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Merck
CN

145017

3-Penten-2-one

70%

Synonym(s):

Methyl propenyl ketone

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About This Item

Linear Formula:
CH3CH=CHCOCH3
CAS Number:
625-33-2
Molecular Weight:
84.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848542
EC Number:
210-888-3
Beilstein/REAXYS Number:
1633505
MDL number:
MFCD00009290
Assay:
70%
Form:
liquid

Key Documents

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Product Name

3-Penten-2-one, 70%

InChI

1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3

InChI key

LABTWGUMFABVFG-UHFFFAOYSA-N

SMILES string

CC(C=CC)=O

vapor pressure

760 mmHg ( 121 °C)

assay

70%

form

liquid

impurities

<2% ethanol
30% mesityl oxide

refractive index

n20/D 1.437 (lit.)

bp

121-124 °C (lit.)

density

0.862 g/mL at 25 °C (lit.)

functional group

ketone

Quality Level

100

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Application

3-Penten-2-one was used in the synthesis of the alkaloids (+/-)-senepodine G and (+/-)-cermizine C.

Biochem/physiol Actions

3-Penten-2-one inhibits nitric oxide production and inducible nitric oxide synthase expression via heme oxygenase-1 expression in lipopolysaccharide-activated RAW264.7 macrophages.

General description

3-Penten-2-one is volatile compound present in berry fruit of two Aronia melanocarpa genotypes. Urinary 3-penten-2-one is a useful biomarker for increased accumulation of acetaldehyde during abnormal metabolic stress.

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

69.8 °F - closed cup

flash_point_c

21 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
0000499475
0000499475
0000472803
0000472803
0000472802

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Valerie Walker et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(8-9), 784-790 (2009-02-28)
Diagnostic profiling of urine for volatile compounds of around 400 patients using headspace solid-phase microextraction (HS-SPME) in alkaline conditions identified 3-penten-2-one (approximately 1 to >6.3 micromol/L) in 26 patients. Five were in barbiturate coma. 3-Penten-2-one, previously of unknown origin, was
Douglass F Taber et al.
The Journal of organic chemistry, 75(16), 5737-5739 (2010-08-14)
Preparatively useful conjugate addition of lithiated methyl pyridines to cyclic and acyclic enones is reported. Addition of 2-picoline to 3-penten-2-one led to a concise synthesis of the alkaloids (+/-)-senepodine G and (+/-)-cermizine C.
Jin-Sang Kil et al.
Journal of clinical biochemistry and nutrition, 50(1), 53-58 (2012-01-17)
Excess production of nitric oxide by activated macrophages via inducible nitric oxide synthase leads to the development of various inflammatory diseases. Heme oxygenase-1 expression via activation of nuclear factor-erythroid 2-related factor 2 inhibits nitric oxide production and inducible nitric oxide
Akiko Fujita et al.
Scientific reports, 9(1), 10586-10586 (2019-07-25)
Epilepsy is a chronic neurological disorder affecting mammals, including humans. Uncontrolled epilepsy is associated with poor quality of life, accidents, and sudden death. In particular, temporal lobe epilepsy (TLE) is the most common type of pharmacoresistant epilepsy, which easily gets
Vilma Kraujalytė et al.
Journal of agricultural and food chemistry, 61(20), 4728-4736 (2013-05-15)
The profiles of volatile constituents of berry fruit of two Aronia melanocarpa genotypes were evaluated by headspace-solid-phase microextraction (HS-SPME), simultaneous distillation and extraction (SDE), and gas chromatography-olfactometry (GC-O). In total, 74 volatile compounds were identified in chokeberry juice, 3-penten-2-one, 3,9-epoxy-p-menth-1-ene
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