pentalenene
cyclopenta[c]pentalene, 1,2,3,3a,5a,6,7,8-octahydro-1,4,7,7-tetramethyl-, (1R,3aS,5aS)-
Identification
| Name | pentalenene |
| IUPAC | (1R,3aS,5aS)-1,4,7,7-tetramethyl-2,3,3a,5a,6,8-hexahydro-1H-cyclopenta[h]pentalene |
| CAS Number | 62065-26-3 |
| FDA UNII | Search |
| Molecular Formula | C15 H24 |
| Molecular Weight | 204.35628000 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 0.07675 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
No supplier data available
Potential Uses
Natural Occurrence
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
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 cationâimplications for terpene biosynthesis.
PubMed:
Total synthesis of (±)-hippolachninâ
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.