{{Chembox <!-- Images --> | ImageFile = Necatorin.svg | ImageSize = 200px | ImageAlt = <!-- Names --> | IUPACName = 11-Hydroxychromeno[5,6-''c'']cinnolin-2-one | OtherNames = Necatorine <!-- Sections --> | Section1 = {{Chembox Identifiers | CASNo = 89915-35-5 | ChemSpiderID = 19985336 | PubChem = 135554414 | SMILES = C1=CC=C2C(=C1)C3=C(C4=C(C=C3O)OC(=O)C=C4)N=N2 | InChI = 1S/C15H8N2O3/c18-11-7-12-9(5-6-13(19)20-12)15-14(11)8-3-1-2-4-10(8)16-17-15/h1-7,18H | InChIKey = WNQBVKOXDIYRFH-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | C = 15 | H = 8 | N = 2 | O = 3 | Appearance = | Density = | MeltingPtC = 220-225 | MeltingPt_ref = <ref>{{cite web | url = https://hmdb.ca/metabolites/HMDB0039035 | title = Necatorine | work = Human Metabolome Database }}</ref> | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = Mutagenic | FlashPt = | AutoignitionPt = }} }}
'''Necatorin''' is a highly mutagenic chemical compound with the molecular formula {{chem2|C15H8N2O3}}. It is found in some mushrooms including ''Lactarius turpis'' (ugly milk-cap; older: L. necator), from which it was first isolated and characterized.<ref>{{cite journal | doi = 10.1016/S0031-9422(00)97723-9 | title = Necatorin, a highly mutagenic compound from Lactarius necator | date = 1983 | last1 = Suortti | first1 = Tapani | last2 = von Wright | first2 = Atte | last3 = Koskinen | first3 = Ari | journal = Phytochemistry | volume = 22 | issue = 12 | pages = 2873–2874 | bibcode = 1983PChem..22.2873S }}</ref> It tests positive in the Ames test, an assay for mutagenicity.<ref>{{cite journal | doi = 10.1016/0165-7992(83)90107-0 | title = Preliminary characterization of the mutagenic properties of 'necatorin', a strongly mutagenic compound of the mushroom Lactarius necator | date = 1983 | last1 = von Wright | first1 = Atte | last2 = Suortti | first2 = Tapani | journal = Mutation Research Letters | volume = 121 | issue = 2 | pages = 103–106 | pmid = 6348529 }}</ref> Crude extracts of ''L. necator'' are also highly mutagenic in a bacterial test system, and this effect it attributed to necatorin.<ref>{{cite journal | doi = 10.1016/0278-6915(91)90033-4| title = The mutagenicity of edible mushrooms in a histidine-independent bacterial test system| date = 1991| last1 = Grüter| first1 = A.| last2 = Friederich| first2 = U.| last3 = Würgler| first3 = F.E.| journal = Food and Chemical Toxicology| volume = 29| issue = 3| pages = 159–165| pmid = 2032657}}</ref>
Necatorin is present in ''L. necator'' at concentrations of 3 to 20 mg/kg, and blanching the mushroom can reduce it to about 25% of its original amount.<ref name=Suortti>{{cite journal | doi = 10.1016/0278-6915(84)90229-1 | title = Stability of necatorin, a highly mutagenic compound from Lactarius necator mushroom | date = 1984 | last1 = Suortti | first1 = T. | journal = Food and Chemical Toxicology | volume = 22 | issue = 7 | pages = 579–581 | pmid = 6547686 }}</ref> In boiling water, the chemical compound is stable except under acidic conditions (pH = 5).<ref name=Suortti/>
==References== {{reflist}}
Category:Mutagens Category:Lactones Category:Alkaloids Category:Heterocyclic compounds with 4 rings Category:Cinnolines Category:Chromanes Category:Phenols