Atromentin

Atromentin

2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone Structural formula of atromentin
Names
IUPAC name 2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione
Other names 2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone
Identifiers
CAS Number	519-67-5 N
ChemSpider	89570 Y
Jmol 3D model	Interactive image
PubChem	99148
InChI InChI=1S/C18H12O6/c19-11-5-1-9(2-6-11)13-15(21)17(23)14(18(24)16(13)22)10-3-7-12(20)8-4-10/h1-8,19-21,24H Y Key: FKQQKMGWCJGUCS-UHFFFAOYSA-N Y InChI=1S/C18H12O6/c19-11-5-1-9(2-6-11)13-15(21)17(23)14(18(24)16(13)22)10-3-7-12(20)8-4-10/h1-8,19-21,24H Key: FKQQKMGWCJGUCS-UHFFFAOYSA-N
SMILES C1=CC(=CC=C1C2=C(C(=O)C(=C(C2=O)O)C3=CC=C(C=C3)O)O)O
Properties
Chemical formula	C18H12O6
Molar mass	324.29 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is YN ?)
Infobox references

Atromentin is a natural chemical compound found in Agaricomycetes fungi in the orders Agaricales and Thelephorales. It can also be prepared by laboratory synthesis. Chemically, it is a polyphenol and a benzoquinone.

Occurrences

Atromentin has been found in cultures of Clitocybe subilludens and in extracts of Hydnellum peckii. The first enzymes in its biosynthesis have been characterized in Tapinella panuoides. One of those is called atromentin synthetase.

Biological activities

A number of in vitro biological actives of atromentin have been studied. Atromentin possesses in vitro antibacterial activity, inhibiting the enzyme enoyl-acyl carrier protein reductase (essential for the biosynthesis of fatty acids) in the bacteria Streptococcus pneumoniae. Atromentin has been shown to be a smooth muscle stimulant. It also induces apoptosis in isolated human leukemia U937 cells. It is also an anticoagulant.