ol

• ChemBase ID: 146531
• Molecular Formular: C9H16NO3
• Molecular Mass: 186.22824
• Monoisotopic Mass: 186.11301838
• SMILES: CC1(CC(C(N1[O])(C)C)C(=O)O)C
• Canonical SMILES: OC(=O)C1CC(N(C1(C)C)[O])(C)C
• InChI: InChI=1S/C9H16NO3/c1-8(2)5-6(7(11)12)9(3,4)10(8)13/h6H,5H2,1-4H3,(H,11,12)
• InChIKey: GEPIUTWNBHBHIO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ol
• IUPAC Traditional name: tyrosine(.)
• Synonyms: 2,2,5,5-Tetramethyl-3-carboxypyrrolidine-N-oxyl; 3-Carboxy-PROXYL; DL-3-Carboxy-2,2,5,5-tetramethyl-1-pyrrolidinyloxyl; NSC 158842; PCA; 3-Carboxy-2,2,5,5-tetramethylpyrrolidinyl-1-oxy; 3-(Carboxy)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy; 3-Carboxy-2,2,5,5-tetramethyl-1-pyrrolidinyloxy, free radical; 3-Carboxy-PROXYL; 3-Carboxy-PROXYL, free radical; 3-(羧基)-2,2,5,5-四甲基-1-吡咯烷基氧基; 3-羧基-2,2,5,5-四甲基-1-吡咯烷基氧自由基; 3-羧基-PROXYL; 3-羧基-PROXYL, 自由基

Database IDs

• CAS Number: 2154-68-9
• EC Number: 218-448-2
• MDL Number: MFCD00003167
• Beilstein Number: 4136411
• PubChem SID: 24855305; 162240725
• PubChem CID: 519874

CALCULATED PROPERTIES

• Acid pKa: 4.519
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.33391616
• LogD (pH = 7.4): -2.104542
• Log P: 0.68901193
• Molar Refractivity: 47.0772 cm^3
• Polarizability: 18.857664 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: Yellow Solid
• Melting Point: 194-197°C; 200 °C (dec.)(lit.); ca 200°C dec.

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: UY6705500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C9H16NO3

DETAILS

Sigma Aldrich - 253324

Application
Spin-label that has been used to study molecular migration and long-term stability of seeds and pollen. Has been covalently attached to oligonucleotides to prepare a DNA probe sensitive to electron spin resonance. The acetoxymethyl ester is an esterase-sensitive probe that crosses the blood-brain barrier for electron spin resonance-computed tomographic imaging.
Spin-label. The anionic form has been used to determine distribution coefficients of neutral solubilizates in anionic micelles.
Used in the preparation of a tetraphenylporphyrin bearing a nitroxyl radical.
Packaging
1 g in glass bottle

Toronto Research Chemicals - C182770

The anionic form has been used to determine distribution coefficients of neutral solubilizates in anionic micelles.

REFERENCES

• Reviews: Synthesis and reactions of stable nitroxyl radicals: Synthesis, 190, 401 (1971); Advances in the chemistry of nitroxide spin labels: Chem. Rev., 78, 37 (1978); Recent advances in the chemistry of nitroxides and their applications in spin labelling: J. Sci. Ind. Res., 54, 623 (1995).