764396
(E)-Cyclooct-4-enol
Synonym(s):
(4E)-4-Cycloocten-1-ol, trans-Cyclooctenol, TCO-OH, rel-(1R,4E,pR)-Cyclooct-4-enol
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About This Item
Empirical Formula (Hill Notation):
C8H14O
CAS Number:
Molecular Weight:
126.20
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22
SMILES string
O[C@H]1CC/C=C/CCC1
InChI
1S/C8H14O/c9-8-6-4-2-1-3-5-7-8/h1-2,8-9H,3-7H2/b2-1+/t8-/m0/s1
InChI key
UCPDHOTYYDHPEN-CMLYIYFCSA-N
form
liquid
reaction suitability
reaction type: click chemistry
reagent type: linker
functional group
hydroxyl
storage temp.
−20°C
Quality Level
Application
(E)-Cyclooct-4-enol may be used in the multi-step synthesis of trans-cyclooctene geranyl diphosphate, a novel strained-ring containing protein farnesyltransferase (PFTase) substrate that can be used in site-specific modification technologies.
Hydroxyl modified cyclooctene derivative. Cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1,2,4,5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Site?Specific Labeling of Proteins and Peptides with Trans?cyclooctene Containing Handles Capable of Tetrazine Ligation
Wollack JW, et al.
Chemical Biology & Drug Design, 84(2), 140-147 (2014)
Synthesis, characterization and radiolabeling of carborane-functionalized tetrazines for use in inverse electron demand Diels?Alder ligation reactions.
Genady AR, et al.
Journal of Organometallic Chemistry, 791, 204-213 (2015)
Click to release: instantaneous doxorubicin elimination upon tetrazine ligation.
Versteegen RM, et al.
Angewandte Chemie (International Edition in English), 52(52), 14112-14116 (2013)
A 99mTc-Labelled Tetrazine for Bioorthogonal Chemistry. Synthesis and Biodistribution Studies with Small Molecule trans-Cyclooctene Derivatives.
Vito A, et al.
PLoS ONE, 11(12), e0167425-e0167425 (2016)
Reprint of: Synthesis, characterization and radiolabeling of carborane-functionalized tetrazines for use in inverse electron demand Diels?Alder ligation reactions.
Genady AR, et al.
Journal of Organometallic Chemistry, 798, 278-288 (2015)
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