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Levulinic acid

analytical standard

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Synonym(s):
4-Oxopentanoic acid, 4-Oxovaleric acid
Linear Formula:
CH3COCH2CH2COOH
CAS Number:
123-76-2
Molecular Weight:
116.12
Beilstein:
506796
EC Number:
204-649-2
MDL number:
MFCD00002796
UNSPSC Code:
85151701
PubChem Substance ID:
329756110
NACRES:
NA.24

grade

analytical standard

Quality Level

100

vapor pressure

1 mmHg ( 102 °C)

Assay

≥97.5% (GC)
97.5-102.5% (T)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

bp

245-246 °C (lit.)

mp

30-33 °C (lit.)

density

1.134 g/mL at 25 °C (lit.)

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

format

neat

SMILES string

CC(=O)CCC(O)=O

InChI

1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)

InChI key

JOOXCMJARBKPKM-UHFFFAOYSA-N

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General description

Levulinic acid (LA), is a biogenic product of hexose acid hydrolysis, produced from renewable or bio-based resources. LA is reported to react with a variety of compounds to result in products, which are widely used in pharmaceuticals, personal care products, electronics, plasticizers, antifouling compounds, fuels, solvents, polymers, anti-freeze agents, batteries, coatings, biologically active materials, corrosion inhibitors, adsorbents, etc. LA is also employed as a chemical intermediate in the production of biodegradable polymers, fuel extenders, herbicides, flavors, antibiotics and useful 5-carbon compounds.
This substance is listed on the positive list of the EU regulation 10/2011 for plastics intended to come into contact with food. Find all available reference materials for compounds listed in 10/2011 here

Application

Levulinic acid may be used as an analytical reference standard
for the quantification of the analyte in the following:
  • Soy sauce using liquid chromatography coupled to mass spectrometry (LC–MS).
  • Liquid food samples using gas chromatography with flame ionization detection (GC-FID).

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H317,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1

WGK

WGK 2

Flash Point(F)

208.4 °F

Flash Point(C)

98 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Review on the conversion of levulinic acid and its esters to various useful chemicals
Adeleye TA, et al.
AIChE Journal, 7(2), 165-165 (2019)
Levulinic acid
Hachula B, et al.
Acta Crystallographica Section E, Structure Reports Online, 69(9) (2013)
Determination of levulinic acid in soy sauce by liquid chromatography with mass spectrometric detection
Sano A, et al.
Food Chemistry, 105(3), 1242-1247 (2007)
A rapid gas chromatographic method for direct determination of short-chain (C2?C12. volatile organic acids in foods
Yang H-M and Choong M-Y
Food Chemistry, 75(1), 101-108 (2001)
F Monlau et al.
Bioresource technology, 187, 379-386 (2015-04-13)
The robust supramolecular structure of biomass often requires severe pretreatments conditions to produce soluble sugars. Nonetheless, these processes generate some inhibitory compounds (i.e. furans compounds and aliphatic acids) deriving mainly from sugars degradation. To avoid the inhibition of the biological
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