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Aristolochene
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Aristolochene

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Aristolochene
Aristolochene.png
Names
IUPAC name
7α-Eremophila-9,11-diene
Systematic IUPAC name
(4S,4aR,6S)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene
Other names
(+)-Aristolochene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h9,12-13H,1,5-8,10H2,2-4H3/t12-,13-,15+/m0/s1 checkY
    Key: YONHOSLUBQJXPR-KCQAQPDRSA-N checkY
  • InChI=1/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h9,12-13H,1,5-8,10H2,2-4H3/t12-,13-,15+/m0/s1
    Key: YONHOSLUBQJXPR-KCQAQPDRBL
  • C[C@H]1CCCC2=CC[C@@H](C[C@]12C)C(=C)C
Properties
C15H24
Molar mass 204.357 g·mol−1
Density 0.894 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Aristolochene is a bicyclic sesquiterpene produced by certain fungi including the cheese mold Penicillium roqueforti. It is biosynthesized from farnesyl pyrophosphate by aristolochene synthase and is the parent hydrocarbon of a large variety of fungal toxins.

The substance was first isolated from Penicillium roqueforti, a fungus used to make blue cheeses like Roquefort, Danish Blue, Stilton cheese and gorgonzola.

Aristolochene is a precursor to PR toxin, a toxic chemical made in large amounts by Penicillium roqueforti. PR toxin has been implicated in incidents of mycotoxicoses resulting from eating contaminated grains.

Related Compounds


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