625-33-2
Chemical Structure
3-Penten-2-one
Synonym(s): Ethylideneacetone; (3Z)-pent-3-en-2-one
- CAS No.: 625-33-2
- Formula:C5H8O
- Molecular Weight:84.12
IUPAC Name: (E)-pent-3-en-2-one
InChIKey: LABTWGUMFABVFG-ONEGZZNKSA-N
SMILES: CC(/C=C/C)=O
Biological Activity: 3‑Penten‑2‑one (Ethylideneacetone; (3Z)-pent-3-en-2-one) is an endogenous metabolite and a small-molecule ketone with antifungal activity. 3‑Penten‑2‑one induces HO‑1 expression, inhibits iNOS expression and NO production in lipopolysaccharide-activated RAW264.7 macrophages, and exerts anti-inflammatory effects. 3‑Penten‑2‑one inhibits the growth of Penicillium italicum, disrupts fungal hyphal and spore morphology and damages the cell membrane, and also exhibits inhibitory activity against various plant pathogenic fungi. 3-Penten-2-one can be used in research related to fungal infections and inflammatory diseases[1][2][3][4][5].
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3-Penten-2-one | 98.29% | 3‑Penten‑2‑one (Ethylideneacetone; (3Z)-pent-3-en-2-one) is an endogenous metabolite and a small-molecule ketone with antifungal activity. 3‑Penten‑2‑one induces HO‑1 expression, inhibits iNOS expression and NO production in lipopolysaccharide-activated RAW264.7 macrophages, and exerts anti-inflammatory effects. 3‑Penten‑2‑one inhibits the growth of Penicillium italicum, disrupts fungal hyphal and spore morphology and damages the cell membrane, and also exhibits inhibitory activity against various plant pathogenic fungi. 3-Penten-2-one can be used in research related to fungal infections and inflammatory diseases. | ||||||||||||||||||||
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References
- [1]. Kil JS, et al. Okanin, a chalcone found in the genus Bidens, and 3-penten-2-one inhibit inducible nitric oxide synthase expression via heme oxygenase-1 induction in RAW264.7 macrophages activated with lipopolysaccharide. Journal of clinical biochemistry and nutrition. 2012 Jan;50(1):53-8.
- [2]. Gueldner RC, et al. Volatile compounds inhibiting Aspergillus flavus. Journal of Agricultural and Food Chemistry. 1985 May;33(3):411-3.
- [3]. Temple Jr C, et al. Synthesis of potential antimalarial agents. Preparation of some 6-amino-5, 8-dimethoxyquinolines and the corresponding 6-amino-5, 8-quinolinediones. Journal of Medicinal Chemistry. 1974 Jun;17(6):615-9.
- [4]. Ling L, et al. Antifungal activity and application of Neurospora sitophila Y-4 against postharvest Penicillium italicum of Citrus reticulata'Shiyue Ju'via 3-penten-2-one. Food Bioscience. 2025 Oct 3:107706.
- [5]. Stulanovic N, et al. Antifungal and other bioactive properties of the volatilome of Streptomyces scabiei. Applied and Environmental Microbiology. 2025;91(10).