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393509

Sigma-Aldrich

3-Methyl-2(5H)-furanone

technical grade, 90%

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

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About This Item

Empirical Formula (Hill Notation):
C5H6O2
CAS Number:
22122-36-7
Molecular Weight:
98.10
Beilstein/REAXYS Number:
1642
MDL number:
MFCD00191545
UNSPSC Code:
12352100
PubChem Substance ID:
24864521
NACRES:
NA.22

grade

technical grade

Quality Level

100

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

200.1 °F - closed cup

flash_point_c

93.4 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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)
A Useful Synthesis of 3-Methyl-2 (5H)-Furanone.
Cruz-Almanza R and Padilla Higareda F.
Synthetic Communications, 21(8-9), 1097-1104 (1991)
The Influence of Microwave Drying on Biomass Pyrolysis.
Wang X, et al.
Energy and Fuels, 22(1), 67-74 (2007)
Mengcen Wang et al.
PloS one, 8(11), e78024-e78024 (2013-11-14)
The tropolone-tolerant Trichoderma virens PS1-7 is a biocontrol agent against Burkholderia plantarii, causative of rice seedling blight. When exposed to catechol, this fungus dose-dependently produced carot-4-en-9,10-diol, a sesquiterpene-type autoregulatory signal molecule that promotes self-conidiation of T. virens PS1-7 mycelia. It
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