Levulinic acid

Structural formula
General
Surname	Levulinic acid
other names	Levulinic acid; Levulinic acid; 4-oxopentanoic acid; 4-oxovaleric acid; LEVULINIC ACID ( INCI ) ;
Molecular formula	C 5 H 8 O 3
Brief description	colorless to yellowish solid
External identifiers / databases
EC number	204-649-2
ECHA InfoCard	100.004.228
PubChem	11579
ChemSpider	11091
DrugBank	DB02239
Wikidata	Q903322
properties
Molar mass	116.11 g mol −1
Physical state	firmly
density	1.13 g cm −3
Melting point	33-35 ° C
boiling point	244-246 ° C
solubility	good in water (675 g l −1 at 25 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319
	P: 260-302 + 352-305 + 351 + 338
Toxicological data	1850 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 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 .

The levulinic acid (also 4-oxopentanoic acid or 4-oxovaleric acid ) is a chemical compound belonging to the γ-keto acids is one and the same time represents the simplest representative.

Extraction and presentation

Levulinic acid can be produced in high yield from hexoses such as glucose or fructose by boiling with hydrochloric acid . In addition, levulinic acid can be obtained by hydrolysis of cellulose can be obtained.

use

Levulinic acid is used in textile printing and as a synthesis component in organic syntheses.

Levulinic acid can be used as a bio-based platform chemical . A first practical application are levulinic acid ketals .

In biochemistry , δ-aminolevulinate , a derivative of levulinic acid, is an intermediate product of porphyrin biosynthesis .

Individual evidence

↑ Entry on LEVULINIC ACID in the CosIng database of the EU Commission, accessed on July 2, 2020.
↑ ^a ^b ^c ^d ^e ^f data sheet levulinic acid (PDF) from Carl Roth , accessed on February 9, 2008.
↑ ^a ^b ^c Data sheet levulinic acid (PDF) from Merck , accessed on April 8, 2011.
↑ ^a ^b Entry on 4-oxopentanoic acid. In: Römpp Online . Georg Thieme Verlag, accessed on August 19, 2015.
^ Joseph J. Bozell, Gene R. Petersen: Technology development for the production of biobased products from biorefinery carbohydrates — the US Department of Energy's “Top 10” revisited . In: Green Chemistry . tape 12 , no. January 4 , 2010, doi : 10.1039 / b922014c .

↑ Segetis Technology ( Memento of the original from September 12, 2015 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2

[CosIng-1] Entry on LEVULINIC ACID in the CosIng database of the EU Commission, accessed on July 2, 2020.

[Roth-2] ↑ ^a ^b ^c ^d ^e ^f data sheet levulinic acid (PDF) from Carl Roth , accessed on February 9, 2008.

[Merck-3] Data sheet levulinic acid (PDF) from Merck , accessed on April 8, 2011.

[roempp-4] Entry on 4-oxopentanoic acid. In: Römpp Online . Georg Thieme Verlag, accessed on August 19, 2015.

[5] Joseph J. Bozell, Gene R. Petersen: Technology development for the production of biobased products from biorefinery carbohydrates — the US Department of Energy's “Top 10” revisited . In: Green Chemistry . tape 12 , no. January 4 , 2010, doi : 10.1039 / b922014c .

[6] Segetis Technology ( Memento of the original from September 12, 2015 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2