Levulinic acid (Laevulinic acid; Levulic acid; NSC 3716) is a precursor for the synthesis of biofuels, such as ethyl levulinate. Levulinic acid is also used as a precursor for pharmaceuticals, plasticizers, and various other additives. The largest application of levulinic acid is its use in the production of aminolevulinic acid, a biodegradable herbicide used in South Asia. Another key application is the use of levulinic acid in cosmetics. Ethyl levulinate, a primary derivative of levulinic acid, is extensively used in fragrances and perfumes. Levulinic acid is a chemical building block or starting material for a wide variety of other compounds including γ-valerolactone and 2-methyl-THF. Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH3C(O)CH2CH2CO2H. It is classified as a keto acid. This white crystalline solid is soluble in water and polar organic solvents. It is derived from degradation of cellulose and is a potential precursor to biofuels, such as ethyl levulinate.

Physicochemical Properties

Molecular Formula	C5H8O3
Molecular Weight	116.11522
Exact Mass	116.047
CAS #	123-76-2
Related CAS #	Levulinic acid-d5;1206185-52-5
PubChem CID	11579
Appearance	Colorless to off-white <30°C powder,>33°C liquid
Density	1.1±0.1 g/cm3
Boiling Point	242.9±13.0 °C at 760 mmHg
Melting Point	30-33 °C(lit.)
Flash Point	137.8±0.0 °C
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.435
LogP	-0.49
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Heavy Atom Count	8
Complexity	106
Defined Atom Stereocenter Count	0
SMILES	CC(CCC(O)=O)=O
InChi Key	JOOXCMJARBKPKM-UHFFFAOYSA-N
InChi Code	InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
Chemical Name	4-oxopentanoic acid
Synonyms	4-Oxovaleric acid; Laevulinic acid; Levulic acid; NSC 3716; NSC3716; NSC-3716; β-Acetylpropionic acid; γ-Ketovaleric acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1]. Levulinic Acid Biorefineries: New Challenges for Efficient Utilization of Biomass. ChemSusChem. 2016 Mar 21;9(6):562-82.

Additional Infomation

4-oxopentanoic acid is an oxopentanoic acid with the oxo group in the 4-position. It has a role as a plant metabolite. It is a straight-chain saturated fatty acid and an oxopentanoic acid. It is a conjugate acid of a 4-oxopentanoate. Levulinic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Levulinic acid has been reported in Dendronephthya hemprichi with data available. See also: ... View More ...

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~861.18 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (21.53 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (21.53 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (21.53 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	8.6118 mL	43.0589 mL	86.1178 mL
	5 mM	1.7224 mL	8.6118 mL	17.2236 mL
	10 mM	0.8612 mL	4.3059 mL	8.6118 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.