82669

Sigma-Aldrich

1-Pyrenebutyric hydrazide

for fluorescence, ≥97.0% (T)

Synonym(s):
4-(1-Pyrenyl)butyric hydrazide
Empirical Formula (Hill Notation):
C20H18N2O
CAS Number:
Molecular Weight:
302.37
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

grade

for fluorescence

assay

≥97.0% (T)

mp

167-171 °C

SMILES string

NNC(=O)CCCc1ccc2ccc3cccc4ccc1c2c34

InChI

1S/C20H18N2O/c21-22-18(23)6-2-3-13-7-8-16-10-9-14-4-1-5-15-11-12-17(13)20(16)19(14)15/h1,4-5,7-12H,2-3,6,21H2,(H,22,23)

InChI key

SOPPDVMSOKMZOC-UHFFFAOYSA-N

General description

1-Pyrenebutyric hydrazide (PBH) finds biological/medical applications in the detection, labeling, and quantification of biological carbonyl compounds including aldehydes and/or ketones and carboxylic acids. It is also industrially used in chemo-sensor materials, lubricants, etc.

Application

1-Pyrenebutyric hydrazide may be used as a fluorescence derivatization reagent in the following:
  • Determination of succinylacetone (SA) in urine samples of hepatorenal tyrosinemia patients using high-pressure liquid chromatography with fluorescence detection (HPLC-FLD).
  • Determination of glutaric and 3-hydroxyglutaric acids in urine of glutaric acidemia type I patients using HPLC technique with intramolecular excimer-forming fluorescence derivatization.

Other Notes

Fluorescent labeling reagent for carbonyl compounds, e.g. cyclobutanones formed on food irradiation; Labeling of other compounds

Pictograms

Exclamation mark

Signal Word

Warning

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

J A Lee et al.
Biochemistry, 24(2), 322-330 (1985-01-15)
Sodium plus potassium activated adenosinetriphosphatase [(Na,K)ATPase] is composed of a catalytic subunit (alpha) and a glycoprotein subunit (beta) of unknown function. A method has been developed to label the beta subunit of purified dog kidney (Na,K)ATPase with fluorescent probes. The...
Fluorescent-labeled crosslinks in collagen: pyrenebutyrylhydrazine.
N Shambaugh et al.
Biopolymers, 21(1), 79-88 (1982-01-01)
Yuntao Zhang et al.
Journal of mass spectrometry : JMS, 43(6), 765-772 (2008-01-22)
In the present work, a rapid and novel method of on-target plate derivatization of keratan sulfate (KS) oligosaccharides for subsequent analysis by matrix-assisted laser desorption and ionization (MALDI) mass spectrometry is described. MALDI-(time-of-flight)-TOF spectra of labeled KS oligosaccharides revealed that...
Handbook of Fluorescent Dyes and Probes (2015)
Quantification of glutaric and 3-hydroxyglutaric acids in urine of glutaric acidemia type I patients by HPLC with intramolecular excimer-forming fluorescence derivatization
Al-Dirbashi YO, et al.
Clinica Chimica Acta; International Journal of Clinical Chemistry, 359(1-2), 179-188 (2005)

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