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L2009

Sigma-Aldrich

Levulinic acid

98%

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Synonym(s):
4-Oxopentanoic acid, 4-Oxovaleric acid
Linear Formula:
CH3COCH2CH2COOH
CAS Number:
Molecular Weight:
116.12
Beilstein:
506796
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

1 mmHg ( 102 °C)

Quality Level

Assay

98%

bp

245-246 °C (lit.)

mp

30-33 °C (lit.)

density

1.134 g/mL at 25 °C (lit.)

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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Application

Levulinic acid is a precursor for the synthesis of useful intermediates such as γ-valerolactone, ethyl levulinate, pentanoic acid and 2-methyl-tetrahydrofuran. Derivatization and esterification of levulinic acid results in potential biofuels.

It can also be used in:
  • The preparation of catalytic composite to synthesize 5-hydroxymethylfurfural and furfural.
  • The synthesis of a commercial fragrance, fraistone.
  • The synthesis of pyrrolidone derivatives via reductive amination.
  • The total synthesis of mycobacterial arabinogalactan.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Environmentally benign catalytic process for esterification of renewable levulinic acid to various alkyl levulinates biodiesel.
Nandiwale KY and Bokade VV
Environmental Progress & Sustainable Energy, 34(3), 795-801 (2015)
Vapor Phase Catalytic Transfer Hydrogenation (CTH) of Levulinic Acid to ?-Valerolactone Over Copper Supported Catalysts Using Formic Acid as Hydrogen Source.
Lomate S, et al.
Catalysis Letters, 148(1), 348-358 (2018)
Catalytic transformation of lignocellulose into chemicals and fuel products in ionic liquids.
Zhang Z, et al.
Chemical Reviews, 117(10), 6834-6880 (2016)
Nam H Phan et al.
Anti-cancer agents in medicinal chemistry, 18(9), 1349-1355 (2017-11-28)
The aim of this study was to develop and compare polymeric micelles of fucoidan, a sulfated polysaccharide, and hydrophobic drugs such as paclitaxel and curcumin. Paclitaxel and curcumin are both known for their medicinal properties, including anticancer efficacy. However, their
Synthesis of a New Type Perfume Fraistone [J].
Heping L, et al.
Fine Chemicals / ????, 6 (1998)

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