283754
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:
Molecular Weight:
84.07
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-839-3
Beilstein/REAXYS Number:
383585
MDL number:
Assay:
98%
Form:
liquid
Product Name
2(5H)-Furanone, 98%
InChI key
VIHAEDVKXSOUAT-UHFFFAOYSA-N
InChI
1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
SMILES string
O=C1OCC=C1
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.)
functional group
ester
storage temp.
2-8°C
Quality Level
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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
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.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
10 - Combustible liquids
wgk
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
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Filip Sima et al.
Frontiers in microbiology, 9, 2139-2139 (2018-09-25)
Human campylobacteriosis is considered one of the most common foodborne diseases worldwide with poultry identified as the main source of infection accounting for 50-80% of human cases. Highly virulent Campylobacter spp., positive for the Type VI secretion system (T6SS), which
Tetrahedron, 49, 4173-4173 (1993)
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
Pedro Rodríguez-López et al.
Foods (Basel, Switzerland), 8(12) (2019-12-11)
Furanones are analogues of acylated homoserine lactones with proven antifouling activity in both Gram-positive and Gram-negative bacteria though the interference of various quorum sensing pathways. In an attempt to find new strategies to prevent and control Listeria monocytogenes biofilm formation
Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions.
Wen Zhang et al.
Angewandte Chemie (International ed. in English), 51(40), 10069-10073 (2012-09-07)
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