3-penten-2-one

Structural formula
	Structural formula of the (E) isomer
General
Surname	3-penten-2-one
other names	Methyl propenyl ketone; Ethylidene acetone;
Molecular formula	C 5 H 8 O
Brief description	colorless liquid
External identifiers / databases
EC number	210-888-3
ECHA InfoCard	100.009.899
Wikidata	Q64774214
properties
Molar mass	84.12 g mol −1
Physical state	liquid
density	0.861 g cm −3 ; 0.862 g cm −3 ( E );
boiling point	121-124 ° C; 109 ° C ( E );
solubility	soluble in water, acetone and ether ( E )
Refractive index	1.4355 (20 ° C)
safety instructions
H and P phrases	H: 225-311-315-319-335
	P: 210-280-302 + 352 + 312-305 + 351 + 338-370 + 378-403 + 235
Toxicological data	3200 mg kg −1 ( LD 50 , rat , oral ) ; 431 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

3-penten-2-one is a chemical compound from the group of ketones that occurs in two stereoisomeric forms.

Isomers

3-penten-2-one can have ( E ) - or ( Z ) -configuration at the double bond , consequently there are two isomers of the substance.

Isomers of 3-penten-2-one
Surname	( E ) -3-penten-2-one	( Z ) -3-penten-2-one
other names	trans -3-penten-2-one	cis -3-penten-2-one
Structural formula
CAS number	3102-33-8	3102-32-7
	625-33-2 (unspec.)
EC number	-	-
	210-888-3 (unspec.)
ECHA info card	-	-
	100.009.899 (unspec.)
PubChem	637920	5356572
	- (unspec.)
Wikidata	Q27161739	Q27292477
	Q64774214 (unspec.)

Occurrence

3-penten-2-one occurs naturally in the berries of two types of aronia melanocarpa . It has also been found in various other plants and foods such as tomatoes, cocoa, tea and potato chips.

Extraction and presentation

3-penten-2-one can be obtained by reacting 4-hydroxy-pentan-2-one with oxalic acid .

properties

3-penten-2-one is a colorless liquid with a fruity to pungent odor.

use

3-Penten-2-one can be used to synthesize other chemical compounds such as the alkaloids Senepodin G and Cermizin C. It is also used as a flavoring agent.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 3-penten-2-one in the GESTIS substance database of the IFA , accessed on July 25, 2017(JavaScript required) .
^ ^A ^b Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 72 ( limited preview in Google Book search).
^ William M. Haynes: CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 440 ( limited preview in Google Book Search).
↑ ^a ^b ^c ^d data sheet 3-Penten-2-one, tech. 85% at AlfaAesar, accessed July 25, 2017 ( PDF )(JavaScript required) .
↑ ^a ^b Data sheet 3-Penten-2-one, 70% from Sigma-Aldrich , accessed on July 25, 2017 ( PDF ).
↑ ^a ^b ^c ^d George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9414-0 , pp. 2997 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 3-penten-2-one in the GESTIS substance database of the IFA , accessed on July 25, 2017(JavaScript required) .

[Carl_L._Yaws-2] A ^b Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 72 ( limited preview in Google Book search).

[William_M._Haynes-3] William M. Haynes: CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 440 ( limited preview in Google Book Search).

[Alfa-4] ta sheet 3-Penten-2-one, tech. 85% at AlfaAesar, accessed July 25, 2017 ( PDF )(JavaScript required) .

[Sigma-5] Data sheet 3-Penten-2-one, 70% from Sigma-Aldrich , accessed on July 25, 2017 ( PDF ).

[George_A._Burdock-6] George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9414-0 , pp. 2997 ( limited preview in Google Book search).