Type of compounds
For the parent molecule
9,10-anthraquinone
, see
anthraquinone
Structure proposed for the pigment carmine.
Anthraquinones
(also known as
anthraquinonoids
) are a class of naturally occurring phenolic compounds based on the
9,10-anthraquinone
skeleton. They are widely used industrially and occur naturally.
The name "anthraquinone" was first used by German chemists
Carl Graebe
and
Carl Theodore Liebermann
in a 1868 publication describing the
chemical synthesis
of the red dye
alizarin
from
anthracene
, a component of
coal tar
. This discovery led to the
industrial
production of alizarin and the impetus for further research on anthraquinone chemistry.
[1]
Occurrence in plants
[
edit
]
The yellow color of certain lichens, particularly in the family
Teloschistaceae
(here
Variospora thallincola
), is due to the presence of anthraquinones.
[2]
Natural
pigments
that are derivatives of anthraquinone are found, inter alia, in aloe latex,
senna
,
rhubarb
, and
cascara buckthorn
,
fungi
,
lichens
, and some
insects
. A
type II polyketide synthase
is responsible for anthraquinone biosynthesis in the bacterium
Photorhabdus luminescens
.
[3]
Chorismate
, formed by
isochorismate synthase
in the shikimate pathway, is a precursor of anthraquinones in
Morinda citrifolia
.
[4]
Tests for anthraquinones in natural extracts have been established.
[5]
Applications
[
edit
]
In the production of hydrogen peroxide
[
edit
]
A large industrial application of anthraquinones is for the production of
hydrogen peroxide
.
2-Ethyl-9,10-anthraquinone
or a related alkyl derivative is used, rather than anthraquinone itself.
[7]
Catalytic cycle
for the
anthraquinone process
to produce hydrogen peroxide.
Millions of tons of hydrogen peroxide are manufactured by the
anthraquinone process
.
[8]
Pulping
[
edit
]
Sodium 2-anthraquinonesulfonate
(AMS) is a water-soluble anthraquinone derivative that was the first anthraquinone derivative discovered to have a catalytic effect in the alkaline pulping processes.
[9]
Dyestuff precursor
[
edit
]
The 9,10-anthraquinone skeleton occurs in many dyes, such as
alizarin
.
[10]
Important derivatives of 9,10-anthraquinone are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and the dinitroanthraquinone.
[11]
Selection of
anthraquinone dyes
. From the left: C.I.Acid Blue 43 an "acid dye" for wool (also called "Acilan Saphirol SE"), C.I. Vat Violet 1, which is applied by transfer printing using sublimation, a blue colorant commonly used in gasoline, and C.I.
Disperse Red 60
.
Medicine
[
edit
]
Derivatives of 9,10-anthraquinone include drugs such as the anthracenediones and the
anthracycline
family of
chemotherapy
drugs. The latter drugs are derived from the bacterium
Streptomyces peucetius
, discovered in a soil sample near the
Adriatic Sea
. Drugs in the anthraquinone family include the prototypical
daunorubicin
,
doxorubicin
,
mitoxantrone
,
losoxantrone
, and
pixantrone
. Most of these drugs, with the notable exception of pixantrone, are extremely cardiotoxic, causing irreversible
cardiomyopathy
, which can limit their practical usefulness in
cancer
treatment.
[11]
The anthracenediones also include
Dantron
,
emodin
, and
aloe emodin
, and some of the
senna glycosides
have
laxative
effects. Prolonged use and
abuse
leads to
melanosis coli
.
[13]
[14]
Flow batteries
[
edit
]
Soluble anthraquinones such as 9,10-anthraquinone-2,7-disulfonic acid are used as reactants in
redox flow batteries
, which provide electrical energy storage.
[15]
References
[
edit
]
- ^
Phillips, Max (1929). "The chemistry of anthraquinone".
Chemical Reviews
.
6
(1): 157?174.
doi
:
10.1021/cr60021a007
.
- ^
Llewellyn, Theo; Nowell, Reuben W.; Aptroot, Andre; Temina, Marina; Prescott, Thomas A.K.; Barraclough, Timothy G.; Gaya, Ester (2023).
"Metagenomics shines light on the evolution of "sunscreen" pigment metabolism in the Teloschistales (lichen-forming Ascomycota)"
.
Genome Biology and Evolution
.
15
(2): evad002.
doi
:
10.1093/gbe/evad002
.
PMC
9907504
.
PMID
36634008
.
- ^
Brachmann, AO; Joyce, SA; Jenke-Kodama, H; Schwar, G; Clarke, DJ; Bode, HB (2007). "A type II polyketide synthase is responsible for anthraquinone biosynthesis in
Photorhabdus luminescens
".
ChemBioChem
.
8
(14): 1721?8.
doi
:
10.1002/cbic.200700300
.
PMID
17722122
.
- ^
Stalman, M; Koskamp, AM; Luderer, R; Vernooy, JH; Wind, JC; Wullems, GJ; Croes, AF (2003). "Regulation of anthraquinone biosynthesis in cell cultures of
Morinda citrifolia
".
Journal of Plant Physiology
.
160
(6): 607?14.
doi
:
10.1078/0176-1617-00773
.
PMID
12872482
.
- ^
Akinjogunla OJ, Yah CS, Eghafona NO, Ogbemudia FO (2010). "Antibacterial activity of leave extracts of
Nymphaea lotus
(Nymphaeaceae) on Methicillin resistant
Staphylococcus aureus
(MRSA) and Vancomycin resistant
Staphylococcus aureus
(VRSA) isolated from clinical samples".
Annals of Biological Research
.
1
(2): 174?184.
- ^
Dapson, R. W.; Frank, M.; Penney, D. P.; Kiernan, J. A. (2007). "Revised procedures for the certification of carmine (C.I. 75470, Natural red 4) as a biological stain".
Biotechnic & Histochemistry
.
82
(1): 13?15.
doi
:
10.1080/10520290701207364
.
PMID
17510809
.
- ^
Goor, G.; Glenneberg, J.; Jacobi, S. (2007). "Hydrogen Peroxide".
Ullmann's Encyclopedia of Industrial Chemistry
. Weinheim: Wiley-VCH.
doi
:
10.1002/14356007.a13_443.pub2
.
ISBN
978-3527306732
.
- ^
Campos-Martin, Jose M.; Blanco-Brieva, Gema; Fierro, Jose L. G. (2006). "Hydrogen Peroxide Synthesis: An Outlook beyond the Anthraquinone Process".
Angewandte Chemie International Edition
.
45
(42): 6962?6984.
doi
:
10.1002/anie.200503779
.
PMID
17039551
.
- ^
"Anthraquinone / Alkali Pulping - A Literature Review"
(PDF)
.
Project 3370
. Appleton, Wisconsin: The Institute of Paper Chemistry. 1978-07-05.
- ^
Bien, H.-S.; Stawitz, J.; Wunderlich, K. (2005). "Anthraquinone Dyes and Intermediates".
Ullmann's Encyclopedia of Industrial Chemistry
. Weinheim: Wiley-VCH.
doi
:
10.1002/14356007.a02_355
.
ISBN
978-3527306732
.
- ^
a
b
Vogel, A. "Anthraquinone".
Ullmann's Encyclopedia of Industrial Chemistry
. Weinheim: Wiley-VCH.
doi
:
10.1002/14356007.a02_347
.
ISBN
978-3527306732
.
- ^
Panigrahi, G.K.; Suthar, M.K.; Verma, N.; Asthana, S.; Tripathi, A.; Gupta, S.K.; Saxena, J. K.; Raisuddin, S.; Das, M. (2015). "Investigation of the interaction of anthraquinones of
Cassia occidentalis
seeds with bovine serum albumin by molecular docking and spectroscopic analysis: Correlation to their in vitro cytotoxic potential".
Food Research International
.
77
: 368?377.
doi
:
10.1016/j.foodres.2015.08.022
.
- ^
Muller-Lissner, S. A. (1993). "Adverse Effects of Laxatives: Fact and Fiction".
Pharmacology
.
47
(Suppl 1): 138?145.
doi
:
10.1159/000139853
.
PMID
8234421
.
- ^
Moriarty, K. J.; Silk, D. B. (1988). "Laxative Abuse".
Digestive Diseases
.
6
(1): 15?29.
doi
:
10.1159/000171181
.
PMID
3280173
.
- ^
Fontmorin, Jean-Marie; Guiheneuf, Solene; Godet-Bar, Thibault; Floner, Didier; Geneste, Florence (2022). "How anthraquinones can enable aqueous organic redox flow batteries to meet the needs of industrialization".
Current Opinion in Colloid & Interface Science
.
61
: 101624.
doi
:
10.1016/j.cocis.2022.101624
.