pentalenene
cyclopenta[c]pentalene, 1,2,3,3a,5a,6,7,8-octahydro-1,4,7,7-tetramethyl-, (1R,3aS,5aS)-
 
Notes:
None found
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CAS Number: 62065-26-3Picture of molecule3D/inchi
XlogP3-AA: 4.70 (est)
Molecular Weight: 204.35628000
Formula: C15 H24
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 0.07675 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for pentalenene usage levels up to:
 not for fragrance use.
 
Recommendation for pentalenene flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 194140
National Institute of Allergy and Infectious Diseases: Data
 (1R,3aS,5aS)-1,4,7,7-tetramethyl-2,3,3a,5a,6,8-hexahydro-1H-cyclopenta[h]pentalene
Chemidplus: 0062065263
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References:
 (1R,3aS,5aS)-1,4,7,7-tetramethyl-2,3,3a,5a,6,8-hexahydro-1H-cyclopenta[h]pentalene
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 194140
Pubchem (sid): 135172459
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C01841
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
 cyclopenta[c]pentalene, 1,2,3,3a,5a,6,7,8-octahydro-1,4,7,7-tetramethyl-, (1R,3aS,5aS)-
(1alpha,3aalpha,5abeta,8aR*)-1,2,3,3a,5a,6,7,8-octahydro-1,4,7,7-tetramethyl cyclopenta(c)pentalene
(1R,3aS,5aS)-1,4,7,7-tetramethyl-2,3,3a,5a,6,8-hexahydro-1H-cyclopenta[h]pentalene
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Articles:
PubMed: Rhodium-catalyzed [5 + 2 + 1] cycloaddition of ene-vinylcyclopropanes and CO: reaction design, development, application in natural product synthesis, and inspiration for developing new reactions for synthesis of eight-membered carbocycles.
PubMed: Trimethylenemethane diyl mediated tandem cycloaddition reactions: mechanism based design of synthetic strategies.
PubMed: Computational-guided discovery and characterization of a sesquiterpene synthase from Streptomyces clavuligerus.
PubMed: Stabilizing Two Classical Antiaromatic Frameworks: Demonstration of Photoacoustic Imaging and the Photothermal Effect in Metalla-aromatics.
PubMed: Delocalization of charge and electron density in the humulyl cation—implications for terpene biosynthesis.
PubMed: Total synthesis of (±)-hippolachnin A.
PubMed: Pentalenene formation mechanisms redux.
PubMed: Novel 2-aminooctahydrocyclopentalene-3a-carboxamides as potent CCR2 antagonists.
PubMed: Heterologous expression of pentalenene synthase (PSS) from Streptomyces UC5319 in Xanthophyllomyces dendrorhous.
PubMed: Effect of isotopically sensitive branching on product distribution for pentalenene synthase: support for a mechanism predicted by quantum chemistry.
PubMed: Near-infrared thermochromic diazapentalene dyes.
PubMed: 1,2-Dihydropentalenes from fulvenes by [6 + 2] cycloadditions with 1-isopropenylpyrrolidine.
PubMed: [Overview of 40 years' chemical study].
PubMed: Enantioselective synthesis of (-)-pentalenene.
PubMed: Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlI, a cytochrome P450 of Streptomyces avermitilis.
PubMed: Syntheses of biologically active natural products and leading compounds for new pharmaceuticals employing effective construction of a polycyclic skeleton.
PubMed: Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlH, a non-heme iron dioxygenase of Streptomyces avermitilis.
PubMed: A gene cluster for biosynthesis of the sesquiterpenoid antibiotic pentalenolactone in Streptomyces avermitilis.
PubMed: Theoretical studies on farnesyl cation cyclization: pathways to pentalenene.
PubMed: Tandem cyclisations involving alpha-ketenyl alkyl radicals. New syntheses of the natural triquinanes pentalenene and modhephene.
PubMed: Expression and mechanistic analysis of a germacradienol synthase from Streptomyces coelicolor implicated in geosmin biosynthesis.
PubMed: A highly abbreviated synthesis of pentalenene by means of the squarate ester cascade.
PubMed: Stereocontrolled synthesis of triazacyclopenta[cd]pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines.
PubMed: Structure, mechanism and function of prenyltransferases.
PubMed: Pentalenene synthase. Analysis of active site residues by site-directed mutagenesis.
PubMed: Eubacterial diterpene cyclase genes essential for production of the isoprenoid antibiotic terpentecin.
PubMed: Intramolecular C-H insertion reactions of (eta(5)-cyclopentadienyl)dicarbonyliron carbene complexes: scope of the reactions and application to the synthesis of (+/-)-sterpurene and (+/-)-pentalenene.
PubMed: Identification and sequencing of a cytochrome P450 gene cluster from Bradyrhizobium japonicum.
PubMed: Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology.
PubMed: Crystallization and preliminary X-ray diffraction analysis of recombinant pentalenene synthase.
PubMed: Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319.
PubMed: Terpenoid biosynthesis and the stereochemistry of enzyme-catalysed allylic addition-elimination reactions.
PubMed: Partial purification and characterization of pentalenene synthase.
PubMed: Regulation of enzymes involved in the biosynthesis of the sesquiterpene antibiotic pentalenolactone in Streptomyces arenae.
PubMed: Studies on biosynthesis of pentalenolactone. V isolation of deoxypentalenylglucuron.
PubMed: Studies on the biosynthesis of pentalenolactone. III. Isolation of a biosynthetic intermediate hydrocarbon, pentalenene.
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