norcarane
Identification
| Name | norcarane |
| IUPAC | bicyclo[4.1.0]heptane |
| CAS Number | 286-08-8 |
| FDA UNII | ZGC3T0R48Q |
| Molecular Formula | C7 H12 |
| Molecular Weight | 96.17264000 |
| Nikkaji Number | J10.624K |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 42.86 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 norcarane usage levels up to | not for fragrance use. |
| Recommendation for norcarane flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
bicyclo(4.1.0)heptane
bicyclo[4.1.0]heptane
1,2-
methylene cyclohexane
1,2-
methylenecyclohexane
PubMed:
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Manganese Catalyzed C-H Halogenation.
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Solution structures of lithium amino alkoxides used in highly enantioselective 1,2-additions.
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Identity and mechanisms of alkane-oxidizing metalloenzymes from deep-sea hydrothermal vents.
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Substrate specificity and reaction mechanism of purified alkane hydroxylase from the hydrocarbonoclastic bacterium Alcanivorax borkumensis (AbAlkB).
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Parallel and competitive pathways for substrate desaturation, hydroxylation, and radical rearrangement by the non-heme diiron hydroxylase AlkB.
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Selective hydroxylation of alkanes by an extracellular fungal peroxygenase.
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Manganese porphyrins catalyze selective C-H bond halogenations.
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The effect of a complexed lithium cation on a norcarane-based radical clock.
PubMed:
Profiling mechanisms of alkane hydroxylase activity in vivo using the diagnostic substrate norcarane.
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Products from enzyme-catalyzed oxidations of norcarenes.
PubMed:
Desaturase reactions complicate the use of norcarane as a mechanistic probe. Unraveling the mixture of twenty-plus products formed in enzyme-catalyzed oxidations of norcarane.
PubMed:
Oxygen-18 tracer studies of enzyme reactions with radical/cation diagnostic probes.
PubMed:
Reaction mechanisms of non-heme diiron hydroxylases characterized in whole cells.
PubMed:
Remarkable aliphatic hydroxylation by the diiron enzyme toluene 4-monooxygenase in reactions with radical or cation diagnostic probes norcarane, 1,1-dimethylcyclopropane, and 1,1-diethylcyclopropane.
PubMed:
endo/exo isomerism in norcarane and 2-norcaranol hydrotrioxides (ROOOH).
PubMed:
Xylene monooxygenase, a membrane-spanning non-heme diiron enzyme that hydroxylates hydrocarbons via a substrate radical intermediate.
PubMed:
Evaluation of norcarane as a probe for radicals in cytochome p450- and soluble methane monooxygenase-catalyzed hydroxylation reactions.
PubMed:
Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane.
PubMed:
Intermediate Q from soluble methane monooxygenase hydroxylates the mechanistic substrate probe norcarane: evidence for a stepwise reaction.
PubMed:
Electronic and steric factors in regioselective hydroxylation catalyzed by purified cytochrome P-450.