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547-65-9 | alpha-Methylene-gamma-butyrolactone
CAS No: 547-65-9 Catalog No: AG003NSD MDL No:MFCD00005407
Product Description
Catalog Number:
AG003NSD
Chemical Name:
alpha-Methylene-gamma-butyrolactone
CAS Number:
547-65-9
Molecular Formula:
C5H6O2
Molecular Weight:
98.0999
MDL Number:
MFCD00005407
IUPAC Name:
3-methylideneoxolan-2-one
InChI:
InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
InChI Key:
GSLDEZOOOSBFGP-UHFFFAOYSA-N
SMILES:
C=C1CCOC1=O
EC Number:
208-931-6
UNII:
362Y256BOL
NSC Number:
205367
Properties
Complexity:
115
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
98.037g/mol
Formal Charge:
0
Heavy Atom Count:
7
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
98.101g/mol
Monoisotopic Mass:
98.037g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
26.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.8
Literature
| Title | Journal |
|---|---|
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| Zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis method for α-methylene-γ-butyrolactone. | Organic & biomolecular chemistry 20120528 |
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| Purification and characterization of a tuliposide-converting enzyme from bulbs of Tulipa gesneriana. | Bioscience, biotechnology, and biochemistry 20090801 |
| Dimethoxycurcumin, a Synthetic Curcumin Analogue, Induces Heme Oxygenase-1 Expression through Nrf2 Activation in RAW264.7 Macrophages. | Journal of clinical biochemistry and nutrition 20090101 |
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| Induction of G2-M phase arrest and apoptosis by alpha-methylene-gamma-butyrolactones in human leukemia cells. | Cancer letters 20080928 |
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| Costunolide inhibits production of tumor necrosis factor-alpha and interleukin-6 by inducing heme oxygenase-1 in RAW264.7 macrophages. | Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20071201 |
| The alpha-methylene-gamma-butyrolactone moiety in dehydrocostus lactone is responsible for cytoprotective heme oxygenase-1 expression through activation of the nuclear factor E2-related factor 2 in HepG2 cells. | European journal of pharmacology 20070622 |
| Cross-metathesis between alpha-methylene-gamma-butyrolactone and olefins: a dramatic additive effect. | Organic letters 20070426 |
| Cross metathesis of alpha-methylene lactones II: gamma- and delta-lactones. | Organic letters 20070426 |
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| Synthesis and anti-viral activity of a series of sesquiterpene lactones and analogues in the subgenomic HCV replicon system. | Bioorganic & medicinal chemistry 20060101 |
| Home gardening may be a risk factor for contact dermatitis to Alstroemeria. | Allergologia et immunopathologia 20060101 |
| Synthesis of a laterally branched polyamine from alpha-methylene-gamma-butyrolactone. | Organic letters 20050623 |
| C75 [4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid] activates carnitine palmitoyltransferase-1 in isolated mitochondria and intact cells without displacement of bound malonyl CoA. | The Journal of pharmacology and experimental therapeutics 20050101 |
| Targeting fatty acid synthase: potential for therapeutic intervention in her-2/neu-overexpressing breast cancer. | Drug news & perspectives 20050101 |
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| Inhibition of ICAM-1 gene expression, monocyte adhesion and cancer cell invasion by targeting IKK complex: molecular and functional study of novel alpha-methylene-gamma-butyrolactone derivatives. | Carcinogenesis 20041001 |
| Isolation of an alpha-methylene-gamma-butyrolactone derivative, a toxin from the plant pathogen Lasiodiplodia theobromae. | Phytochemistry 20041001 |
| Inactivation of the cytotoxic activity of repin, a sesquiterpene lactone from Centaurea repens. | Chemical research in toxicology 20040901 |
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| Three-dimensional pharmacophore mapping of certain anticancer alpha-methylene-gamma-butyrolactones. | Oncology research 20030101 |
| Highly enantioselective syntheses of functionalized alpha-methylene-gamma-butyrolactones via Rh(I)-catalyzed intramolecular Alder ene reaction: application to formal synthesis of (+)-pilocarpine. | Journal of the American Chemical Society 20020717 |
| Synthesis and antiproliferative activity of a new compound containing an alpha-methylene-gamma-lactone group. | Journal of medicinal chemistry 20020606 |
| Synthesis and cytotoxic evaluation of alpha-methylene-gamma-butyrolactone bearing naphthalene and naphtho[2,1-b]furan derivatives. | European journal of medicinal chemistry 20020401 |
| Inhibitory mechanism of costunolide, a sesquiterpene lactone isolated from Laurus nobilis, on blood-ethanol elevation in rats: involvement of inhibition of gastric emptying and increase in gastric juice secretion. | Alcohol and alcoholism (Oxford, Oxfordshire) 20020101 |
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| Fingertip dermatitis in a retail florist. | Cutis 20010401 |
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| Allergic contact dermatitis to laurel (Laurus nobilis L.): isolation and identification of haptens. | Archives of dermatological research 19840101 |
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