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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

Related Categories

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
Kentaro Misaki et al.
Mutagenesis, 23(5), 359-366 (2008-05-16)
1H-Phenalen-1-one (phenalenone) is one of the major oxygenated polyaromatic compounds present in the atmospheric environment. In order to gain detailed information regarding the mutagenicity and physicochemical properties of the nitration products of phenalenone, we measured Ames Salmonella mutagenicity, lower LUMO
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
Stefan Opitz et al.
Journal of natural products, 65(8), 1122-1130 (2002-08-24)
Phytochemical analysis of Xiphidium caeruleum, a neotropical member of the family Haemodoraceae, resulted in the isolation and identification of a variety of phenylphenalenone-related compounds. The structures of four new phenylbenzoisochromenones (3, 6, 7, 10), a new phenylbenzoisoquinolinone (4), and two
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