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Merck

L2009

Levulinic acid

98%

Synonym(s):

4-Oxopentanoic acid, 4-Oxovaleric acid

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About This Item

Linear Formula:
CH3COCH2CH2COOH
CAS Number:
123-76-2
Molecular Weight:
116.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24896298
EC Number:
204-649-2
Beilstein/REAXYS Number:
506796
MDL number:
MFCD00002796

Product Name

Levulinic acid, 98%

InChI key

JOOXCMJARBKPKM-UHFFFAOYSA-N

InChI

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

SMILES string

CC(=O)CCC(O)=O

vapor pressure

1 mmHg ( 102 °C)

assay

98%

bp

245-246 °C (lit.)

mp

30-33 °C (lit.)

density

1.134 g/mL at 25 °C (lit.)

Quality Level

200

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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
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

13 - Non Combustible Solids

wgk

WGK 2

flash_point_f

208.4 °F - closed cup

flash_point_c

98 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB3157
STBL4370
STBL1993
STBK6939
STBK6193

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Synthesis of a New Type Perfume Fraistone [J].
Heping L, et al.
Fine Chemicals / ????, 6 (1998)
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
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)
Selective and Efficient Iridium Catalyst for the Reductive Amination of Levulinic Acid into Pyrrolidones.
Wang S, et al.
ChemSusChem, 10(21), 4150-4154 (2017)
Diego Garcés et al.
ChemSusChem, 12(4), 924-934 (2018-12-15)
Homogeneous (HCl) and heterogeneous catalysts (various zeolites) were combined to enhance the upgrading of glucose into two different platform molecules: 5-hydroxymethylfurfural (HMF) and levulinic acid (LA). β-Zeolite was the most active material for the glucose isomerization to fructose, improving also
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