cyclooctane
octamethylene
Identification
| Name | cyclooctane |
| IUPAC | cyclooctane |
| CAS Number | 292-64-8 |
| EINECS | 206-031-8 |
| FDA UNII | KKZ3KBS654 |
| Molecular Formula | C8 H16 |
| Molecular Weight | 112.21552000 |
| MDL Number | MFCD00004162 |
| Nikkaji Number | J31.686E |
| Beilstein | 1900349 |
| XlogP3 | 4.50 (est) |
Regulatory
Physical Properties
| Appearance | colorless liquid or solid (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.83600 to 0.83800 @ 20.00 °C. |
| Pounds per Gallon - (est). | 6.964 to 6.981 |
| Refractive Index | 1.45800 to 1.45900 @ 20.00 °C. |
| Melting Point | 14.00 to 15.00 °C. @ 760.00 mm Hg |
| Boiling Point | 149.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 16.000000 mmHg @ 37.70 °C. |
| Flash Point | 82.00 °F. TCC ( 28.00 °C. ) |
| logP (o/w) | 4.450 |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| 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 cyclooctane usage levels up to | not for fragrance use. |
| Recommendation for cyclooctane flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
Synonyms
octamethylene
PubMed:
Carbon-Hydrogen Activation of Cycloalkanes by Cyclopentadienylcarbonylrhodium-A Lifetime Enigma.
PubMed:
A novel synthetic approach to the bicyclo[5.3.1]undecan-11-one framework of vinigrol.
PubMed:
Development of GoSlo-SR-5-69, a potent activator of large conductance Ca2+-activated K+ (BK) channels.
PubMed:
Construction of the basic skeleton of ophiobolin A and variecolin.
PubMed:
Diels-Alder reaction for tumor pretargeting: in vivo chemistry can boost tumor radiation dose compared with directly labeled antibody.
PubMed:
Kinetics study of the reaction of OH radicals with C5-C8 cycloalkanes at 240-340 K using the relative rate/discharge flow/mass spectrometry technique.
PubMed:
Highly active catalysts for the transfer dehydrogenation of alkanes: synthesis and application of novel 7-6-7 ring-based pincer iridium complexes.
PubMed:
Complexes with hybrid phosphorus-NHC ligands: pincer-type Ir hydrides, dinuclear Ag and Ir and tetranuclear Cu and Ag complexes.
PubMed:
Interpreting medium ring canonical conformers by a triangular plane tessellation of the macrocycle.
PubMed:
Oxorhenium(V) complexes of quinoline and isoquinoline carboxylic acids--synthesis, structural characterization and catalytic application in epoxidation reactions.
PubMed:
Doped graphene as a metal-free carbocatalyst for the selective aerobic oxidation of benzylic hydrocarbons, cyclooctane and styrene.
PubMed:
Enzyme-catalyzed synthesis of aliphatic-aromatic oligoamides.
PubMed:
The great diversity of HMX conformers: probing the potential energy surface using CCSD(T).
PubMed:
Proton-bridge motions in amine conjugate acid ions having intramolecular hydrogen bonds to hydroxyl and amine groups.
PubMed:
Oxidation of cycloalkanes by H2O2 using a copper-hemicryptophane complex as a catalyst.
PubMed:
Two- and three-dimensional standing waves in a reaction-diffusion system.
PubMed:
Exploring the energy landscapes of flexible molecular loops using higher-dimensional continuation.
PubMed:
Heterometallic Co(III)4Fe(III)2 Schiff base complex: structure, electron paramagnetic resonance, and alkane oxidation catalytic activity.
PubMed:
Improving the affinity and activity of CYP101D2 for hydrophobic substrates.
PubMed:
Catalytic hydrogen evolution from a covalently linked dicobaloxime.
PubMed:
Attenuated total reflection infrared difference spectroscopy (ATR-IRDS) for quantitative reaction monitoring.
PubMed:
Tetradentate Schiff base ligands and their complexes: synthesis, structural characterization, thermal, electrochemical and alkane oxidation.
PubMed:
Correlations between conjugation length, macromolecular dynamics, and photophysics of phenylene-vinylene/aliphatic multiblock copolymers.
PubMed:
Reactions of OH radicals with C6-C10 cycloalkanes in the presence of NO: isomerization of C7-C10 cycloalkoxy radicals.
PubMed:
Synthesis and antimicrobial evaluation of some new cyclooctanones and cyclooctane-based heterocycles.
PubMed:
Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry.
PubMed:
Membrane labeling and immobilization via copper-free click chemistry.
PubMed:
Synthetic studies on dicyclopenta[a,d]cyclooctane terpenoids: construction of the core structure of fusicoccins and ophiobolins on the route involving a Wagner-Meerwein rearrangement.
PubMed:
Efficient catalytic cycloalkane oxidation employing a "helmet" phthalocyaninato iron(III) complex.
PubMed:
Atmospheric-pressure, liquid-phase, selective aerobic oxidation of alkanes catalysed by metal-organic frameworks.
PubMed:
Development of Photocrosslinkable Urethane-Doped Polyester Elastomers for Soft Tissue Engineering.
PubMed:
Rh-catalyzed [7 + 1] cycloaddition of buta-1,3-dienylcyclopropanes and CO for the synthesis of cyclooctadienones.
PubMed:
Screening of a minimal enriched P450 BM3 mutant library for hydroxylation of cyclic and acyclic alkanes.
PubMed:
Synthesis of oligoribonucleic acid conjugates using a cyclooctyne phosphoramidite.
PubMed:
Labeling study of avidin by modular method for affinity labeling (MoAL).
PubMed:
Topology of cyclo-octane energy landscape.
PubMed:
Citric-acid-derived photo-cross-linked biodegradable elastomers.
PubMed:
Structure-activity analysis of vinylogous urea inhibitors of human immunodeficiency virus-encoded ribonuclease H.
PubMed:
Metalloradical-catalyzed aliphatic carbon-carbon activation of cyclooctane.
PubMed:
Synthesis and characterization of a biodegradable elastomer featuring a dual crosslinking mechanism.
PubMed:
Solvation shell structure of cyclooctylpyranone in water solvent and its comparative structure, dynamics and dipole moment in HIV protease.
PubMed:
Clickable fluorophores for biological labeling--with or without copper.
PubMed:
Effects of native organic material and water on sorption properties of reference diesel soot.
PubMed:
Zirconium complex of an [OSSO]-type diphenolate ligand bearing trans-1,2-cyclooctanediylbis(thio) core: synthesis, structure, and isospecific 1-hexene polymerization.
PubMed:
Ring strain energy in the cyclooctyl system. The effect of strain energy on [3 + 2] cycloaddition reactions with azides.
PubMed:
Characterization of sorbent properties of soil organic matter and carbonaceous geosorbents using n-alkanes and cycloalkanes as molecular probes.
PubMed:
Transformation of the hexagonal-structure clathrate hydrate of cyclooctane to a low-symmetry form below 167 k.
PubMed:
Dual types of spherulites in poly(octamethylene terephthalate) confined in thin-film growth.
PubMed:
Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity.
PubMed:
Contiguously substituted cyclooctane polyols. configurational assignments via (1)H NMR correlations and symmetry considerations.
PubMed:
Algorithmic dimensionality reduction for molecular structure analysis.
PubMed:
Design, synthesis and pharmacological evaluation of hybrid molecules out of quinazolinimines and lipoic acid lead to highly potent and selective butyrylcholinesterase inhibitors with antioxidant properties.
PubMed:
Nonelectrical poling in ferroelectric polythioureas.
PubMed:
2-Chloro-12-phenyl-6,7,8,9,10,11-hexa-hydro-cyclo-octa-[b]quinoline.
PubMed:
Catalytic ring expansion, contraction, and metathesis-polymerization of cycloalkanes.
PubMed:
Packing in three cyclooctitol acetates.
PubMed:
Studies towards the total synthesis of di- and sesterterpenes with dicyclopenta[a,d]cyclooctane skeletons. Three-component approach to the A/B rings building block.
PubMed:
1'-Methylcyclooctane-1-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-2,2''-dione and 1,1'-dimethylpiperidine-3-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-2'',4-dione.
PubMed:
A hydrophilic cyclodextrin duplex forming supramolecular assemblies by physical cross-linking of a biopolymer.
PubMed:
Cyclooctane tropospheric degradation initiated by reaction with C1 atoms.
PubMed:
Synthesis and catalytic properties in olefin epoxidation of novel iron(II) complexes with pyridine-containing macrocycles bearing an aminopropyl pendant arm.
PubMed:
Emission switching of ferrocenyl Schiff bases and a representative ruthenium complex in alkaline DMSO: absorption, electrochemical and microstructural studies.
PubMed:
Structure-activity relationships of methoctramine-related polyamines as muscarinic antagonist: effect of replacing the inner polymethylene chain with cyclic moieties.
PubMed:
Analysis of guazatine mixture by LC and LC-MS and antimycotic activity determination of principal components.
PubMed:
Cucurbituril binding of trans-[{PtCl(NH3)2}2(micro-NH2(CH2)8NH2)]2+ and the effect on the reaction with cysteine.
PubMed:
Encapsulation of a guest molecule in a strained form: an extended 36-membered dodecanuclear manganese metallamacrocycle that accommodates a cyclooctane in the S4 symmetry conformation.
PubMed:
Transition-metal (Ti,V,Cr,Mn,Fe,Co,Cu) containing ordered nanoporous materials: novel heterogeneous catalysts for selective oxidation reactions.
PubMed:
Homobivalent quinazolinimines as novel nanomolar inhibitors of cholinesterases with dirigible selectivity toward butyrylcholinesterase.
PubMed:
Saturated hydrocarbon-benzene complexes: theoretical study of cooperative CH/pi interactions.
PubMed:
From common carbohydrates to enantiopure cyclooctane polyols and glycomimetics via deoxygenative zirconocene ring contraction.
PubMed:
Triplet energy back transfer in conjugated polymers with pendant phosphorescent iridium complexes.
PubMed:
Supramolecular assemblies of a new series of gemini-type schiff base amphiphiles at the air/water interface: in situ coordination, interfacial nanoarchitectures, and spacer effect.
PubMed:
Self-inclusion behavior and circular dichroism of aliphatic chain-linked beta-cyclodextrin-viologen compounds and their reduced forms depending on the side of modification.
PubMed:
Three-carbon Dowd-Beckwith ring expansion reaction versus intramolecular 1,5-hydrogen transfer reaction: a theoretical study.
PubMed:
Studies toward the total synthesis of vinigrol. synthesis of the octalin ring.
PubMed:
Bayesian methods for the conformational classification of eight-membered rings.
PubMed:
Europium(II) and ytterbium(II) cyclic organohydroborates with agostic interactions.
PubMed:
Enantioselective route from carbohydrates to cyclooctane polyols.
PubMed:
Exploratory studies aimed at a synthesis of vinigrol. 2. Attempts to exploit ring-closing metathesis for construction of the central cyclooctane belt.
PubMed:
Conformational investigations on analogs of inflammation response inducing chemotactic tripeptide fMLP.
PubMed:
Boronic acid based modular fluorescent sensors for glucose.
PubMed:
Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 3. Effect of replacing the inner polymethylene chain with cyclic moieties.
PubMed:
Phase relationships and thermodynamic interactions of isotactic poly(1-butene) and organic solvent systems.
PubMed:
A combined experimental and computational study of dihydrido(phosphinooxazoline)iridium complexes.
PubMed:
Effect of surface wettability on the adhesion of proteins.
PubMed:
Mechanistic studies of the transfer dehydrogenation of cyclooctane catalyzed by iridium bis(phosphinite) p-XPCP pincer complexes.
PubMed:
Alkane oxidation via photochemical excitation of a self-assembled molecular cage.
PubMed:
Peptide helices with pendant cycloalkane rings. Characterization of conformations of 1-aminocyclooctane-1-carboxylic acid (Ac8c) residues in peptides.
PubMed:
Aromatic vs aliphatic C-H cleavage of alkyl-substituted pyridines by (PNPiPr)Re compounds.
PubMed:
Direct investigation of the fate of NAPL contaminations in a hydrating cement matrix by means of magnetic resonance techniques.
PubMed:
Iridium bis(phosphinite) p-XPCP pincer complexes: highly active catalysts for the transfer dehydrogenation of alkanes.
PubMed:
Europium(II) and ytterbium(II) cyclic organohydroborates: an europium(II) complex with an agostic interaction.
PubMed:
The C7-C10 cycloalkanes revisited.
PubMed:
Diazacoronand linked beta-cyclodextrin dimer complexes of Brilliant Yellow tetraanion and their sodium(I) analogues.
PubMed:
Mechanism of alkane transfer-dehydrogenation catalyzed by a pincer-ligated iridium complex.
PubMed:
Bivalent biogenic amine reuptake inhibitors.
PubMed:
Evaluation of different formulation studies on air-filled polymeric microcapsules by multivariate analysis.
PubMed:
Indigo production by Escherichia coli carrying the phenol hydroxylase gene from Acinetobacter sp strain ST-550 in a water-organic solvent two-phase system.
PubMed:
Synthesis and pharmacological activity of fluorescent histamine H1 receptor antagonists related to mepyramine.
PubMed:
From hydrocarbons to polyols. Cyclooctatetraene to novel cyclooctitols.
PubMed:
Structural characterisation of bisintercalation in higher-order DNA at a junction-like quadruplex.
PubMed:
Multiple active intermediates in oxidation reaction catalyzed by synthetic heme-thiolate complex relevant to cytochrome p450.
PubMed:
Selective oxidation of cyclooctane to cyclootanone with molecular oxygen in the presence of compressed carbon dioxide.
PubMed:
The effect of a hydroxy protecting group on the PtCl2-catalyzed cyclization of dienynes--a novel, efficient, and selective synthesis of carbocycles.
PubMed:
Synthesis of enantiomerically pure, highly functionalized, medium-sized carbocycles from carbohydrates: formal total synthesis of (+)-calystegine b(2).
PubMed:
A silica monolithic column prepared by the sol-gel process for enantiomeric separation by capillary electrochromatography.
PubMed:
Total synthesis of (+/-)-asteriscanolide.
PubMed:
Conformational Study of Oxacyclooctan-2-one by Dynamic NMR Spectroscopy and Computational Methods.
PubMed:
Flexibility vs Rigidity of Singly and Doubly Tethered Biphenyls: Structure, Dynamic Stereochemistry, and Resolution of Tribenzo[a,c,f]cyclooctane, Tetrabenzo[a,de,h,kl]bicyclo[6.6.0]tetradecane, and Their Alkyl Derivatives.
PubMed:
Trapping-mediated dissociative chemisorption of cycloalkanes on Ru(001) and Ir(111): influence of ring strain and molecular geometry on the activation of C-C and C-H bonds.
PubMed:
Separation of enantiomers by open capillary electrochromatography on polysiloxane-bonded permethyl-beta-cyclodextrin.
PubMed:
Air-filled polymeric microcapsules from emulsions containing different organic phases.
PubMed:
Synthesis and structures of heterocyclic azidogallanes [(CH3)ClGaN3]4 and [(CH3)BrGaN3]3 en route to [(CH3)HGaN3]x: an inorganic precursor to GaN.
PubMed:
10-Deacetyl baccatin III dimethyl sulfoxide disolvate.
PubMed:
A new thioether-ligated iron porphyrin as a model of a protonated form of P450 active site.
PubMed:
A [4 + 4] 2-pyridone approach to taxol. 3. Stereocontrol during elaboration of the cyclooctane.
PubMed:
Enantiomer separation by capillary electrochromatography on a cyclodextrin-modified monolith.
PubMed:
Catalytic oxidation with a non-heme iron complex that generates a low-spin Fe(III)OOH intermediate
PubMed:
Test liquids for quantitative MRI measurements of self-diffusion coefficient in vivo.
PubMed:
Syntheses and evaluation of amidinobenzofuran derivatives as tryptase inhibitors.
PubMed:
Renal targeting of arginine-vasopressin by modification with carbohydrates at the tyrosine side chain.
PubMed:
Enantiomer separation by pressure-supported electrochromatography using capillaries packed with Chirasil-Dex polymer-coated silica.
PubMed:
Specific renal delivery of sugar-modified low-molecular-weight peptides.
PubMed:
Appearance of a stress-response protein, phage-shock protein A, in Escherichia coli exposed to hydrophobic organic solvents.
PubMed:
Hydrophilicity of polymers and soft tissue responses: a quantitative analysis.
PubMed:
Anti-AIDS agents--XXVI. Structure-activity correlations of gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues.
PubMed:
Anesthetic and convulsant properties of aromatic compounds and cycloalkanes: implications for mechanisms of narcosis.
PubMed:
Regional distribution of rat electroolfactogram.
PubMed:
Enantiomer separation using mobile and immobile cyclodextrin derivatives with electromigration.
PubMed:
In vivo evaluation of polyurethanes based on novel macrodiols and MDI.
PubMed:
Structure-activity relationship studies with symmetric naphthalenesulfonic acid derivatives. Synthesis and influence of spacer and naphthalenesulfonic acid moiety on anti-HIV-1 activity.
PubMed:
[Synthesis of N-substituted polymethylene dicarboxamides as inducers of differentiation].
PubMed:
Potential anti-AIDS naphthalenesulfonic acid derivatives. Synthesis and inhibition of HIV-1 induced cytopathogenesis and HIV-1 and HIV-2 reverse transcriptase activities.
PubMed:
Lecithin organogel as matrix for transdermal transport of drugs.
PubMed:
Structure of (+/-)-(1R*,6S*)-1-benzyloxy-8,11,11-trimethyl-6-phenylthiobicyclo [5.3.1 ]undec-7-en-3-one.
PubMed:
The structure of (4R*,7R*)-4,10,11,11-tetramethyl-5- oxobicyclo[5.3.1]undec-1(10)-en-4-carbaldehyde.
PubMed:
Structure of (+/-)-(1R*,4S*,6S*)-1-benzyloxy-4,8,11,11-tetramethyl-6- phenylthio-bicyclo[5.3.1]undec-7-en-3-one.
PubMed:
Photocleavage of DNA and photofootprinting of E. coli RNA polymerase bound to promoter DNA by azido-9-acridinylamines.
PubMed:
Solubility in binary solvent systems: 8. Estimation of binary alkane plus p-dioxane solvent nonideality from measured anthracene solubilities.
PubMed:
Developmental toxicity of N,N1-bis(dichloroacetyl)-1,8-octamethylene diamine: effects of in utero exposure on the postnatal murine immune system.
PubMed:
Cross-linking between histones and DNA following treatment with a series of dimethane sulphonate esters.
PubMed:
Outer membrane porin proteins F, P, and D1 of Pseudomonas aeruginosa and PhoE of Escherichia coli: chemical cross-linking to reveal native oligomers.
PubMed:
Loss of hepatic monooxygenase activities, glutathione, and 'green pigment' formation after the administration of vinyl-cyclooctane to mice.
PubMed:
[Physiological activity of polymethylene and polyoxyethylene bis-(2-amino-1,3-diazepiniuim) iodides].
PubMed:
Formation of a polymethylene bis(disulfide) intersubunit cross-link between cysteine-281 residues in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase using octamethylene bis(methane[35S]thiosulfonate).
PubMed:
Solubility in binary solvent systems I: Specific versus nonspecific interactions.
PubMed:
[Thin-layer chromatographic determination of N,N'-bis-dichloroacetyl-1,8-octamethylene diamine for the elucidation of deceptive strategems in the expertise of paternity].
PubMed:
[Hypocholesterolemic effect and lipid protection of the arterial wall by dimethyl-1,1-dioxa-2,8-hydroxyethyl-5-sila-1-aza-5-cyclooctane (T.E.A.S)].
PubMed:
[Synthesis of cyclooctane-1,5-dione derivatives (author's transl)].
PubMed:
The fixation of complement and the activated first component (C1) of complement by complexes formed between antibody and divalent hapten.
PubMed:
Inhibition of fly head acetylcholinesterase by bis-[(m-hydroxyphenyl)-trimethylammonium iodide] esters of polymethylenedicarbamic acids.
PubMed:
The metabolism of the octamethylene-1,8-dithiol moiety of bis(O-acetylthiamine)octamethylene-18,-disulfide in rat and man.
PubMed:
[Histochemical studies on the psychomotor end plate of the skeletal muscles on the white mouse after administration of the cholinesterase inhibitors BC 16 (hexamethylene-bis-carbaminoylcholine) and BC 47 (octamethylene-bis-carbaminoyl-m-trimethylammoniumphenol)].
PubMed:
[Interaction of d-tubocurarine, eserine and depolarizing substances in isolated rat diaphram, studied with octamethylene-biscarbaminoylcholine].
PubMed:
The heats of combustion of cyclopentane, cyclohexane, cycloheptane and cyclooctane.