chloroatranorin
{{Chembox
| ImageFile = Chloroatranorin.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = (3-Hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 5-chloro-3-formyl-2,4-dihydroxy-6-methylbenzoate
| OtherNames = 5-Chloroatranorin
| Section1 = {{Chembox Identifiers
| CASNo = 479-16-3
| ChEBI = 144138
| ChemSpiderID = 61379
| PubChem = 68065
| UNII = 433PEB1G7C
| SMILES = CC1=CC(=C(C(=C1C(=O)OC)O)C)OC(=O)C2=C(C(=C(C(=C2O)C=O)O)Cl)C
| InChI = 1S/C19H17ClO8/c1-7-5-11(8(2)15(22)12(7)18(25)27-4)28-19(26)13-9(3)14(20)17(24)10(6-21)16(13)23/h5-6,22-24H,1-4H3
| InChIKey = ABZLZZCDSLOCNF-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C = 19 | H = 17 | Cl = 1 | O = 8
| Appearance =
| Density =
| MeltingPtC = 208-210
| BoilingPt =
| Solubility =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
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Chloroatranorin is a chemical compound with the molecular formula {{chem2|C19H17ClO8}}. It is a secondary metabolite produced by a variety of lichens and is a member of the depside class of compounds. It was first isolated from the oakmoss Evernia prunastri and characterized in 1934.{{cite journal| title = Constituents of lichens. IV. Chloroatranorin | author = Pfau, Alexander S. | journal = Helvetica Chimica Acta | date = 1934 | volume = 17 | pages = 1319–1328 }} It is the most common chlorine-containing depside in lichens, and has been identified in dozens of lichen species.{{cite journal |last1=Dembitsky |first1=Valery M. |last2=Tolstikov |first2=Genrich A. |year=2003 |title=Halogenated phenol compounds in lichens and fungi |journal=Chemistry for Sustainable Development |volume=11 |pages=557–565 |url=https://www.sibran.ru/upload/iblock/9fb/halogenated_phenol_compounds_in_lichens_and_fungi.pdf}}
It is a chlorinated derivative of atranorin and the two are frequently found together in the same source. Ramault and colleagues described an improved method to separate the two compounds using thin-layer chromatography.{{cite journal | doi = 10.1016/S0021-9673(00)88011-5 | title = Separation of mixtures of atranorin and chloroatranorin by thin-layer chromatography | date = 1978 | last1 = Ramaut | first1 = J.L. | last2 = Brouers | first2 = M. | last3 = Serusiaux | first3 = E. | last4 = Corvisier | first4 = M. | journal = Journal of Chromatography A | volume = 155 | issue = 2 | pages = 450–453 | hdl = 2268/174503 | hdl-access = free }}
Properties
Chloroatranorin is a member of the class of chemical compounds called depsides. Its IUPAC name is (3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 5-chloro-3-formyl-2,4-dihydroxy-6-methylbenzoate. The absorbance maxima (λmax) in the ultraviolet spectrum (in methanol solution) are 213, 252, and 282 nm. Its peaks in the infrared spectrum occur at 710, 764, 790, 810, 850, 904, 942, 992, 1030, 1080, 1115, 1160, 1180, 1270, 1285, 1360, 1385, 1408, 1445, 1582, 1650, 3000, and 3500 cm−1. Chloroatranorin's molecular formula is C19H17ClO8; it has a molecular mass of 408.78 grams per mole. In its purified crystalline form, its melting point is {{convert|208|–|208.5|C|F}}.{{cite book |last=Huneck |first=Siegfried |title=Identification of Lichen Substances |publisher=Springer Berlin Heidelberg |publication-place=Berlin, Heidelberg |year=1996 |isbn=978-3-642-85245-9 |oclc=851387266 |page=242}}
Chloroatranorin has been studied for its potential antioxidant, antimicrobial, and anticancer properties.{{cite journal | doi = 10.1016/j.fct.2012.11.034| title = Evernia prunastri and Pseudoevernia furfuraceae lichens and their major metabolites as antioxidant, antimicrobial and anticancer agents| date = 2013| last1 = Kosanić| first1 = Marijana| last2 = Manojlović| first2 = Nedeljko| last3 = Janković| first3 = Slobodan| last4 = Stanojković| first4 = Tatjana| last5 = Ranković| first5 = Branislav| journal = Food and Chemical Toxicology| volume = 53| pages = 112–118| pmid = 23220145}}{{cite journal | doi = 10.1016/j.phymed.2012.07.012 | title = Chemical composition of three Parmelia lichens and antioxidant, antimicrobial and cytotoxic activities of some their major metabolites | date = 2012 | last1 = Manojlović | first1 = Nedeljko | last2 = Ranković | first2 = Branislav | last3 = Kosanić | first3 = Marijana | last4 = Vasiljević | first4 = Perica | last5 = Stanojković | first5 = Tatjana | journal = Phytomedicine | volume = 19 | issue = 13 | pages = 1166–1172 | pmid = 22921748 }}