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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:43445 ;
ChemSpider	570881 ;
PubChem CID	656496;
CompTox Dashboard (EPA)	DTXSID90349637 ;
	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 Key: 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/s1 Key: YONHOSLUBQJXPR-KCQAQPDRBL;
	SMILES C[C@H]1CCCC2=CC[C@@H](C[C@]12C)C(=C)C;
Properties
Chemical formula	C15H24
Molar mass	204.357 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).
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	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.
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.

External links

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[1] Terpene Biosynthesis Archived February 25, 2007, at the Wayback Machine, Chem 549, College of Pharmacy, University of Arizona

[pmid8440737-2] 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. PMID 8440737.

[pmid7080052-3] 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.