L2009
Levulinic acid
98%
Synonym(s):
4-Oxopentanoic acid, 4-Oxovaleric acid
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About This Item
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)
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:
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.
Signal Word
Danger
Hazard Statements
Precautionary 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
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Total synthesis of mycobacterial arabinogalactan containing 92 monosaccharide units.
Wu Y, et al.
Nature Communications, 8, 14851-14851 (2017)
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)
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)
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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