Necatorin

Last updated
Necatorin
Necatorin.svg
Names
IUPAC name
11-Hydroxychromeno[5,6-c]cinnolin-2-one
Other names
Necatorine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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
    Key: WNQBVKOXDIYRFH-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C3=C(C4=C(C=C3O)OC(=O)C=C4)N=N2
Properties
C15H8N2O3
Molar mass 264.240 g·mol−1
Melting point 220–225 °C (428–437 °F; 493–498 K) [1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Mutagenic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Necatorin is a highly mutagenic chemical compound with the molecular formula C15H8N2O3. It is found in some mushrooms including Lactarius turpis (ugly milk-cap; older: L. necator), from which it was first isolated and characterized. [2] It tests positive in the Ames test, an assay for mutagenicity. [3] Crude extracts of L. necator are also highly mutagenic in a bacterial test system, and this effect it attributed to necatorin. [4]

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. [5] In boiling water, the chemical compound is stable except under acidic conditions (pH = 5). [5]

References

  1. ↑ "Necatorine". Human Metabolome Database.
  2. ↑ Suortti, Tapani; von Wright, Atte; Koskinen, Ari (1983). "Necatorin, a highly mutagenic compound from Lactarius necator". Phytochemistry. 22 (12): 2873–2874. Bibcode:1983PChem..22.2873S. doi:10.1016/S0031-9422(00)97723-9.
  3. ↑ von Wright, Atte; Suortti, Tapani (1983). "Preliminary characterization of the mutagenic properties of 'necatorin', a strongly mutagenic compound of the mushroom Lactarius necator". Mutation Research Letters. 121 (2): 103–106. doi:10.1016/0165-7992(83)90107-0. PMID   6348529.
  4. ↑ Grüter, A.; Friederich, U.; Würgler, F.E. (1991). "The mutagenicity of edible mushrooms in a histidine-independent bacterial test system". Food and Chemical Toxicology. 29 (3): 159–165. doi:10.1016/0278-6915(91)90033-4. PMID   2032657.
  5. 1 2 Suortti, T. (1984). "Stability of necatorin, a highly mutagenic compound from Lactarius necator mushroom". Food and Chemical Toxicology. 22 (7): 579–581. doi:10.1016/0278-6915(84)90229-1. PMID   6547686.
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