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
form
liquid
reaction suitability
reaction type: click chemistry
reagent type: linker
functional group
hydroxyl
storage temp.
−20°C
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
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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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)
Development of a novel antibody?tetrazine conjugate for bioorthogonal pretargeting.
Maggi A, et al.
Organic & Biomolecular Chemistry, 14(31), 7544-7551 (2016)
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)
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