28005
γ-Crotonolactone
purum, ≥97.5% (GC)
Synonym(s):
2-Buten-1,4-olide
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About This Item
Empirical Formula (Hill Notation):
C4H4O2
CAS Number:
Molecular Weight:
84.07
EC Number:
207-839-3
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
383585
MDL number:
grade
purum
assay
≥97.5% (GC)
refractive index
n20/D 1.469 (lit.), n20/D 1.471
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
Application
γ-Crotonolactone has been used in the synthesis of:
- (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid
- diastereomerically and enantiomerically enriched 5-substituted 2(5H) furanones (γ-butenolides) via direct aldol reaction with various aromatic aldehydes catalyzed by organocatalysts
Other Notes
Review
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
Regulatory Information
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Y.S. Rao
Chemical Reviews, 76, 625-625 (1976)
Weihong Wang et al.
Journal of natural products, 75(12), 2049-2054 (2012-11-14)
Six new (1, 2, and 5-8) and three known (3, 4, and 9) butenolide metabolites were isolated from the tunicate Pseudodistoma antinboja by activity-guided fractionations. The structures were elucidated by combined NMR and MS spectroscopic methods. These compounds were evaluated
Mark T Waters et al.
Development (Cambridge, England), 139(7), 1285-1295 (2012-02-24)
Karrikins are butenolides derived from burnt vegetation that stimulate seed germination and enhance seedling responses to light. Strigolactones are endogenous butenolide hormones that regulate shoot and root architecture, and stimulate the branching of arbuscular mycorrhizal fungi. Thus, karrikins and strigolactones
Ramona Riclea et al.
Chembiochem : a European journal of chemical biology, 13(11), 1635-1644 (2012-07-04)
The volatiles released by several streptomycetes were collected by using a closed-loop stripping apparatus (CLSA) and analysed by GC-MS. The obtained headspace extracts of various species contained blastmycinone, a known degradation product of the fungicidal antibiotic, antimycin A(3b), and several
Sunil V Pansare et al.
Organic & biomolecular chemistry, 10(10), 2119-2125 (2012-02-02)
The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.
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