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P10801

Sigma-Aldrich

Perinaphthenone

97%

Synonym(s):

1H-Benzonaphthen-1-one, 7-Perinaphthenone, Phenalenone, Phenalone

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About This Item

Empirical Formula (Hill Notation):
C13H8O
CAS Number:
548-39-0
Molecular Weight:
180.20
EC Number:
208-945-2
MDL number:
MFCD00004143
UNSPSC Code:
12352100
PubChem Substance ID:
24898151
NACRES:
NA.22

Quality Level

100

Assay

97%

form

powder

mp

153-156 °C (lit.)

SMILES string

O=C1C=Cc2cccc3cccc1c23

InChI

1S/C13H8O/c14-12-8-7-10-4-1-3-9-5-2-6-11(12)13(9)10/h1-8H

InChI key

WWBGWPHHLRSTFI-UHFFFAOYSA-N

Application

Perinaphthenone can be used:
  • In the Weitz-Scheffer epoxidation to produce the corresponding epoxides in the presence of gem-dihydroperoxide as the stoichiometric oxidant.
  • As a photosensitizer in the photodegradation of tebuconazole.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM6374
BCCK7418
BCCJ4965
BCCK3980
STBH9725

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William Hidalgo et al.
Journal of agricultural and food chemistry, 57(16), 7417-7421 (2009-07-28)
The levels of native fungitoxic perinaphthenone phytoalexins in susceptible Musa varieties (banana), which are commercially grown in large plantations, are too low to provide plants with long-lasting protection against highly pathogenic fungi. Novel strategies for plant protection are necessary to
Cristina Flors et al.
Accounts of chemical research, 39(5), 293-300 (2006-05-17)
Plants defend themselves from pathogen infections or mechanical injury by a number of mechanisms, including the induced biosynthesis of antimicrobial secondary metabolites. These compounds, termed phytoalexins, represent a very economical way to counteract hazard, because the carbon and energy resources
S Opitz et al.
Planta, 216(5), 881-889 (2003-03-08)
Phenylphenalenones represent a typical group of secondary metabolites of the Haemodoraceae. Some of these phenolic compounds show organ-specific distribution within the plant. However, detailed information on cellular localisation is still lacking. To this end, confocal laser-scanning microscopy, microspectral photometry and
Xiaopeng Chen et al.
Chemical communications (Cambridge, England), 47(9), 2628-2630 (2011-01-15)
Phenalenone derivatives were efficiently constructed from 1,8-diiodonaphthalene and tertiary propynols via a one-pot domino reaction which eventually included Pd-catalyzed Sonogoshira coupling, Pd-catalyzed allylic oxidation and Pd-catalyzed C(sp(2))-H activation. Moreover, the synthesized phenalenone derivative presented a practical application as a fluorescent
Felipe Otálvaro et al.
Journal of natural products, 70(5), 887-890 (2007-04-13)
Two perinaphthenone-type compounds (1 and 2) were isolated together with four known phenylphenalenones (3-6) from the rhizomes of Musa acuminata var. "Yangambi km 5". The structures of the new phenalenones were assigned as 2-hydroxy-1H-phenalen-1-one (1) and 2-methoxy-1H-phenalen-1-one (2) on the
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