6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanoic acid

• ChemBase ID: 155817
• Molecular Formular: C12H14N4O5
• Molecular Mass: 294.26336
• Monoisotopic Mass: 294.09641957
• SMILES: c1cc(c2c(c1NCCCCCC(=O)O)non2)[N+](=O)[O-]
• Canonical SMILES: OC(=O)CCCCCNc1ccc(c2c1non2)[N+](=O)[O-]
• InChI: InChI=1S/C12H14N4O5/c17-10(18)4-2-1-3-7-13-8-5-6-9(16(19)20)12-11(8)14-21-15-12/h5-6,13H,1-4,7H2,(H,17,18)
• InChIKey: DJFNQJJTTPMBIL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanoic acid
• IUPAC Traditional name: nbd-X
• Synonyms: 6-(7-Nitro-2,1,3-benzoxadiazol-4-ylamino)hexanoic acid; 6-(7-Nitrobenzofurazan-4-ylamino)hexanoic acid; 6-[(7-Nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanoic Acid; 6-[(7-Nitrobenzofurazan-4-yl)amino]hexanoic Acid; 6-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]hexanoic Acid; C6-NBD; N316; NBD-X; NBD Hexanoic Acid

Database IDs

• CAS Number: 88235-25-0
• MDL Number: MFCD00057884
• Beilstein Number: 6936249
• PubChem SID: 162249955
• PubChem CID: 139072

CALCULATED PROPERTIES

• Acid pKa: 4.315514
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.41878653
• LogD (pH = 7.4): -1.3228195
• Log P: 1.6288254
• Molar Refractivity: 74.3943 cm^3
• Polarizability: 27.679821 Å^3
• Polar Surface Area: 134.07 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Fluorescence: λex 466 nm; λem 535 nm in methanol

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Product Information

• Purity: ≥96.0% (HPLC)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C12H14N4O5

DETAILS

Sigma Aldrich - 72964

Other Notes
Probing of the binding sites of fatty acid and sterol carrier proteins1

Toronto Research Chemicals - N381280

NBD Hexanoic Acid is used as a fluorescent probes for studying the fat globule (membrane) of bovine and human.

REFERENCES

• Greenough, K.OP. et al.: J. Phys. Chem. B, 110, 6351 (2006)
• Evers, J.M. et al.: Milchwissenschaft, 63, 402 (2006)
• Huang, H. et al.: J. Biol. Chem., 277, 29139 (2006)