{{Chembox <!-- Images --> | ImageFile = Chloroatranorin.svg | ImageSize = 200px | ImageAlt = <!-- Names --> | IUPACName = (3-Hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 5-chloro-3-formyl-2,4-dihydroxy-6-methylbenzoate | OtherNames = 5-Chloroatranorin <!-- Sections --> | 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 | MeltingPt_ref = <ref name=Elix>{{cite journal | doi = 10.1071/ch9751113 | title = Synthesis of para-β-orcinol depsides | date = 1975 | last1 = Elix | first1 = JA | last2 = Norfolk | first2 = S. | journal = Australian Journal of Chemistry | volume = 28 | issue = 5 | page = 1113 }}</ref> | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''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.<ref name=Pfau>{{cite journal| title = Constituents of lichens. IV. Chloroatranorin | author = Pfau, Alexander S. | journal = Helvetica Chimica Acta | date = 1934 | volume = 17 | pages = 1319–1328 }}</ref> It is the most common chlorine-containing depside in lichens, and has been identified in dozens of lichen species.<ref name="Dembitsky & Tolstikov 2003">{{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}}</ref>

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.<ref>{{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 }}</ref>

==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 (λ<sub>max</sub>) in the ultraviolet spectrum (in methanol solution) are 213, 252, and 282&nbsp;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&nbsp;cm<sup>−1</sup>. Chloroatranorin's molecular formula is C<sub>19</sub>H<sub>17</sub>ClO<sub>8</sub>; it has a molecular mass of 408.78&nbsp;grams per mole. In its purified crystalline form, its melting point is {{convert|208|–|208.5|C|F}}.<ref name="Huneck 1996">{{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}}</ref>

Chloroatranorin has been studied for its potential antioxidant, antimicrobial, and anticancer properties.<ref>{{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}}</ref><ref>{{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 }}</ref>

==References== {{reflist}}

Category:Benzoate esters Category:Methyl esters Category:Chloroarenes Category:Benzaldehydes Category:Polyphenols Category:Lichen products Category:Chlorine-containing natural products Category:Depsides