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L2009

Sigma-Aldrich

Levulinic acid

98%

Synonym(s):
4-Oxopentanoic acid, 4-Oxovaleric acid
Linear Formula:
CH3COCH2CH2COOH
CAS Number:
Molecular Weight:
116.12
Beilstein:
506796
EC Number:
MDL number:
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.

Packaging

50, 250 g in poly bottle
1 kg in poly bottle

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Total synthesis of mycobacterial arabinogalactan containing 92 monosaccharide units.
Wu Y, et al.
Nature Communications, 8, 14851-14851 (2017)
Hydrodeoxygenation activity of W modified Ni/H-ZSM-5 catalyst for single step conversion of levulinic acid to pentanoic acid: An insight on the reaction mechanism and structure activity relationship.
Velisoju VK, et al.
Applied Catalysis, 550, 142-150 (2018)
Levulinic Acid as a Catalyst for the Production of 5?Hydroxymethylfurfural and Furfural from Lignocellulose Biomass.
Seemala B, et al.
ChemCatChem, 8(3), 640-647 (2016)
Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels.
Climent MJ, et al.
Green Chemistry, 16(2), 516-547 (2014)
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

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