Aristolochene

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	123408-96-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:43445 ;
ChemSpider	570881 ;
PubChem CID	656496;
UNII	459BG6ZY5H ;
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). verify (what is ?) 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]

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. doi:10.1016/S0021-9258(18)53644-9. 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.

[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. doi:10.1016/S0021-9258(18)53644-9. 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.

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