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Merck

61405

Sigma-Aldrich

Methyl levulinate

greener alternative

≥98.0%

Sinónimos:

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

Fórmula lineal:
CH3COCH2CH2COOCH3
Número de CAS:
Peso molecular:
130.14
Beilstein/REAXYS Number:
1754008
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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.)

functional group

ester
ketone

greener alternative category

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

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

161.6 °F - closed cup

flash_point_c

72 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Visite la Librería de documentos

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)
Failure to treat keratoderma in Papillon-Lefevre syndrome using photodynamic therapy.
Montse Fernández-Guarino et al.
European journal of dermatology : EJD, 17(5), 456-457 (2007-08-04)
"Extremely low sulfuric acid catalyst system for synthesis of methyl levulinate from glucose"
<BIG>Peng L, et al.</BIG>
Industrial Crops and Products, 40, 136-144 (2012)

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