Pulvinic acid
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-05109 |
| CAS | 26548-70-9 |
| Molecular Weight | 308.28 |
| Molecular Formula | C18H12O5 |
Online Inquiry
Description
Pulvinic acid is a natural chemical pigment found in lichens.
Specification
| Synonyms | Pulvic acid; 2,4-Hexadienedioic acid, 3,4-dihydroxy-2,5-diphenyl-, γ-lactone (7CI); Benzeneacetic acid, α-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-, (E)- |
| IUPAC Name | (2E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetic acid |
| Canonical SMILES | C1=CC=C(C=C1)C2=C(C(=C(C3=CC=CC=C3)C(=O)O)OC2=O)O |
| InChI | InChI=1S/C18H12O5/c19-15-13(11-7-3-1-4-8-11)18(22)23-16(15)14(17(20)21)12-9-5-2-6-10-12/h1-10,19H,(H,20,21)/b16-14+ |
| InChI Key | CMFBGFRHPQTELQ-JQIJEIRASA-N |
Properties
| Appearance | Orange Powder |
| Boiling Point | 544.4°C at 760 mmHg |
| Melting Point | 216-217°C |
| Density | 1.475 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Vulpinic Acid Controls Stem Cell Fate toward Osteogenesis and Adipogenesis
Sang Ah Yi, Ki Hong Nam, Sil Kim, Hae Min So, Rhim Ryoo, Jeung-Whan Han, Ki Hyun Kim, Jaecheol Lee Genes (Basel). 2019 Dec 23;11(1):18. doi: 10.3390/genes11010018.
Vulpinic acid, a naturally occurring methyl ester of pulvinic acid, has been reported to exert anti-fungal, anti-cancer, and anti-oxidative effects. However, its metabolic action has not been implicated yet. Here, we show that vulpinic acid derived from a mushroom, Pulveroboletus ravenelii controls the cell fate of mesenchymal stem cells and preadipocytes by inducing the acetylation of histone H3 and α-tubulin, respectively. The treatment of 10T1/2 mesenchymal stem cells with vulpinic acid increased the expression of Wnt6, Wnt10a, and Wnt10b, which led to osteogenesis inhibiting the adipogenic lineage commitment, through the upregulation of H3 acetylation. By contrast, treatment with vulpinic acid promoted the terminal differentiation of 3T3-L1 preadipocytes into mature adipocytes. In this process, the increase in acetylated tubulin was accompanied, while acetylated H3 was not altered. As excessive generation of adipocytes occurs, the accumulation of lipid drops was not concentrated, but dispersed into a number of adipocytes. Consistently, the expressions of lipolytic genes were upregulated and inflammatory factors were downregulated in adipocytes exposed to vulpinic acid during adipogenesis. These findings reveal the multiple actions of vulpinic acid in two stages of differentiation, promoting the osteogenesis of mesenchymal stem cells and decreasing hypertrophic adipocytes, which can provide experimental evidence for the novel metabolic advantages of vulpinic acid.
2. In Silico Discovery of Novel Potent Antioxidants on the Basis of Pulvinic Acid and Coumarine Derivatives and Their Experimental Evaluation
Rok Martinčič, Janez Mravljak, Urban Švajger, Andrej Perdih, Marko Anderluh, Marjana Novič PLoS One. 2015 Oct 16;10(10):e0140602. doi: 10.1371/journal.pone.0140602. eCollection 2015.
A pigment from the edible mushroom Xerocomus badius norbadione A, which is a natural derivative of pulvinic acid, was found to possess antioxidant properties. Since the pulvinic acid represents a novel antioxidant scaffold, several other derivatives were recently synthetized and evaluated experimentally, along with some structurally related coumarine derivatives. The obtained data formed the basis for the construction of several quantitative structure-activity and pharmacophore models, which were employed in the virtual screening experiments of compound libraries and for the prediction of their antioxidant activity, with the goal of discovering novel compounds possessing antioxidant properties. A final prioritization list of 21 novel compounds alongside 8 established antioxidant compounds was created for their experimental evaluation, consisting of the DPPH assay, 2-deoxyribose assay, β-carotene bleaching assay and the cellular antioxidant activity assay. Ten novel compounds from the tetronic acid and barbituric acid chemical classes displayed promising antioxidant activity in at least one of the used assays, that is comparable to or even better than some standard antioxidants. Compounds 5, 7 and 9 displayed good activity in all the assays, and were furthermore effective preventers of oxidative stress in human peripheral blood mononuclear cells, which are promising features for the potential therapeutic use of such compounds.
3. The Total Synthesis of Chalcitrin
Ming Yang, Fangjie Yin, Haruka Fujino, Scott A Snyder J Am Chem Soc. 2019 Mar 20;141(11):4515-4520. doi: 10.1021/jacs.8b12612. Epub 2019 Mar 11.
The first total synthesis of the yellow pigment chalcitrin, a structurally distinct pulvinic acid dimer obtained from Chalciporous piperatus, has been achieved in 17 linear steps from commercially available materials. Key elements of the design include the use of a Au(I)-catalyzed Conia ene reaction and an N-heterocyclic carbene-mediated acyloin addition to rapidly fashion its unique polycyclic core, with the two high oxidation state side chains introduced in a single step via a late-stage double Stille coupling. Of note, many alternate designs based on differential final couplings failed, likely because of the hindered nature of the core. In addition, significant challenges in final natural product characterization in terms of matching NMR spectra were experienced; our studies reveal that the originally characterized material was its carboxylate salt form not its free acid.
Recommended Products
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-01825 | Loganin | Inquiry |
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 ╳
