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Sigma-Aldrich

3-Methyl-2(5H)-furanone

technical grade, 90%

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Synonym(s):
α-Methyl-γ-crotonolactone, 2-Methyl-2-butenolide, 2-Methylbut-2-en-4-olide, 3-Methyl-2,5-dihydrofuran-2-one, 3-Methyl-5H-furan-2-one, 4-Hydroxy-2-methyl-2-butenoic acid γ-lactone
Empirical Formula (Hill Notation):
C5H6O2
CAS Number:
Molecular Weight:
98.10
Beilstein/REAXYS Number:
1642
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

assay

90%

form

liquid

refractive index

n20/D 1.467 (lit.)

bp

97-99 °C/20 mmHg (lit.)

density

1.13 g/mL at 25 °C (lit.)

SMILES string

CC1=CCOC1=O

InChI

1S/C5H6O2/c1-4-2-3-7-5(4)6/h2H,3H2,1H3

InChI key

VGHBEMPMIVEGJP-UHFFFAOYSA-N

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General description

3-Methyl-2(5H)-furanone (3-Methylfuran-2(5H)-one) has been synthesized in highest yield (77%) by employing α-methyl-γ- butyrolactone as starting reagent.
3-Methyl-2(5H)-furanone, a five membered conjugated lactone, is a volatile compound. Its synthesis has been reported. It is reported to be one of the predominant constituent of the flavor of pandan leaves. It is also found in Thai soy sauce, Arabica roasted coffee samples from Brazil, bio-oil from pine wood sawdust.

Application

3-Methyl-2(5H)-furanone is the suitable model compound used to investigate the fragmentation mechanism of five membered lactones by electrospray ionisation tandem mass spectrometry and also to study the airway irritation of isoprene, isoprene/ozone, and isoprene/ozone/nitrogen dioxide mixture.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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A New Expedient Synthesis of 3-Methyl-2 (5H)-furanone, the Common Substructure in Strigolactones, and Its Proposed Biosynthesis.
Malik H, et al.
Synthesis, 19, 3271-3273 (2010)
The fragmentation mechanism of five-membered lactones by electrospray ionisation tandem mass spectrometry.
Crotti AEM, et al.
International Journal of Mass Spectrometry, 232(3), 271-276 (2004)
A Useful Synthesis of 3-Methyl-2 (5H)-Furanone.
Cruz-Almanza R and Padilla Higareda F.
Synthetic Communications, 21(8-9), 1097-1104 (1991)
An efficient and short synthesis of 3-methyl-2 (5H)-furanone, a synthon for strigol analogues.
Mangnus EM and Zwanenburg B
Synthetic Communications, 22(5), 783-786 (1992)
Supercritical carbon dioxide extraction of 2-acetyl-1-pyrroline and volatile components from pandan leaves.
Laohakunjit N and Noomhorm A.
Flavour and Fragrance Journal, 19(3), 251-259 (2004)

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