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L2009

Sigma-Aldrich

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
Beilstein:
506796
EC Number:
204-649-2
MDL number:
MFCD00002796
UNSPSC Code:
12352100
PubChem Substance ID:
24896298
NACRES:
NA.22

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.)

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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H317,H318

Hazard Classifications

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

208.4 °F - closed cup

Flash Point(C)

98 °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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Synthesis of a New Type Perfume Fraistone [J].
Heping L, et al.
Fine Chemicals / ????, 6 (1998)
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)
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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