Aristolochene

Aristolochene
Names

IUPAC name (4S,4aR,6S)-6-Isopropenyl-4,4a-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene
Other names (+)-Aristolochene
Identifiers
CAS Number	123408-96-8^N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:43445^Y
ChemSpider	570881^Y
PubChem	656496
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/s1^Y Key: YONHOSLUBQJXPR-KCQAQPDRSA-N^Y 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
SMILES C[C@H]1CCCC2=CC[C@@H](C[C@]12C)C(=C)C
Properties
Chemical formula	C₁₅H₂₄
Molar mass	204.36 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 ^YN ?)
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 the toxin known as PR toxin, made in large amounts by Penicillium roqueforti.^[2] PR-toxin has been implicated in incidents of mycotoxicoses resulting from eating contaminated grains.^[3]

Related Compounds

References

↑ Terpene Biosynthesis Archived February 25, 2007, at the Wayback Machine., Chem 549, College of Pharmacy, University of Arizona
↑ 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. PMID 8440737. Retrieved 2008-12-03.
↑ 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. Retrieved 2008-12-03.

External links

(+)-Aristolochene at ChEBI

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