITROANTHRAQUINONE 82-34-8 C14H7NO4
2-(1,1-Dimethylpropyl)anthraquinone 2-(1,1-Dimethylpropyl)anthraquinone 32588-54-8 C19H18O2
2-Amylanthraquinone 2-Amylanthraquinone 13936-21-5 C19H18O2
1-HYDROXY-4-NITROANTHRAQUINONE 1-HYDROXY-4-NITROANTHRAQUINONE 81-65-2 C14H7NO5
ACEQUINOCYL ACEQUINOCYL 57960-19-7 C24H32O4
deoxylapachol deoxylapachol 3568-90-9 C15H14O2
Obtusifolin Obtusifolin 477-85-0 C16H12O5
Tetrahydroxyquinone Tetrahydroxyquinone 319-89-1 C6H4O6
1 5-DINITROANTHRAQUINONE  97 1 5-DINITROANTHRAQUINONE 97 82-35-9 C14H6N2O6
1-BROMOANTHRAQUINONE 1-BROMOANTHRAQUINONE 632-83-7 C14H7BrO2
2,7-Diiodophenanthrenequinone 2,7-Diiodophenanthrenequinone 16218-32-9 C14H6I2O2
2-(BROMOMETHYL)ANTHRAQUINONE 2-(BROMOMETHYL)ANTHRAQUINONE 7598-10-9 C15H9BrO2
1,8-DINITROANTHRAQUINONE 1,8-DINITROANTHRAQUINONE 129-39-5 C14H6N2O6
Pyrroloquinoline quinone Pyrroloquinoline quinone 72909-34-3 C14H6N2O8
1,4-DIFLUOROANTHRAQUINONE 1,4-DIFLUOROANTHRAQUINONE 28736-42-7 C14H6F2O2
(1R)-(-)-CAMPHORQUINONE (1R)-(-)-CAMPHORQUINONE 10334-26-6 C10H14O2
2,5-DI-TERT-AMYLBENZOQUINONE 2,5-DI-TERT-AMYLBENZOQUINONE 4584-63-8 C16H24O2
2,3-DIMETHYLANTHRAQUINONE 2,3-DIMETHYLANTHRAQUINONE 6531-35-7 C16H12O2
2,7-Dibromo-9,10-phenanthrenedione 2,7-Dibromo-9,10-phenanthrenedione 84405-44-7 C14H6Br2O2
N-CHLORO-P-BENZOQUINONEIMINE N-CHLORO-P-BENZOQUINONEIMINE 637-61-6 C6H4ClNO
DUROHYDROQUINONE DUROHYDROQUINONE 527-18-4 C10H14O2
D-ALPHA-TOCOPHERYLQUINONE D-ALPHA-TOCOPHERYLQUINONE 7559-04-8 C29H50O3
2-HYDROXYANTHRAQUINONE 2-HYDROXYANTHRAQUINONE 605-32-3 C14H8O3
2,3-Dichloroanthraquinone 2,3-Dichloroanthraquinone 84-45-7 C14H6Cl2O2
Buparvaquone Buparvaquone 88426-33-9 C21H26O3
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