What is Tetronic acid?
Feb 19，2020
Tetronic acid is a crystalline enolic lactone C4H4O3 that has acidic properties and is the parent compound of acidic compounds obtained by the fermenting action of a mold (Penicillium charlesii) from spoiled corn.
Fig 1. Chemical structure formula and three-dimensional structure of TETRONIC ACID
Tetronic acid is used as a precursor of a variety of substituted and ring-fused furans and butenolides. It is an acidic building block for heterocyclic compounds for medicinal applications. It is used for selective O-alkyaltion reactions involving cesium fluoride. It is also used to prepare 3H-furo[3,4-b]quinolin-1-one by reacting with 2-amino-benzaldehyde.
It interconverts between keto and enol tautomers:
Many natural products such as ascorbic acid (vitamin C), penicillic acid, pulvinic acids, and abyssomicins possess the β-keto-γ-butyrolactone motif of tetronic acid.
In organic synthesis, it is used as a precursor for other substituted and ring-fused furans and butenolides. It is also forms the structural core of a class of pesticides, known as tetronic acid insecticides, which includes spirodiclofen and spiromesifen[1-3].
Tetronic acid belong to the class of 4-hydroxybutenolides that are characterized by a 4-hydroxy-2(5H)-furanone ring, as it can be seen in the generic structure. This type of five-membered vinylogous acids can be met in two main tautomeric forms with enol structure 1 being the one that predominates. Tetronic acid is a substructural element of many natural products of various classes such as alkaloids, terpenes, macrolides, and tannins. Two well-known natural products of this class are ascorbic acid and penicillic acid. In many cases, its presence in natural products is connected with a wide range of significant biological properties and, therefore, the synthesis of these compounds has attracted synthetic interest for more than a century. In the following section, a synopsis of the natural occurrence, biological activities, and biosynthetic considerations of tetronic acid natural products will be attempted and a more thorough analysis of the synthetic strategies toward such compounds will be presented. Categorization of tetronic structures is based on 5-position’s substitution and discussion on synthetic routes toward these compounds will be limited on total syntheses with main focus to the construction of tetronic ring.
Tetramic acid derivatives constitute an important class of nitrogen heterocycles with pyrrolidine-2,4-dione moieties and are key structural motifs in many natural products of terrestrial and marine origin.They exhibit a wide range of biological activities including antibiotic, antiviral, antifungal, cytotoxic and enzyme inhibitory activities against bacterial DNA-directed RNA polymerases[4,5].
References
[1]Abdou, Moaz M.; El-Saeed, Rasha A.; Abozeid, Mohamed A.; Elattar, Khaled M.; Zaki, E.G.; Barakat, Y.; Ibrahim, V.; Fathy, Mahmoud; Amine, M.; Bondock, Samir (2015). "Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions". Arabian Journal of Chemistry.
[2]Georgiadis, Dimitris; Zografos, Alexandros (2006). "Synthetic Strategies towards Naturally Occurring Tetronic Acids". Synthesis. 2006 (19): 3157.
[3]Schmidt, Diane Grob; Seemuth, Paul D.; Zimmer, Hans (1983). "Substituted .gamma.-butyrolactones. Part 31. 2,4(3H,5H)-Furandione: Heteroannulations with aromatic o-amino carbonyl compounds and condensations with some vic-polyones". The Journal of Organic Chemistry. 48 (11): 1914.
[4]Reusser, F. Tirandamycin, an Inhibitor of Bacterial Ribonucleic Acid Polymerase[J]. Antimicrobial Agents & Chemotherapy, 10(4):618-622.
[5]Lang G, Cole A L, Blunt J W, et al. An unusual oxalylated tetramic acid from the New Zealand basidiomycete Chamonixia pachydermis[J]. 2006, 69(1):151-3.
Lastest Price from TETRONIC ACID manufacturers
TETRONIC ACID
US $0.00-0.00/KG2024-11-05
- CAS:
- 4971-56-6
- Min. Order:
- 1KG
- Purity:
- 99%
- Supply Ability:
- 500000kg
TETRONIC ACID
US $1.00-100.00/KG2024-08-17
- CAS:
- 4971-56-6
- Min. Order:
- 1KG
- Purity:
- 95%
- Supply Ability:
- 300KG