1,8-dihydroxyanthraquinone

Structural formula
General
Surname	1,8-dihydroxyanthraquinone
other names	Chrysazine; Danthron; Istizin; 1,8-dihydroxy-9,10-anthraquinone; 1,8-dihydroxy-9,10-anthracenedione;
Molecular formula	C 14 H 8 O 4
Brief description	orange to brown powder
External identifiers / databases
EC number	204-173-5
ECHA InfoCard	100.003.794
PubChem	2950
ChemSpider	2845
DrugBank	DB04816
Wikidata	Q5221244
Drug information
ATC code	A06 AB03
properties
Molar mass	240.21 g mol −1
Physical state	firmly
Melting point	190-193 ° C
solubility	practically insoluble in water ; slightly soluble in ethanol and diethyl ether ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 319-351
	P: 281-305 + 351 + 338
Toxicological data	> 10 mg kg −1 ( LD 50 , mouse , iv ) ; > 7 mg kg −1 ( LD 50 , mouse , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,8-Dihydroxyanthraquinone , also known as chrysazine or danthrone , is an organic compound from the group of anthraquinones (more precisely, the dihydroxyanthraquinones ).

Occurrence

Madder madder ( Rubia tinctorum )

Chrysazin comes in addition to other anthraquinones glycosidically bound in the roots of the dyers madder , and in many Aloearten (especially in real aloe ) as aloe-emodin before.

presentation

Chrysazine can be obtained by photooxidation of dithranol with stimulated oxygen. The following reaction mechanism was demonstrated using the oxygen isotope ¹⁸ O (shown in blue ).

properties

The 1,8-dihydroxyanthraquinone can be detected by mixing ether , magnesium sulfate and ammonia , because the ether phase and the aqueous phase turn red when present.

use

The derivatives and glycosides found in the aloe species have a laxative effect and are therefore used as laxatives.

Biological importance

Chrysazine is classified as a carcinogen in some countries. It does not act as a carcinogen , but only as an enhancer of cancer formation.

Individual evidence

↑ Danthron data sheet at AlfaAesar, accessed on July 24, 2017 ( PDF )(JavaScript required) .

↑ ^a ^b ^c ^d Entry on 1,8-dihydroxyanthraquinone in the GESTIS substance database of the IFA , accessed on January 22, 2018 (JavaScript required)

↑ Entry on Dantron. In: Römpp Online . Georg Thieme Verlag, accessed on June 21, 2018.

↑ ^a ^b Entry on 1,8-dihydroxyanthraquinone in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 13, 2017.

↑ Goverdina CH Derksen, Harm AG Niederländer, Teris A. van Beek: Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection. In: Journal of Chromatography A . 978 (1-2), 2002, pp. 119-127, doi: 10.1016 / S0021-9673 (02) 01412-7 .

↑ Berhanu M. Abegaz, BT Ngadjui, Merhatibeb Bezabih, LK Mdee: Novel natural products from marketed plants of eastern and southern Africa. In: Pure and Applied Chemistry . 71, 1999, doi: 10.1351 / pac199971060919 .

↑ Maher Kammoun, Sonia Miladi, Yassine Ali, Mohamed Damak, Youssef Gargouri, Sofiane Bezzine: In vitro study of the PLA2 inhibition and antioxidant activities of Aloe vera leaf skin extracts. In: Lipids in Health and Disease . 10, 2011, p. 30, doi: 10.1186 / 1476-511X-10-30 .

↑ Müller, K., Mayer, KK and Wiegrebe, Wolfgang: ¹ O ₂ -Oxidation of Dithranol to Chrysazine. In: Archives of Pharmacy . 319, 1986, pp. 1009-1018 urn : nbn: de: bvb: 355-epub-156619

↑ Wolfgang Schneider: About some analytically usable metal verifications (lithium, magnesium, aluminum) with the help of Istizin. In: Archives of Pharmacy . 283, 1950, pp. 248-253, doi: 10.1002 / ardp.19502830405 .

↑ Final community herbal monograph on Aloe barbadensis Miller and on Aloe (various species, mainly Aloe ferox Miller and its hybrids) (PDF; 109 kB) Committee on Herbal Medicines of the European Medicines Agency, October 26, 2006.

^ NTP Report on 1996 Background Document for Danthron Carcinogens. (PDF) Retrieved July 17, 2017 .

[Alfa_Aesar-1] Danthron data sheet at AlfaAesar, accessed on July 24, 2017 ( PDF )(JavaScript required) .

[GESTIS-2] Entry on 1,8-dihydroxyanthraquinone in the GESTIS substance database of the IFA , accessed on January 22, 2018 (JavaScript required)

[Römpp-3] Entry on Dantron. In: Römpp Online . Georg Thieme Verlag, accessed on June 21, 2018.

[ChemIDplus-4] Entry on 1,8-dihydroxyanthraquinone in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 13, 2017.

[Färberkrapp-5] Goverdina CH Derksen, Harm AG Niederländer, Teris A. van Beek: Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection. In: Journal of Chromatography A . 978 (1-2), 2002, pp. 119-127, doi: 10.1016 / S0021-9673 (02) 01412-7 .

[DOI10.1351/pac199971060919-6] Berhanu M. Abegaz, BT Ngadjui, Merhatibeb Bezabih, LK Mdee: Novel natural products from marketed plants of eastern and southern Africa. In: Pure and Applied Chemistry . 71, 1999, doi: 10.1351 / pac199971060919 .

[DOI10.1186/1476-511X-10-30-7] Maher Kammoun, Sonia Miladi, Yassine Ali, Mohamed Damak, Youssef Gargouri, Sofiane Bezzine: In vitro study of the PLA2 inhibition and antioxidant activities of Aloe vera leaf skin extracts. In: Lipids in Health and Disease . 10, 2011, p. 30, doi: 10.1186 / 1476-511X-10-30 .

[Dithranol-8] Müller, K., Mayer, KK and Wiegrebe, Wolfgang: ¹ O ₂ -Oxidation of Dithranol to Chrysazine. In: Archives of Pharmacy . 319, 1986, pp. 1009-1018 urn : nbn: de: bvb: 355-epub-156619

[DOI10.1002/ardp.19502830405-9] Wolfgang Schneider: About some analytically usable metal verifications (lithium, magnesium, aluminum) with the help of Istizin. In: Archives of Pharmacy . 283, 1950, pp. 248-253, doi: 10.1002 / ardp.19502830405 .

[HMPC-10] Final community herbal monograph on Aloe barbadensis Miller and on Aloe (various species, mainly Aloe ferox Miller and its hybrids) (PDF; 109 kB) Committee on Herbal Medicines of the European Medicines Agency, October 26, 2006.

[niehs.nih.gov-11] NTP Report on 1996 Background Document for Danthron Carcinogens. (PDF) Retrieved July 17, 2017 .