1,5-Dihydroxyanthraquinone

1,5-Dihydroxyanthraquinone
Names
	Other names 1,5-dihydroxy-9,10-anthracenedione, 1,5-dihydroxyanthraquinone, Anthrarufin
Identifiers
CAS Number	117-12-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1881718
ChEBI	CHEBI:37501;
ChEMBL	ChEMBL55761;
ChemSpider	8025;
ECHA InfoCard	100.003.796
EC Number	204-175-6;
Gmelin Reference	144152
PubChem CID	8328;
UNII	KPB60W5S3M;
CompTox Dashboard (EPA)	DTXSID8051594 ;
	InChI InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)8-4-2-6-10(16)12(8)13(7)17/h1-6,15-16H Key: JPICKYUTICNNNJ-UHFFFAOYSA-N;
	SMILES C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C(=CC=C3)O;
Properties
Chemical formula	C14H8O4
Molar mass	240.214 g·mol−1
Appearance	orange solid
Density	1.56 g/cm3
Melting point	280 °C (536 °F; 553 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,5-Dihydroxyanthraquinone is an organic compound with the formula (C₆H₃OH)₂(CO)₂. It is one of several isomers of dihydroxyanthraquinone. An orange solid, it is a component of traditional Chinese medications.^[3] It serves as a chelating ligand for transition metals.^[4]

References

^ Marasinghe, P. A. B.; Gillispie, G. D. (1993). "Structure of 1,5-dihydroxyanthraquinone: A redetermination". Acta Crystallographica Section C Crystal Structure Communications. 49 (1): 113–114. Bibcode:1993AcCrC..49..113M. doi:10.1107/s0108270192004542.
^ "1,5-Dihydroxyanthraquinone". pubchem.ncbi.nlm.nih.gov.
^ Cai, Yi-Zhong; Mei Sun; Jie Xing; Luo, Qiong; Corke, Harold (2006). "Structure–radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants". Life Sciences. 78 (25): 2872–2888. doi:10.1016/j.lfs.2005.11.004. PMID 16325868.
^ Lin, Yue-Jian; Han, Ying-Feng; Jin, Guo-Xin (2012). "Synthesis and Structural characterization of half-sandwich iridium macro-metallacycles containing 1,5-dihydroxy-9,10- anthraquinone ligand". Journal of Organometallic Chemistry. 708–709: 31–36. doi:10.1016/j.jorganchem.2012.02.014.

[1] Marasinghe, P. A. B.; Gillispie, G. D. (1993). "Structure of 1,5-dihydroxyanthraquinone: A redetermination". Acta Crystallographica Section C Crystal Structure Communications. 49 (1): 113–114. Bibcode:1993AcCrC..49..113M. doi:10.1107/s0108270192004542.

[2] "1,5-Dihydroxyanthraquinone". pubchem.ncbi.nlm.nih.gov.

[3] Cai, Yi-Zhong; Mei Sun; Jie Xing; Luo, Qiong; Corke, Harold (2006). "Structure–radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants". Life Sciences. 78 (25): 2872–2888. doi:10.1016/j.lfs.2005.11.004. PMID 16325868.

[4] Lin, Yue-Jian; Han, Ying-Feng; Jin, Guo-Xin (2012). "Synthesis and Structural characterization of half-sandwich iridium macro-metallacycles containing 1,5-dihydroxy-9,10- anthraquinone ligand". Journal of Organometallic Chemistry. 708–709: 31–36. doi:10.1016/j.jorganchem.2012.02.014.

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v t e Types of natural anthraquinones
Dihydroxyanthraquinones	Alizarin Aloe emodin Damnacanthal 1,3-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone 1,8-Dihydroxyanthraquinone Rhein
Trihydroxyanthraquinones	Parietin Emodin 1,2,4-Trihydroxyanthraquinone 1,3,8-Trihydroxyanthraquinone
Tetrahydroxyanthraquinones	quinalizarin rheoemodin
Misc:	Kermesic acid Carminic acid Senna glycosides