Azobenzene
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Azobenzene can be used as an optical trigger for the design and synthesis of a large variety of photoresponsive systems.
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- Pureté: 98.0%
- CAS No.: 103-33-3
- Formule: C12H10N2
- Masse moléculaire:182.22
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Stockage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Pureté et documentation
- Références
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Help & FAQs
Activité biologique
Description
In Vitro
Photochromic compounds that undergo large conformational changes when exposed to light of appropriate wavelength are particularly attractive as molecular switch elements. Azobenzene is a popular choice among the chromophores. The thermodynamically favored trans isomer is rapidly converted to the cis isomer by irradiation at the wavelength of the π-π* transition, whereas the reverse process is achieved either (slowly) by thermal relaxation in the dark or (quickly) by irradiation at the wavelength of the n-π* transition. The azobenzene amino acid (aa) can be used as a photo-inducible conformational switch in polypeptides. A reversible conformational change of the peptide backbone is induced by switching between the cis and trans configurations of the azobenzene moiety by irradiation with light of suitable wavelength[1]. Azobenzene has been the most widely used optical trigger for the synthesis of photoresponsive systems ranging from poly-a-amino acids to innovative materials with light-controlled mechanical and optical properties. Its use in form of appropriate derivatives allow to generate cyclic peptide structures of constraint conformational space and thus to exploit its reversible photoisomerization to induce well defined transitions between different conformational states[2]. Azobenzene photoswitches can be used to drive functional changes in peptides, proteins, nucleic acids, lipids, and carbohydrates[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 103-33-3
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Appearance Solid
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Masse moléculaire 182.22
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Formule C12H10N2
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Color Yellow to orange
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SMILES
C1(/N=N/C2=CC=CC=C2)=CC=CC=C1
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 2 years -20°C 1 year
Solvant et solubilité
In Vitro:
DMSO : ≥ 150 mg/mL (823.18 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
* "≥" means soluble, but saturation unknown.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pureté et documentation
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Fiche technique (272 KB)
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SDS (761 KB)
- English - EN (761 KB)
- Français - FR (761 KB)
- Deutsch - DE (761 KB)
- Norwegian - NO (761 KB)
- Español - ES (761 KB)
- Swedish - SV (761 KB)
- Italian - IT (761 KB)
- Korean - KR (761 KB)
- Portuguese - PT (761 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. Aemissegger A, et al. Synthesis and application of an azobenzene amino acid as a light-switchable turn element in polypeptides. Nat Protoc. 2007;2(1):161-7. [Content Brief]
[2]. Renner C, et al. Azobenzene as photoresponsive conformational switch in cyclic peptides. J Pept Res. 2005 Jan;65(1):4-14. [Content Brief]
[3]. Beharry AA, et al. Azobenzene photoswitches for biomolecules. Chem Soc Rev. 2011 Aug;40(8):4422-37. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 5.4879 mL | 27.4394 mL | 54.8787 mL | 137.1968 mL |
| 5 mM | 1.0976 mL | 5.4879 mL | 10.9757 mL | 27.4394 mL | |
| 10 mM | 0.5488 mL | 2.7439 mL | 5.4879 mL | 13.7197 mL | |
| 15 mM | 0.3659 mL | 1.8293 mL | 3.6586 mL | 9.1465 mL | |
| 20 mM | 0.2744 mL | 1.3720 mL | 2.7439 mL | 6.8598 mL | |
| 25 mM | 0.2195 mL | 1.0976 mL | 2.1951 mL | 5.4879 mL | |
| 30 mM | 0.1829 mL | 0.9146 mL | 1.8293 mL | 4.5732 mL | |
| 40 mM | 0.1372 mL | 0.6860 mL | 1.3720 mL | 3.4299 mL | |
| 50 mM | 0.1098 mL | 0.5488 mL | 1.0976 mL | 2.7439 mL | |
| 60 mM | 0.0915 mL | 0.4573 mL | 0.9146 mL | 2.2866 mL | |
| 80 mM | 0.0686 mL | 0.3430 mL | 0.6860 mL | 1.7150 mL | |
| 100 mM | 0.0549 mL | 0.2744 mL | 0.5488 mL | 1.3720 mL |
Azobenzene Related Classifications
HY-B2127 Related Classifications
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