764396

(E)-Cyclooct-4-enol

• Synonym(s): (4E)-4-Cycloocten-1-ol, trans-Cyclooctenol, TCO-OH, rel-(1R,4E,pR)-Cyclooct-4-enol
• Empirical Formula (Hill Notation): C₈H₁₄O
• CAS Number: 85081-69-2
• Molecular Weight: 126.20
• UNSPSC Code: 12352200
• PubChem Substance ID: 329767115
• NACRES: NA.22

Properties

• 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

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.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H318
• Precautionary Statements: P280 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable