Pulvinic dilactone
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| Category | Others |
| Catalog number | BBF-05497 |
| CAS | 6273-79-6 |
| Molecular Weight | 290.27 |
| Molecular Formula | C18H10O4 |
| Purity | >90% |
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Specification
| Synonyms | Pulvinic anhydride; Pulvic acid lactone; Pulvic dilactone; Pulvic di-γ-lactone; Pulvinic acid lactone; Furo[3,2-b]furan-2,5-dione, 3,6-diphenyl-; NSC 35419 |
| IUPAC Name | 3,6-diphenylfuro[3,2-b]furan-2,5-dione |
| Canonical SMILES | C1=CC=C(C=C1)C2=C3C(=C(C(=O)O3)C4=CC=CC=C4)OC2=O |
| InChI | InChI=1S/C18H10O4/c19-17-13(11-7-3-1-4-8-11)15-16(22-17)14(18(20)21-15)12-9-5-2-6-10-12/h1-10H |
| InChI Key | KQTXUHHOWJUFOZ-UHFFFAOYSA-N |
Properties
| Boiling Point | 544.3°C at 760 mmHg |
| Density | 1.42 g/cm3 |
Reference Reading
1. Synthesis of pulvinic derivatives via TBAF-mediated regioselective opening of an unsymmetrical monoaromatic pulvinic dilactone
Damien Habrant, Antoine Le Roux, Stéphane Poigny, Stéphane Meunier, Alain Wagner, Charles Mioskowski J Org Chem. 2008 Dec 5;73(23):9490-3. doi: 10.1021/jo801817s.
The synthesis of the monoaromatic pulvinic dilactone 1 from a tetronic acid derivative is reported. The reaction of 1 with various amines was found to provide the two pulvinamides regioisomers 2a and 2b. Using tetrabutylammonium fluoride (TBAF) as an activator, pulvinamides 2a could be obtained with excellent regioselectivities and good yields. Additions of alcohols to 1 are also studied, leading to similar observations.
2. Raman spectroscopy of hot desert, high altitude epilithic lichens
Susana E Jorge Villar, Howell G M Edwards, Mark R D Seaward Analyst. 2005 May;130(5):730-7. doi: 10.1039/b501585e. Epub 2005 Mar 16.
Twenty-three highly-coloured lichen specimens belonging to the genera Candelariella, Aspicilia and Xanthoria from high altitude sites in the Atacama Desert, Chile, 2300-4500 metres, have been analysed non-destructively by Raman spectroscopy. The vibrational band assignments in the spectra of the specimens, which were still attached to their limestone or sandstone substrata, were accomplished by comparison with the chemical compositions obtained from wet chemical extraction methods. Carotenoids and chlorophyll were found in all specimens as major components and the characteristic spectral signatures of calcium oxalate monohydrate (whewellite) and dihydrate (weddellite) could be identified; chemical signatures were found for these materials even in lichen thalli growing on the non-calcareous substrata, indicating probably that the calcium was provided here from wind- or rain-borne sources. The Raman spectral biomarkers for a variety of protective biomolecules and accessory pigments such as usnic acid, calycin, pulvinic acid dilactone and rhizocarpic acid have been identified in the lichens, in broad agreement with the chemical extraction profiles. The present study indicates that some form of non-destructive taxonomic identification based on Raman spectroscopy was also possible.
3. Chemical constituents of the lichen, Candelaria concolor: a complete NMR and chemical degradative investigation
Daniel A Dias, Sylvia Urban Nat Prod Res. 2009;23(10):925-39. doi: 10.1080/14786410802682536.
A detailed chemical and spectroscopic investigation of the terrestrial lichen Candelaria concolor has yielded several lichenic metabolites belonging to the pulvinic acid series, as well as several depside derivatives including pulvinic dilactone (1), vulpinic acid (4) and calycin (5). The chemical transformation of 1 to pulvinic acid (3) is reported for the first time, as is the conversion of atranorin (6) to 5-chloroatranorin (7) and then finally to 5,5'-dichloroatranorin (8) under very mild conditions. Also presented is the complete 1D and 2D NMR assignment for compounds 1, 3, 4, 5 and 8, including partial NMR chemical shift assignments for the unstable depside (7). Previously, these metabolites had only been partially assigned by NMR spectroscopy.
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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 ╳
