All Photos(2)
Synonym(s):
4-Oxopentanoic acid methyl ester, 4-Oxovaleric acid methyl ester, Methyl β-acetylpropionate, Methyl 4-oxopentanoate, Methyl 4-oxovalerate, Methyl levulate
Linear Formula:
CH3COCH2CH2COOCH3
CAS Number:
Molecular Weight:
130.14
Beilstein:
1754008
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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.
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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.
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
"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)
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)
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