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Safety Information

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

L2009-250G:
L2009-VAR:
L2009-50G:
L2009-25KG:
L2009-1KG:
L2009-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6939
STBK6193
STBK3811
STBK2663
STBK0029

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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
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)
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
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