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283754

Sigma-Aldrich

2(5H)-Furanone

98%

Synonym(s):

γ-Crotonolactone, 2-Buten-1,4-olide

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About This Item

Empirical Formula (Hill Notation):
C4H4O2
CAS Number:
497-23-4
Molecular Weight:
84.07
Beilstein/REAXYS Number:
383585
EC Number:
207-839-3
MDL number:
MFCD00005376
UNSPSC Code:
12352100
PubChem Substance ID:
24857130
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.469 (lit.)

bp

86-87 °C/12 mmHg (lit.)

mp

4-5 °C (lit.)

density

1.185 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

O=C1OCC=C1

InChI

1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

InChI key

VIHAEDVKXSOUAT-UHFFFAOYSA-N

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General description

Chiral urea compounds catalyzed hetero-Michael addition reaction of 2(5H)-furanone (γ-crotonolactone) to pyrrolidine. The quorum sensing inhibition activity by 2(5H)-furanone was studied using bioindicator strains.

Application

2(5H)-Furanone (γ-Crotonolactone) has been used in:
  • synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid
  • synthesis of 5-substituted 2(5H) furanones (γ-butenolides) via direct aldol reaction with aromatic aldehydes catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts
  • Michael addition reactions for synthesis of lignans
  • three-component Michael-Aldol reactions with an aldehyde anda thiolate or carbanion

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

213.8 °F - closed cup

flash_point_c

101 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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Tetrahedron, 49, 9039-9039 (1993)
Tetrahedron, 49, 8073-8073 (1993)
Tetrahedron, 49, 4173-4173 (1993)
Yoshihiro Sohtome et al.
Chemical & pharmaceutical bulletin, 52(4), 477-480 (2004-04-02)
Chiral urea compounds 10a-g were synthesized as catalysts for conjugate addition of pyrrolidine (2) to gamma-crotonolactone (3). In the presence of a catalytic amount of the chiral ureas, this hetero-Michael reaction was greatly accelerated. Asymmetric induction was observed with the
Rebecca J Chesterfield et al.
ACS synthetic biology, 9(8), 2107-2118 (2020-08-14)
Strigolactones are plant hormones and rhizosphere signaling molecules with key roles in plant development, mycorrhizal fungal symbioses, and plant parasitism. Currently, sensitive, specific, and high-throughput methods of detecting strigolactones are limited. Here, we developed genetically encoded fluorescent strigolactone biosensors based
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