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Sigma-Aldrich

Pyrene

puriss. p.a., for fluorescence, ≥99.0% (GC)

Synonym(s):

Benzo[def]phenanthrene

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About This Item

Empirical Formula (Hill Notation):
C16H10
CAS Number:
129-00-0
Molecular Weight:
202.25
Beilstein:
1307225
EC Number:
204-927-3
MDL number:
MFCD00004136
UNSPSC Code:
12171500
PubChem Substance ID:
57652921
NACRES:
NA.32

grade

for fluorescence
puriss. p.a.

Assay

≥99.0% (GC)

form

crystals

mp

145-148 °C (lit.)
151-154 °C

solubility

ethanol: soluble

cation traces

Ca: ≤50 mg/kg
Cd: ≤50 mg/kg
Co: ≤50 mg/kg
Cr: ≤50 mg/kg
Cu: ≤50 mg/kg
Fe: ≤50 mg/kg
K: ≤50 mg/kg
Mg: ≤50 mg/kg
Mn: ≤50 mg/kg
Na: ≤50 mg/kg
Ni: ≤50 mg/kg
Pb: ≤50 mg/kg
Zn: ≤50 mg/kg

fluorescence

λex 338 nm; λem 375 nm in DMSO

SMILES string

c1cc2ccc3cccc4ccc(c1)c2c34

InChI

1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H

InChI key

BBEAQIROQSPTKN-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

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Analysis Note

In addition to the emission maximum at 375 nm, there are lower maxima at 395, 385, 380, 415 and 445 nm.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

435.2 °F

Flash Point(C)

224 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yan Fang et al.
Drug delivery, 23(9), 3582-3593 (2016-09-30)
A kind of polymeric lipid vesicles (PLVs) with pH-responsive turning on-off membrane for programed delivery of insulin in gastrointestinal (GI) tract was developed, which was self-assembled from the grafted amphipathic polymer of N-tocopheryl-N'-succinyl-ɛ-poly-l-lysine (TP/SC-g-PLL). By controlling the grafting ratio of
Pentti Somerharju
Chemistry and physics of lipids, 116(1-2), 57-74 (2002-07-03)
Pyrene is one of the most frequently used lipid-linked fluorophores. Its most characteristic features are a long excited state lifetime and (local) concentration-dependent formation of excimers. Pyrene is also hydrophobic and thus does not significantly distort the conformation of the
Michael E Østergaard et al.
Chemical Society reviews, 40(12), 5771-5788 (2011-04-14)
Pyrene-functionalized oligonucleotides (PFOs) are increasingly explored as tools in fundamental research, diagnostics and nanotechnology. Their popularity is linked to the ability of pyrenes to function as polarity-sensitive and quenchable fluorophores, excimer-generating units, aromatic stacking moieties and nucleic acid duplex intercalators.
Intramolecular pyrene excimer fluorescence: a probe of proximity and protein conformational change.
S S Lehrer
Methods in enzymology, 278, 286-295 (1997-01-01)
Tomohiro Kato et al.
Journal of the American Chemical Society, 135(2), 741-750 (2012-12-18)
Although distance dependence of Förster resonance energy transfer (FRET) is well-studied and FRET has been extensively applied as "molecular ruler", only limited examples of orientation-dependent FRET have been reported. To create a robust FRET system that precisely reflects the orientation
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