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{{chembox |
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{{chembox |
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| verifiedrevid = 456241327 |
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|ImageFile=Aristolochene.png |
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| verifiedrevid = 457152393 |
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|ImageSize=200px |
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| ImageFile=Aristolochene.png |
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|IUPACName=(4''S'',4a''R'',6''S'')-6-Isopropenyl-4,4a-dimethyl-2,3,4,5,6,7-hexahydro-1''H''-naphthalene |
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| ImageSize=200px |
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|OtherNames=(+)-Aristolochene |
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| IUPACName=7α-Eremophila-9,11-diene |
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| SystematicName=(4''S'',4a''R'',6''S'')-4,4a-Dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene |
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| OtherNames=(+)-Aristolochene |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 123408-96-8 --> |
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| CASNo=123408-96-8 |
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| ChEBI = 43445 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 459BG6ZY5H |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 43445 |
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| PubChem=656496 |
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| PubChem=656496 |
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| SMILES=C1CCCC2=CC(C12C)C(=C)C |
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| SMILES=C1CCCC2=CC(C12C)C(=C)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 570881 |
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| ChemSpiderID = 570881 |
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| 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 |
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| 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 |
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| InChIKey = YONHOSLUBQJXPR-KCQAQPDRBL |
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| InChIKey = YONHOSLUBQJXPR-KCQAQPDRBL |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YONHOSLUBQJXPR-KCQAQPDRSA-N |
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| StdInChIKey = YONHOSLUBQJXPR-KCQAQPDRSA-N |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>15</sub>H<sub>24</sub> |
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| C=15 | H=24 |
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| Appearance= |
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| MolarMass=204.35 g/mol |
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| Density=0.894 g/mL |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt= |
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'''Aristolochene''' is a ] ] produced by certain ] including the ] ] '']''. It is ] from ] by ] and is the parent hydrocarbon of a large variety of ].<ref>, Chem 549, College of Pharmacy, University of Arizona</ref> |
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'''Aristolochene''' is a ] ] produced by certain ] including the ] ] '']''. It is ] from ] by ] and is the parent hydrocarbon of a large variety of ].<ref> {{webarchive |url=https://web.archive.org/web/20070225231653/http://www.pharmacy.arizona.edu/faculty/moorelab/classes/chem549/terpenes.pdf |date=February 25, 2007 }}, Chem 549, College of Pharmacy, University of Arizona</ref> |
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The substance was first isolated from ''Penicillium roqueforti'', a fungus used to make blue cheeses like ], ], ] and ]. |
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Aristolochene is a precursor to ], a toxic chemical made in large amounts by ''Penicillium roqueforti''.<ref name="pmid8440737">{{cite journal|vauthors=Proctor RH, Hohn TM |title=Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from ''Penicillium roqueforti'' |journal=J. Biol. Chem. |volume=268 |issue=6 |pages=4543–8 |date=February 1993 |doi=10.1016/S0021-9258(18)53644-9 |pmid=8440737 |url=http://www.jbc.org/cgi/pmidlookup?view=long&pmid=8440737|doi-access=free }}</ref> PR toxin has been implicated in incidents of ] resulting from eating contaminated grains.<ref name="pmid7080052">{{cite journal |vauthors=Chen FC, Chen CF, Wei RD |title=Acute toxicity of PR toxin, a mycotoxin from ''Penicillium roqueforti'' |journal=Toxicon |volume=20 |issue=2 |pages=433–41 |year=1982 |pmid=7080052 |doi= 10.1016/0041-0101(82)90006-X|bibcode=1982Txcn...20..433C }}</ref> |
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== Related Compounds == |
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==References== |
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==References== |
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==External links== |
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