Canadensolide
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| Category | Others |
| Catalog number | BBF-00207 |
| CAS | 20421-31-2 |
| Molecular Weight | 210.23 |
| Molecular Formula | C11H14O4 |
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Description
Canadensolide is a bislactone antibiotic isolated from Penicillium canadense, Aspergillus flavus and A. tamarii. It shows antifungal activity.
Specification
| Synonyms | (-)-Canadensolide; Furo(3,4-b)furan-2,4-dione, 6-butyltetrahydro-3-methylene-, (3aS,6R,6aR)-; (3aS,6R,6aR)-6-Butyl-3-methylenetetrahydrofuro[3,4-b]furan-2,4-dione |
| IUPAC Name | (3aS,6R,6aR)-6-butyl-3-methylidene-6,6a-dihydro-3aH-furo[3,4-b]furan-2,4-dione |
| Canonical SMILES | CCCCC1C2C(C(=C)C(=O)O2)C(=O)O1 |
| InChI | InChI=1S/C11H14O4/c1-3-4-5-7-9-8(11(13)14-7)6(2)10(12)15-9/h7-9H,2-5H2,1H3/t7-,8+,9+/m1/s1 |
| InChI Key | IYSGHKQBSLXKPO-VGMNWLOBSA-N |
Properties
| Boiling Point | 426.2±45.0°C at 760 mmHg |
| Melting Point | 46-47.5°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Identification of bioactive metabolites dihydrocanadensolide, Kojic acid, and vanillic acid in soy sauce using GC-MS, NMR spectroscopy, and single-crystal X-ray diffraction
Qin Wang, Kirk L Parkin, Qingli Zhang, Ying Li, Wei Luo, Deyun Ma, Zi Teng, Mouming Zhao J Agric Food Chem . 2014 Aug 20;62(33):8392-401. doi: 10.1021/jf502159m.
Microbial transformations of intrinsic substrates offer immense potential for generating new bioactive compounds in fermented food products. The aim of this work was to characterize the secondary metabolites in soy sauce, one of the oldest fermented condiments. Ethyl acetate extract (EAE) of soy sauce was separated using flash column chromatography, crystallized, and analyzed by nuclear magnetic resonance (NMR), single-crystal X-ray diffraction (SC-XRD), and mass spectroscopy. Dihydrocanadensolide (DHC), an antiulcer agent, was identified in a food for the first time. The natural stereostructure of DHC, which remained controversial for several decades, was determined as (3S,3aS,6R,6aR)-6-butyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione using SC-XRD analysis. Kojic acid (KA) and vanillic acid (VA) were also identified from EAE as bioactive metabolic products of fungi and yeasts. Moreover, a new polymorphic form of KA was determined by SC-XRD.
2. Intramolecular cyclopropanation of glycals: studies toward the synthesis of canadensolide, sporothriolide, and xylobovide
V Lynch, M Yu, B L Pagenkopf Org Lett . 2001 Aug 9;3(16):2563-6. doi: 10.1021/ol016239h.
[reaction: see text] The first examples of copper-catalyzed intramolecular cyclopropanations of glycal-derived diazoacetates are reported. The new cyclopropanes are converted into advanced intermediates for the synthesis of bislactone natural products. Synthetic highlights include the selective monodeprotection of a di-tert-butylsilylene ether and a zinc-mediated ring opening cascade reaction.
3. Addition/oxidative rearrangement of 3-furfurals and 3-furyl imines: new approaches to substituted furans and pyrroles
Michael H Kerrigan, Ann Rowley Kelly, Patrick J Walsh J Am Chem Soc . 2008 Mar 26;130(12):4097-104. doi: 10.1021/ja710988q.
Furans and pyrroles are important synthons in chemical synthesis and are commonly found in natural products, pharmaceutical agents, and materials. Introduced herein are three methods to prepare 2-substituted 3-furfurals starting from 3-furfural, 3-bromofuran, and 3-vinylfurans. Addition of a variety of organolithium, Grignard, and organozinc reagents (M-R) to 3-furfural provides 3-furyl alcohols in high yields. Treatment of these intermediates with NBS initiates a novel oxidative rearrangement that results in the installation of the R group in the 2 position of the 2-substituted 3-furfurals. Likewise, metalation of 3-bromofuran with n-BuLi and addition to benzaldehyde provides a furyl alcohol that is converted to 2-phenyl 3-furfural upon oxidative rearrangement. Enantioenriched disubstituted furans can be prepared starting with the Sharpless asymmetric dihydroxylation of 3-vinylfurans. The resulting enantioenriched diols undergo the oxidative rearrangement to furnish enantioenriched 2-substituted 3-furfurals with excellent transfer of asymmetry. This later method has been applied to the enantioselective preparation of an intermediate in Honda's synthesis of the natural product (-)-canadensolide. Mechanistic studies involving deuterium-labeled furyl alcohol suggest that the oxidative rearrangement proceeds through an unsaturated 1,4-dialdehyde intermediate. The alcohol then cyclizes onto an aldehyde, resulting in the elimination of water and rearomatization. On the basis of this proposed mechanism, we found that 3-furyl imines undergo the addition of organometallic reagents to provide furyl sulfonamides. Under the oxidative rearrangement conditions, 2-substituted 3-formyl pyrroles are formed, providing a novel route to these heterocycles. In contrast to the metalation of heterocycles, which often lead to mixtures of regioisomeric products, these new oxidative rearrangements of furyl alcohols and furyl sulfonamides generate only one regioisomer in each case.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
