5-butylpyridine-2-carboxylic acid

• ChemBase ID: 102892
• Molecular Formular: C10H13NO2
• Molecular Mass: 179.21572
• Monoisotopic Mass: 179.09462866
• SMILES: CCCCc1cnc(cc1)C(=O)O
• Canonical SMILES: CCCCc1ccc(nc1)C(=O)O
• InChI: InChI=1S/C10H13NO2/c1-2-3-4-8-5-6-9(10(12)13)11-7-8/h5-7H,2-4H2,1H3,(H,12,13)
• InChIKey: DGMPVYSXXIOGJY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-butylpyridine-2-carboxylic acid
• IUPAC Traditional name: fusaric acid; 5-butylpyridine-2-carboxylic acid
• Synonyms: 5-Butylpicolinic acid; 5-Butylpyridine-2-carboxylic acid; FUSARIC ACID; Fusaric acid

Database IDs

• CAS Number: 536-69-6
• EC Number: 208-643-0
• MDL Number: MFCD00006298
• Beilstein Number: 125804
• PubChem SID: 24278183; 162089084
• PubChem CID: 3442

CALCULATED PROPERTIES

• Acid pKa: 1.1307683
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.9394941
• LogD (pH = 7.4): -0.32356936
• Log P: 1.0963559
• Molar Refractivity: 49.6295 cm^3
• Polarizability: 19.055037 Å^3
• Polar Surface Area: 50.19 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble50 mg/mL, clear, faintly yellow
• Melting Point: 96-100 °C

Safety Information

• Storage Condition: 0°C
• RTECS: US5625000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... DBH(1621)
• Mechanism of Action: Dopamine b-hydroxylase inhibitor

Product Information

• Purity: ≥99.0% (TLC)
• Biological Source: from Gibberella fujikuroi; Isol. from Fusarium lycopersici, Fusarium oxysporum, Fusarium vasinfectum and Gibberella fujikuroi
• Application(s): Antihypertensive; Plant growth inhibitor and insecticide
• Empirical Formula (Hill Notation): C10H13NO2

DETAILS

MP Biomedicals - 02105005

From Gibberella fujikuroi
Crystalline

Sigma Aldrich - F6513

Biochem/physiol Actions
Dopamine β-hydroxylase inhibitor.
包装
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 48205

Other Notes
Inhibits dopamine β-hydroxylase activity1

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn. , 1985, 2 , 786D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra , 1992, 3 , 319C, (nmr)
• Grove, F. et al. , J.C.S. , 1958, 1236, (isol) Chumakov, Y.I. et al. , Tet. Lett. , 1965, 129, (synth, ir)
• Vogt, H. et al. , Tet. Lett. , 1966, 5887, (synth)
• Tschesche, R. et al. , Chem. Ber. , 1978, 111 , 3502, (synth, spectra)
• Medvedeva, T.M.et al. , Khim.-Farm. Zh. , 1978, 12 , 66, (synth, pharmacol)
• Piesche, L. et al. , Pharmazie , 1979, 34 , 332, (pharmacol)
• Langhals, E. et al. , Annalen , 1982, 930, (synth) Schroetter, E. et al. , Pharmazie , 1984, 39 , 155, (synth)
• Sagi, M. et al. , Heterocycles , 1989, 29 , 2249, (synth)
• Waldner, A. , Synth. Commun. , 1989, 19 , 2371, (synth, pmr)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press , 1993, 841, (Fusaric acid)
• Koyama, J. et al. , Heterocycles , 1994, 38 , 1595, (synth)
• Renslo, A.R. et al. , J.O.C. , 1998, 63 , 7840-7850, (synth, Me ester, ir, pmr, cmr)
• Song,J.J. et al. , J.O.C. , 2001, 66 , 605-608, (synth)
• Lewis, R.J. , Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold , 1992, BSI000