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61405

Sigma-Aldrich

Methyl levulinate

greener alternative

≥98.0%

Synonym(s):

4-Oxopentanoic acid methyl ester, 4-Oxovaleric acid methyl ester, Methyl β-acetylpropionate, Methyl 4-oxopentanoate, Methyl 4-oxovalerate, Methyl levulate

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About This Item

Linear Formula:
CH3COCH2CH2COOCH3
CAS Number:
624-45-3
Molecular Weight:
130.14
Beilstein:
1754008
EC Number:
210-846-4
MDL number:
MFCD00017499
UNSPSC Code:
12352100
PubChem Substance ID:
57651849
NACRES:
NA.22

Assay

≥98.0%

greener alternative product characteristics

Safer Solvents and Auxiliaries
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

refractive index

n20/D 1.422

bp

193-195 °C (lit.)

density

1.051 g/mL at 20 °C (lit.)

greener alternative category

Aligned,

SMILES string

COC(=O)CCC(C)=O

InChI

1S/C6H10O3/c1-5(7)3-4-6(8)9-2/h3-4H2,1-2H3

InChI key

UAGJVSRUFNSIHR-UHFFFAOYSA-N

Related Categories

General description

Methyl levulinate can be synthesized from glucose in the presence of a few drops of dilute sulfuric acid in methanol.
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Application

Methyl levulinate can undergo Meerwein–Ponndorf–Verley (MPV) reduction in the presence of lewis acid zeolite like Hf-beta to give 4-hydroxypentanoates.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

161.6 °F - closed cup

Flash Point(C)

72 °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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Lutz F Tietze et al.
Organic letters, 14(16), 4035-4037 (2012-08-03)
An efficient total synthesis of (+)-(R)-Pinnatolide is described. As a key step an asymmetric multicomponent domino allylation reaction of methyl levulinate is used to form the quaternary stereogenic center in a highly selective way.
"Investigation of the reaction kinetics of isolated Lewis acid sites in beta zeolites for the Meerwein?Ponndorf?Verley reduction of methyl levulinate to ?-valerolactone"
<BIG>Luo.YH, et al.</BIG>
J. Catal., 320, 198-207 (2014)
Methyl-ALA-induced fluorescence in photodynamic diagnosis of basal cell carcinoma prior to Mohs micrographic surgery.
Pedro Redondo et al.
Archives of dermatology, 144(1), 115-117 (2008-01-23)
Xiaoyu Wu et al.
Carbohydrate research, 358, 37-39 (2012-07-31)
One-pot preparation of methyl levulinate (MLA) from cellulose in near-critical methanol was studied. Acids containing SO(3)H group were proven to be effective catalysts for the production of MLA from cellulose's catalytic alcoholysis. The effects of different reaction conditions, such as
F J Eller
Journal of AOAC International, 82(3), 766-769 (1999-07-17)
Gas chromatographic fatty acid methyl ester (GC-FAME) analyses of some acid-hydrolyzed foods revealed a large peak that did not correspond to any FAME standards. The unknown peak eluted just after the C12 FAME. If the fatty acid response factor and
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