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Aristolochene

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: YONHOSLUBQJXPR-KCQAQPDRSA-N
  • 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/s1Key: YONHOSLUBQJXPR-KCQAQPDRBL
SMILES
  • C1CCCC2=CC(C12C)C(=C)C
Properties
Chemical formula C15H24
Molar mass 204.357 g·mol
Density 0.894 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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. Bibcode:1982Txcn...20..433C. doi:10.1016/0041-0101(82)90006-X. PMID 7080052.
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