6-{[(tert-butoxy)carbonyl]amino}hexanoic acid

• ChemBase ID: 38530
• Molecular Formular: C11H21NO4
• Molecular Mass: 231.28874
• Monoisotopic Mass: 231.14705816
• SMILES: C(CCCCC(=O)O)NC(=O)OC(C)(C)C
• Canonical SMILES: OC(=O)CCCCCNC(=O)OC(C)(C)C
• InChI: InChI=1S/C11H21NO4/c1-11(2,3)16-10(15)12-8-6-4-5-7-9(13)14/h4-8H2,1-3H3,(H,12,15)(H,13,14)
• InChIKey: RUFDYIJGNPVTAY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{[(tert-butoxy)carbonyl]amino}hexanoic acid
• IUPAC Traditional name: 6-[(tert-butoxycarbonyl)amino]hexanoic acid
• Synonyms: 6-(Boc-amino)caproic acid; 6-(Boc-amino)hexanoic acid; Boc-6-aminohexanoic acid; Boc-6-Ahx-OH; BOC-ε-aminocaproic Acid; N-(tert-Butoxycarbonyl)-6-aminocaproic Acid; N-(tert-Butoxycarbonyl)-6-aminohexanoic Acid; N-(tert-Butoxycarbonyl)-ε-aminocaproic Acid; N-(tert-Butoxycarbonyl)-ε-aminohexanoic Acid; N-(tert-Butyloxycarbonyl)-ε-aminocaproic Acid; tert-Butoxycarbonyl-ε-aminocaproic Acid; 6-[N-(tert-Butoxycarbonyl)amino]caproic Acid; Boc-6-Aminocaproic acid; Boc-6-aminohexanoic acid; 6-(Boc-氨基)羊油酸; Boc-6-氨基己酸; 叔丁氧羰酰基 6-氨基己酸

Database IDs

• CAS Number: 6404-29-1
• MDL Number: MFCD00037798
• Beilstein Number: 2049561
• PubChem SID: 161001837; 24849391
• PubChem CID: 637602

CALCULATED PROPERTIES

• Acid pKa: 4.190474
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.4317281
• LogD (pH = 7.4): -1.2804824
• Log P: 1.7594332
• Molar Refractivity: 59.5328 cm^3
• Polarizability: 23.466265 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 35-40 °C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (T); 95+%
• Linear Formula: (CH3)3CO2CNH(CH2)5CO2H

DETAILS

Sigma Aldrich - 15395

Other Notes
Protected derivative to introduce the ε-aminocaproyl moiety in various compounds.1,2 Introduction of an aminocaproyl spacer arm in affinity chromatography.3,4
Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - B690655

Protected ε-Aminocaproic Acid (A603015). Used in the preparatiom of esters of 6-aminohexanoic acid as antibacterial agents. EACA is reported to inhibit chymotrypsin, Factor VIIa, lysine carboxy peptidase, plasmin, and plasminogen activator.

REFERENCES

• Dolezal, P., et al.: Pharm. Res., 10, 1015 (1993)
• Vavrova, K., et al.: Curr. Med. Chem., 12, 2273 (1993)
• Holas, T., et al.: Bioorg. Med. Chem., 14, 7671 (1993)