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764396 Sigma-Aldrich

(E)-Cyclooct-4-enol

Synonym: (4E)-4-Cycloocten-1-ol, trans-Cyclooctenol, TCO-OH, rel-(1R,4E,pR)-Cyclooct-4-enol

  • CAS Number 85081-69-2

  • Empirical Formula (Hill Notation) C8H14O

  • Molecular Weight 126.20

  •  PubChem Substance ID 329767115

  •  NACRES NA.22

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper-Free Click Chemistry, Tetrazine/Strained-alkene Click Chemistry Reagents More...
storage temp.   −20°C
SMILES string   O[C@@H]1CCC\C=C\CC1
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

Description

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.

Packaging

10, 50 mg in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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