Aristolochene
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
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 ?)
Infobox references

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.[1]

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.[2] PR toxin has been implicated in incidents of mycotoxicoses resulting from eating contaminated grains.[3]

References

  1. ↑ Terpene Biosynthesis Archived February 25, 2007, at the Wayback Machine, Chem 549, College of Pharmacy, University of Arizona
  2. ↑ Proctor RH, Hohn TM (February 1993). "Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from Penicillium roqueforti". J. Biol. Chem. 268 (6): 4543–8. doi:10.1016/S0021-9258(18)53644-9. PMID 8440737.
  3. ↑ Chen FC, Chen CF, Wei RD (1982). "Acute toxicity of PR toxin, a mycotoxin from Penicillium roqueforti". Toxicon. 20 (2): 433–41. doi:10.1016/0041-0101(82)90006-X. PMID 7080052.
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