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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | colorless clear liquid (est) |
| Assay: | 97.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Specific Gravity: | 0.92000 to 0.92400 @ 20.00 °C.
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| Pounds per Gallon - (est).: | 7.664 to 7.698
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| Refractive Index: | 1.53500 to 1.53900 @ 20.00 °C.
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| Boiling Point: | 140.00 to 141.00 °C. @ 760.00 mm Hg
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| Vapor Pressure: | 7.800000 mmHg @ 25.00 °C. |
| Flash Point: | 72.00 °F. TCC ( 22.00 °C. )
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| logP (o/w): | 3.080 |
| Soluble in: |
| | water, 77.29 mg/L @ 25 °C (est) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| 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 |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for 1,3,5,7-cyclooctatetraene usage levels up to: | | | not for fragrance use.
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| |
| Recommendation for 1,3,5,7-cyclooctatetraene flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (8) | annulene | | | cycloocta-1,3,5,7-tetraene | | | cyclooctatetraene |
Articles:
| PubMed:Investigation of the electronic structures of organolanthanide sandwich complex anions by photoelectron spectroscopy: 4f orbital contribution in the metal-ligand interaction. |
| PubMed:Formation and Electronic Structures of Organoeuropium Sandwich Nanowires. |
| PubMed:Hybridization of a flexible cyclooctatetraene core and rigid aceneimide wings for multiluminescent flapping π systems. |
| PubMed:Mechanism of intramolecular photostabilization in self-healing cyanine fluorophores. |
| PubMed:Bis-cyclooctatetraene tripalladium sandwich complexes. |
| PubMed:Diazadioxa[8]circulenes: planar antiaromatic cyclooctatetraenes. |
| PubMed:The contribution of reactive oxygen species to the photobleaching of organic fluorophores. |
| PubMed:Magnetic blocking at 10 K and a dipolar-mediated avalanche in salts of the bis(η8-cyclooctatetraenide) complex [Er(COT)2]-. |
| PubMed:Solvent versus temperature control over the infrared band shape and position in Fe(CO)3(η(4)-ligand) complexes. |
| PubMed:A first principles study of novel one-dimensional organic half-metal vanadium-cyclooctatetraene wire. |
| PubMed:Dithieno[3,4-b:3',4'-d]thiophene-annelated antiaromatic planar cyclooctatetraene with olefinic protons. |
| PubMed:Synthesis, structural analysis, and properties of [8]circulenes. |
| PubMed:Trinuclear palladium addition to unsaturated carbocycles. |
| PubMed:Small-molecule photostabilizing agents are modifiers of lipid bilayer properties. |
| PubMed:Narrowly dispersed silica supported osmium nanoparticles prepared by an organometallic approach: H2 and CO adsorption stoichiometry and hydrogenolysis catalytic activity. |
| PubMed:Hybridisation at the organic-metal interface: a surface-scientific analogue of Hückel's rule? |
| PubMed:High-resolution electron spectroscopy of lanthanide (Ce, Pr, and Nd) complexes of cyclooctatetraene: the role of 4f electrons. |
| PubMed:Antiaromatic planar cyclooctatetraene: a strategy for developing ambipolar semiconductors for field effect transistors. |
| PubMed:Multireference calculations for ring inversion and double bond shifting in cyclooctatetraene. |
| PubMed:Solvent-induced crystalline-state emission and multichromism of a bent π-surface system composed of dibenzocyclooctatetraene units. |
| PubMed:Air-stable bifunctional allylation reagents for the asymmetric synthesis of differentiated syn- and anti-1,3-diols. |
| PubMed:Azatrioxa[8]circulenes: planar anti-aromatic cyclooctatetraenes. |
| PubMed:A six-carbon 10π-electron aromatic system supported by group 3 metals. |
| PubMed:Generation of molecular complexity from cyclooctatetraene: preparation of optically active protected aminocycloheptitols and bicyclo[4.4.1]undecatriene. |
| PubMed:Binding of cerium monoxide to annulenes and buckybowls. |
| PubMed:On the Mechanisms of Cyanine Fluorophore Photostabilization. |
| PubMed:One-pot in situ fabrication of stable nanocaterpillars directly from polyacetylene diblock copolymers synthesized by mild ring-opening metathesis polymerization. |
| PubMed:A pass too far: dissociation of internal energy selected paracyclophane cations, theory and experiment. |
| PubMed:An experimental estimate of the relative aromaticity of the cyclooctatetraene dianion by fusion to dimethyldihydropyrene. |
| PubMed:Generation of molecular complexity from cyclooctatetraene using dienyliron and olefin metathesis methodology. |
| PubMed:Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction. |
| PubMed:Reversible and irreversible higher-order cycloaddition reactions of polyolefins with a multiple-bonded heavier group 13 alkene analogue: contrasting the behavior of systems with π-π, π-π*, and π-n+ frontier molecular orbital symmetry. |
| PubMed:Series of lanthanide organometallic single-ion magnets. |
| PubMed:Rhodium dinaphthocyclooctatetraene complexes: synthesis, characterization and catalytic activity in [5+2] cycloadditions. |
| PubMed:Calculations of the effects of methyl groups on the energy differences between cyclooctatetraene and bicyclo[4.2.0]octa-2,4,7-triene and between their iron tricarbonyl complexes. |
| PubMed:Electronic states and metal-ligand bonding of gadolinium complexes of benzene and cyclooctatetraene. |
| PubMed:Visual indication of mechanical damage using core-shell microcapsules. |
| PubMed:Cyanine fluorophore derivatives with enhanced photostability. |
| PubMed:Electron delocalization and aromaticity in low-lying excited states of archetypal organic compounds. |
| PubMed:Ru cyclooctatetraene precursors for MOCVD. |
| PubMed:Effect on ring current of the Kekulé vibration in aromatic and antiaromatic rings. |
| PubMed:Can an eight π-electron bare ring be planar? |
| PubMed:Analogues of the Lavallo-Grubbs compound Fe3(C8H8)3: equilateral, isosceles, and scalene metal triangles in trinuclear cyclooctatetraene complexes M3(C8H8)3 of the first row transition metals (M = Ti, V, Cr, Mn, Fe, Co, and Ni). |
| PubMed:Thermal reaction of [3,4]-benzo-8-substituted-3Z,5Z,7E-octatetraenes and quantum-chemical study of the (8π,6π)-electrocyclisation. |
| PubMed:Bonding nature and electron delocalization of An(COT)2, An = Th, Pa, U. |
| PubMed:The synergy between qualitative theory, quantitative calculations, and direct experiments in understanding, calculating, and measuring the energy differences between the lowest singlet and triplet states of organic diradicals. |
| PubMed:The lowest singlet states of octatetraene revisited. |
| PubMed:Surface-initiated ring-opening metathesis polymerization in the vapor phase: an efficient method for grafting cyclic olefins with low strain energies. |
| PubMed:Selective dilithiation of [Ti(η(5)-C5H5)(η(8)-C8H8)] and subsequent conversion into neutral and cationic ansa-complexes. |
| PubMed:Binuclear cyclopentadienylmetal cyclooctatetraene derivatives of the first row transition metals: effects of ring conformation on the bonding of an eight-membered carbocyclic ring to a pair of metal atoms. |
| PubMed:Synthesis of stable silicon heterocycles by reaction of organic substrates with a chlorosilylene [PhC(NtBu)2SiCl]. |
| PubMed:Control of postharvest Botrytis fruit rot of strawberry by volatile organic compounds of Candida intermedia. |
| PubMed:Cyclooctatetraene dianion--an artifact? |
| PubMed:Unusual electrocyclic rearrangements with group 14 element compounds: reversible isomerization of a π-aromatic digermyl complex with carbon-carbon and germanium-germanium multiple bond cleavage. |
| PubMed:Insights into the carbene-initiated aggregation of [Fe(cot)(2)]. |
| PubMed:Investigating the threshold of aromaticity and antiaromaticity by variation of nuclear charge. |
| PubMed:Formation of uranium(IV) oxide clusters from uranocene [U(eta(8)-C8H8)2] and uranyl [UO2X2] compounds. |
| PubMed:δ-Bonding in the [Pd4(μ4-C9H9)(μ4-C8H8)]+ sandwich complex. |
| PubMed:Studies on the reactivity of [Ge9]4- towards [Fe(cot)(CO)3]: synthesis and characterization of [Ge8Fe(CO)3]3- and of the anionic organometallic species [Fe(cot)(CO)3]-. |
| PubMed:New procedure to evaluate aromaticity at the density functional theory, Hartree-Fock, and post-self-consistent field levels. |
| PubMed:[4+2] cycloaddition reactions between 1,8-disubstituted cyclooctatetraenes and diazo dienophiles: stereoelectronic effects, anticancer properties and application to the synthesis of 7,8-substituted bicyclo[4.2.0]octa-2,4-dienes. |
| PubMed:Cleavage of the Sn-Sn multiple bond in a distannyne by cyclooctatetraene: formation of the pi-bound inverse sandwich complex [(Ar'Sn)2(mu2-eta2:eta3-cot)]. |
| PubMed:Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration. |
| PubMed:Spin-orbit effects on electronic delocalization. Aromaticity in a discrete square tetrapalladium sandwich complex. |
| PubMed:Cyclic tetrathiophenes planarized by silicon and sulfur bridges bearing antiaromatic cyclooctatetraene core: syntheses, structures, and properties. |
| PubMed:Synthesis of heteroleptic uranium (mu-eta(6):eta(6)-C6H6)2- sandwich complexes via facile displacement of (eta(5)-C5Me5)1- by ligands of lower hapticity and their conversion to heteroleptic bis(imido) compounds. |
| PubMed:Carbenes as catalysts for transformations of organometallic iron complexes. |
| PubMed:The synthesis of highly substituted cyclooctatetraene scaffolds by metal-catalyzed [2+2+2+2] cycloadditions: studies on regioselectivity, dynamic properties, and metal chelation. |
| PubMed:Square tetrapalladium sheet sandwich complexes: cyclononatetraenyl as a versatile face-capping ligand. |
| PubMed:Chiral crystallization: freezing a rapid Cope rearrangement in the solid state. |
| PubMed:Dynamic molecular tweezers composed of dibenzocyclooctatetraene units: synthesis, properties, and thermochromism in host-guest complexes. |
| PubMed:Cyclacenes: hoop-shaped systems composed of conjugated rings. |
| PubMed:Triplet excitation scavenging in films of conjugated polymers. |
| PubMed:Effect of intramolecular Paternò-Büchi reaction on the thermodynamics and kinetics of nearly degenerate [3,3]-sigmatropic shift in fluxional polycycles. |
| PubMed:Mitigating unwanted photophysical processes for improved single-molecule fluorescence imaging. |
| PubMed:Synthesis, properties and formation of (RCp)Co- and (RCp)Rh-stabilized[4.8]3cyclacene derivatives. |
| PubMed:Investigating metal size effects in the Ln2(mu-eta2:eta2-N2) reduction system: reductive reactivity with complexes of the largest and smallest trivalent lanthanide ions, La3+ and Lu3+. |
| PubMed:Computational investigation of hydrogen adsorption by alkali-metal-doped organic molecules: role of aromaticity. |
| PubMed:Photoelectron spectroscopic study of the anionic transition metalorganic complexes [Fe(1,2)(COT)](-) and [Co(COT)](-). |
| PubMed:Maps of current density using density-functional methods. |
| PubMed:Stacked-ring aromaticity: an orbital model. |
| PubMed:Aromaticity and antiaromaticity in the low-lying electronic states of cyclooctatetraene. |
| PubMed:High-pressure studies of 1,3,5,7-cyclooctatetraene: experiment and theory. |
| PubMed:Iridium-catalyzed asymmetric allylic substitutions--very high regioselectivity and air stability with a catalyst derived from dibenzo[a,e]cyclooctatetraene and a phosphoramidite. |
| PubMed:Accurate determination of the structure of cyclooctatetraene by femtosecond rotational coherence spectroscopy and ab initio calculations. |
| PubMed:Aromaticity and antiaromaticity in 4-, 6-, 8-, and 10-membered conjugated hydrocarbon rings. |
| PubMed:Electron-self-exchange kinetics of the cyclooctatetraene/cyclooctatetraene radical-anion couple. |
| PubMed:Ab initio structures for 90 degrees -twisted s-trans-1,3-butadiene and cyclooctatetraene: the naked sp2-sp2 bond. |
| PubMed:Very-low-lying electronic states result from n --> pi excitations in open-shell annulenes, annelated with alpha-dicarbonyl groups. |
| PubMed:Triplet-state aromaticity of 4npi-electron monocycles: analysis of bifurcation in the pi contribution to the electron localization function. |
| PubMed:Stern-gerlach study of multidecker lanthanide-cyclooctatetraene sandwich clusters. |
| PubMed:Antiaromaticity and reactivity of a planar cyclooctatetraene fully annelated with bicyclo[2.1.1]hexane units. |
| PubMed:Metal mediated synthesis of substituted cyclooctatetraenes. |
| PubMed:Experimental and theoretical investigations into the paratropic ring current of a porphyrin sheet. |
| PubMed:The role of the intersection space in the photochemistry of tricyclo[3.3.0.0(2,6)]octa-3,7-diene. |
| PubMed:Experimental/computational study of the electrochemical oxidation of cyclooctatetraene in protic media. Solvent effects. |
| PubMed:Full spectral decomposition of ring currents. |
| PubMed:Trivalent [(C5Me5)2(THF)Ln]2(mu-eta2:eta2-N2) complexes as reducing agents including the reductive homologation of CO to a ketene carboxylate, (mu-eta4-O2C-C=C=O)2-. |
| PubMed:Synthesis and biradicaloid character of doubly linked corrole dimers. |
| PubMed:C-H bond activation through steric crowding of normally inert ligands in the sterically crowded gadolinium and yttrium (C5Me5)3M complexes. |
| PubMed:Acetylene coupling on Cu(111): formation of butadiene, benzene, and cyclooctatetraene. |
| PubMed:Lanthanide organometallic sandwich nanowires: formation mechanism. |
| PubMed:CH stretching vibrational overtone spectra of 1,3,5,7-cyclooctatetraene and 1,1,1-trichloroethane. |
| PubMed:Geometric and electronic structures of multiple-decker one-end open sandwich clusters: Eu(n)(C8H8)n- (n = 1-4). |
| PubMed:Biradicals stabilized by intramolecular charge transfer: properties of heterosubstituted pentalene and cyclooctatetraene biradicals. |
| PubMed:A computational study of sulfur bridged cyclooctatetraenophanes. |
| PubMed:Persistence of paratropic ring currents in nonplanar, tub-shaped geometries of 1,3,5,7-cyclooctatetraene. |
| PubMed:Cobalt(I)-catalyzed [6+2] cycloadditions of cyclooctatetra(tri)ene with alkynes. |
| PubMed:A directly fused tetrameric porphyrin sheet and its anomalous electronic properties that arise from the planar cyclooctatetraene core. |
| PubMed:Yttrium and lanthanide complexes having a chiral phosphanylamide in the coordination sphere. |
| PubMed:Quantum chemical, ballistic and explosivity calculations on 2,4,6,8-tetranitro-1,3,5,7-tetraaza cyclooctatetraene: a new high energy molecule. |
| PubMed:Calcium, strontium, barium, and ytterbium complexes with cyclooctatetraenyl or cyclononatetraenyl ligands. |
| PubMed:Extraordinary cluster formation and intramolecular ligand-ligand interactions in cyanoacetylene [corrected] mediated by Mg+*: implications for the atmospheric chemistry of titan and for circumstellar chemistry. |
| PubMed:Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F. |
| PubMed:Synthesis, structure, and ligand-based reduction reactivity of trivalent organosamarium benzene chalcogenolate complexes (C(5)Me(5))(2)Sm(EPh)(THF) and [(C(5)Me(5))(2)Sm(mu-EPh)](2). |
| PubMed:Single-molecule nanosized polycyclic aromatics with alternant five- and six-membered rings: synthesis and optical properties. |
| PubMed:An organometallic synthesis of TiO2 nanoparticles. |
| PubMed:No-D NMR study of the pathway for n-BuLi "oxidation" of 1,5-cyclooctadiene to dilithium cyclooctatetraene dianion [Li2COT2-]. |
| PubMed:Polycyclooctatetraeneoxy alkane polyanionic polyradicals. |
| PubMed:Total synthesis of (+/-)-pentacycloanammoxic acid. |
| PubMed:Novel cyclooctatetraene radical cation planarized by full annelation with bicyclo[2.1.1]hexene units. |
| PubMed:A samarium cyclooctatetraene complex as catalyst for hydroamination/cyclisation catalysis. |
| PubMed:Structure, reactivity, and density functional theory analysis of the six-electron reductant, [(C5Me5)2U]2(mu-eta6:eta6-C6H6), synthesized via a new mode of (C5Me5)3M reactivity. |
| PubMed:Synthesis of 1,4-annulated cyclooctatetraenophanes based on a novel cubane building block approach. |
| PubMed:A theory of nonvertical triplet energy transfer in terms of accurate potential energy surfaces: the transfer reaction from pi,pi* triplet donors to 1,3,5,7-cyclooctatetraene. |
| PubMed:Caulerpin. |
| PubMed:Yttrium and lanthanide diphosphanylamides: syntheses and structures of complexes with one [(Ph2P)2N]- ligand in the coordination sphere. |
| PubMed:Mechanism of Reppe's nickel-catalyzed ethyne tetramerization to cyclooctatetraene: a DFT study. |
| PubMed:Synthesis, structure, and dynamics of nickelacarboranes incorporating the [nido-7,9-C(2)B(9)H(11)](2)(-) ligand. |
| PubMed:Reactions of sterically congested 1,5-hexadienes: Ab initio and DFT calculations on the competition between cope rearrangements and disrotatory cyclobutene ring-opening reactions of bridged syn-tricyclo[4.2.0.0(2,5)]octa-3,7-dienes. |
| PubMed:Reactivity of (bicyclo[5.1.0]octadienyl)iron(1+) cations: application to the synthesis of cis-2-(2'-carboxycyclopropyl)glycines. |
| PubMed:Diamagnetic and paramagnetic ring currents in expanded porphyrins. |
| PubMed:6a,6b,12a,12b-Tetrahydrocycloocta[3,4]cyclobuta[1,2][8]annulene. |
| PubMed:Remarkable reactions of cyclooctatetraene diiron-bridging carbyne complexes with amino and amido compounds: nucleophilic addition to and breaking of the cyclooctatetraene ring. |
| PubMed:The boratacyclooctatetraene ligand: an isoelectronic trianionic analogue of the cyclooctatetraene dianion. |
| PubMed:On the stability of large [4n]annulenes. |
| PubMed:Direct synthesis of soluble, end-functionalized polyenes and polyacetylene block copolymers. |
| PubMed:Interannular communication in the radical anions of bis-cyclooctatetraene systems. |
| PubMed:From hydrocarbons to polyols. Cyclooctatetraene to novel cyclooctitols. |
| PubMed:Mass spectral evidence of alkali metal insertion into C60-cyclooctatetraene complexes: M+@C60-C8H 8 *3-. |
| PubMed:Cyclooctatetraene computational photo- and thermal chemistry: a reactivity model for conjugated hydrocarbons. |
| PubMed:Tris(1-4-eta 4-anthracene)niobate(1-), the first polyaromatic hydrocarbon complex of niobium. |
| PubMed:About the Antiaromaticity of Planar Cyclooctatetraene I thank Jens Panitzky for the additional DFT calculations, and Professor Jay Siegel, La Jolla, CA, and Professor Otto Ermer, Cologne, for helpful comments. |
| PubMed:Density functional theory study of redox pairs: 2. Influence of solvation and ion-pair formation on the redox behavior of cyclooctatetraene and nitrobenzene. |
| PubMed:Tris(eta4-naphthalene)- and tris(1-4-eta4-anthracene)tantalate(1-): first homoleptic arene complexes of anionic tantalum. |
| PubMed:Diuranium inverted sandwiches involving naphthalene and cyclooctatetraene. |
| PubMed:Paratropic delocalized ring currents in flattened cyclooctatetraene systems with bond alternation. |
| PubMed:Role of bifurcation in the bond shifting of cyclooctatetraene. |
| PubMed:Ring currents in a proposed system containing planar hexacoordinate carbon, CB(2-)(6). |
| PubMed:Tunneling and sterically induced ring puckering in a substituted [8]annulene anion radical. |
| PubMed:A fresh look at aromatic dianions. |
| PubMed:Quantum mechanical investigation of the inner-sphere reorganization energy of cyclooctatetraene/cyclooctatetraene radical anion. Part I. |
| PubMed:Oxa bowls: studies toward hexaoxa-[6]-peristylane. Synthesis of a seco-derivative of hexaoxa-[6]-peristylane. |
| PubMed:A chemical definition of the effective reducing power of thulium(II) diiodide by its reactions with cyclic unsaturated hydrocarbons. |
| PubMed:The rearrangement of the cubane radical cation in solution. |
| PubMed:Efficient synthesis of benzene and planar cyclooctatetraene fully annelated with bicyclo[2.1.1]hex-2-ene. |
| PubMed:Quantum mechanical designs toward planar delocalized cyclooctatetraene: a new target for synthesis. |
| PubMed:Electronic structure of [(CpCr)[(CO)3M]]mu-Cot (M = Cr, Fe): a theoretical study. |
| PubMed:Chiral recognition between a substituted cyclooctatetraene dianion and a half crown ether substituted with ibuprofen. |
| PubMed:Nickel-catalyzed |
| PubMed:The Valence Isomerization of Cyclooctatetraene to Semibullvalene We are most grateful to "Servicios Informáticos de la Universidad de Alcalá", to Silicon Graphics, Inc. (Boston, MA) for computer facilities, and to Professors José-Luis Abboud (Instituto de Química Física "Rocasolano", C.S.I.C) and Julio Álvarez-Builla (Departamento de Química Organica, Universidad de Alcalá) for their generous and continuous support of our work. O.C. acknowledges financial support by the University of Alcalá for a short stay in the King's College, London, and the D.G.E.S. (project number PM97-0074). |
| PubMed:The radical cation of syn-tricyclooctadiene and its rearrangement products |
| PubMed:Unification of some literature models of aromaticity: calculational and conceptual study of a set of one-ring species. |
| PubMed:Thermolytic Behavior of 4-Fold Bridged syn-Tricyclo[4.2.0.0(2,5)]octa-3,7-dienes. |
| PubMed:Transition-State Spectroscopy of Cyclooctatetraene |
| PubMed:[Application of 2D-NMR techniques in the structure determination of hypodematine]. |
| PubMed:Thin Films of n-Si/Poly-(CH3)3Si-Cyclooctatetraene: Conducting-Polymer Solar Cells and Layered Structures. |
| PubMed:Cyclic polyolefins; synthesis of cyclooctatetraene from pseudopelletierine. |
| PubMed:Some isomers of amidone and related compounds. |
| PubMed:The synthesis of cycloöctatetraene from pseudopelletierine. |
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3D/inchi