Chemistry:Aristolochene
From HandWiki
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| Names | |
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| IUPAC name
7α-Eremophila-9,11-diene
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
PubChem CID
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| UNII | |
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| 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). | |
 verify (what is   ?)
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| Infobox references | |
Tracking categories (test):
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 , Chem 549, College of Pharmacy, University of Arizona
- ↑ "Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from Penicillium roqueforti". J. Biol. Chem. 268 (6): 4543–8. February 1993. doi:10.1016/S0021-9258(18)53644-9. PMID 8440737. http://www.jbc.org/cgi/pmidlookup?view=long&pmid=8440737.
- ↑ "Acute toxicity of PR toxin, a mycotoxin from Penicillium roqueforti". Toxicon 20 (2): 433–41. 1982. doi:10.1016/0041-0101(82)90006-X. PMID 7080052.
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