7-Chloroemodin
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| Category | Others |
| Catalog number | BBF-05014 |
| CAS | 18521-72-7 |
| Molecular Weight | 304.68 |
| Molecular Formula | C15H9ClO5 |
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Specification
| Synonyms | 2-Chloro-1,3,8-trihydroxy-6-methyl-9,10-anthracenedione; 2-Chloro-1,3,8-trihydroxy-6-methylanthraquinone; 2-Chloroemodin |
| IUPAC Name | 2-chloro-1,3,8-trihydroxy-6-methylanthracene-9,10-dione |
| Canonical SMILES | CC1=CC2=C(C(=C1)O)C(=O)C3=C(C(=C(C=C3C2=O)O)Cl)O |
| InChI | InChI=1S/C15H9ClO5/c1-5-2-6-10(8(17)3-5)14(20)11-7(13(6)19)4-9(18)12(16)15(11)21/h2-4,17-18,21H,1H3 |
| InChI Key | AVSZOSVPTLSHOV-UHFFFAOYSA-N |
Properties
| Boiling Point | 531.6±50.0°C (Predicted) |
| Melting Point | 281-282°C |
| Density | 1.668±0.06 g/cm3 (Predicted) |
Reference Reading
1. Antiviral activities of anthraquinones, bianthrones and hypericin derivatives from lichens
P A Cohen, J B Hudson, G H Towers Experientia. 1996 Feb 15;52(2):180-3. doi: 10.1007/BF01923366.
The antiviral activities of some naturally occurring anthraquinones, bianthrones, and hypericin derivatives were compared by the end-point CPE (viral cytopathic effects) method and plaque assays. Under optimal conditions of exposure to light, hypericin, 7,7'-dichlorohypericin and 5,7-dichloroemodin exhibited strong inhibitory activity against HSV-1 (herpes simplex virus type 1) in both assays. Partial inactivation of the virus was shown by emodin, 7-chloroemodin and 7-chloro-1-O-methylemodin; the bianthrones and other anthraquinones were found to be inactive. Antiviral activity appeared to be positively correlated with increasing substitution of chlorine in the anthraquinone structure. In the absence of light, only hypericin and 7,7'-dichlorohypericin displayed detectable activity.
2. Chemodiversity and Anti-Leukemia Effect of Metabolites from Penicillium setosum CMLD 18
Ana Calheiros de Carvalho, Cauê Santos Lima, Heron Fernandes Vieira Torquato, André Tarsis Domiciano, Sebastião da Cruz Silva, Lucas Magalhães de Abreu, Miriam Uemi, Edgar Julian Paredes-Gamero, Paulo Cezar Vieira, Thiago André Moura Veiga, Lívia Soman de Medeiros Metabolites. 2022 Dec 23;13(1):23. doi: 10.3390/metabo13010023.
Penicillium setosum represents a Penicillium species recently described, with little up-to-date information about its metabolic and biological potential. Due to this scenario, we performed chemical and biological studies of P. setosum CMLD18, a strain isolated from Swinglea glutinosa (Rutaceae). HRMS-MS guided dereplication strategies and anti-leukemia assays conducted the isolation and characterization of six compounds after several chromatographic procedures: 2-chloroemodic acid (2), 2-chloro-1,3,8-trihydroxy-6- (hydroxymethyl)-anthraquinone (7), 7-chloroemodin (8), bisdethiobis(methylthio)acetylaranotine (9), fellutanine C (10), and 4-methyl-5,6-diihydro-2H-pyran-2-one (15). From the assayed metabolites, (10) induced cellular death against Kasumi-1, a human leukemia cell line, as well as good selectivity for it, displaying promising cytotoxic activity. Here, the correct NMR signal assignments for (9) are also described. Therefore, this work highlights more detailed knowledge about the P. setosum chemical profile as well as its biological potential, offering prospects for obtaining natural products with anti-leukemia capabilities.
3. Two-dimensional TLC separation and mass spectrometric identification of anthraquinones isolated from the fungus Dermocybe sanguinea
R Räisänen, H Björk, P H Hynninen Z Naturforsch C J Biosci. 2000 Mar-Apr;55(3-4):195-202. doi: 10.1515/znc-2000-3-410.
A new two-dimensional TLC technique was developed to separate substituted anthraquinones on silica plates using n-pentanol-pyridine-methanol (6:4:3, v/v/v) and toluene-ethyl acetate-ethanol-formic acid (10:8:1:2, v/v/v/v) as eluents. The good separation power of the new technique was demonstrated by applying it to the analysis of complex anthraquinone mixtures isolated from the Scandinavian Dermocybe sanguinea. Emodin, physcion, endocrocin, dermolutein, dermorubin, 5-chlorodermorubin, emodin-1-beta-D-glucopyranoside, dermocybin-1-beta-D-glucopyranoside and dermocybin, and five new, earlier in D. sanguinea unidentified compounds, 7-chloroemodin, 5,7-dichloroemodin, 5,7-dichloroendocrocin, 4-hydroxyaustrocorticone and austrocorticone, were separated and identified on the basis of Rf-values, UV/Vis spectra and mass spectra.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
