|
|
| | VULPINIC ACID Basic information |
| Product Name: | VULPINIC ACID | | Synonyms: | 3,4-DIHYDROXY-2,5-DIPHENYL-2,4-HEXA-DIENEDIOIC ACID METHYL ESTER 3,6-LACTONE;VULPIC ACID;VULPINIC ACID;(3-hydroxy-5-oxo-4-phenyl-2(5h)-furylidene)phenyl-aceticacimethylester;2,4-hexadienedioicacid,3,4-dihydroxy-2,5-diphenyl-,mono-gamma-lactone,met;alpha)-furanaceticacid,3-hydroxy-5-oxo-alpha,4-diphenyl-delta(sup2(5hmet;PULVINIC ACID METHYL ESTER;methyl 2-(3,5-dioxo-4-phenyl-2-furylidene)-2-phenylacetate | | CAS: | 521-52-8 | | MF: | C19H14O5 | | MW: | 322.31 | | EINECS: | 208-314-1 | | Product Categories: | Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Various Metabolites and Impurities | | Mol File: | 521-52-8.mol |  |
| | VULPINIC ACID Chemical Properties |
| Melting point | 146-148°C | | storage temp. | -20°C Freezer | | solubility | Acetonitrile (Slightly, Heated), Chloroform (Slightly), DMSO (Slightly) | | form | Solid | | color | Yellow | | LogP | 2.540 (est) |
| Risk Statements | 28 | | Safety Statements | 1-22-45 | | RIDADR | 3172 | | Toxicity | mouse,LD50,intraperitoneal,75mg/kg (75mg/kg),Acta Pharmacologica et Toxicologica. Vol. 2, Pg. 109, 1946. |
| | VULPINIC ACID Usage And Synthesis |
| Description | Vulpinic acid is a lichen metabolite that has been found in L. vulpina and has diverse biological activities. It is active against C. perfringens, B. vulgatus, B. fragilis, B. loescheii, P. acnes, E. faecium, and methicillin-susceptible and -resistant S. aureus (MICs = 4-16 μg/ml). Vulpinic acid (25-800 μM) prevents UVB-induced apoptosis, cytotoxicity, and cytoskeletal modifications in HaCaT human keratinocytes. It also increases scratch wound healing of HaCaT cells. Vulpinic acid (15 μM) reduces hydrogen peroxide-induced production of reactive oxygen species (ROS) and cytotoxicity in human umbilical vein endothelial cells (HUVECs). | | Chemical Properties | Yellow Solid | | Uses | antiinflammatory, antibacterial, plant growth inhibitor | | Uses | A lichen metabolite with anti-inflammatory properties. | | Definition | ChEBI: Vulpinic acid is a butenolide. | | References | [1] M LAUTERWEIN. In vitro activities of the lichen secondary metabolites vulpinic acid, (+)-usnic acid, and (-)-usnic acid against aerobic and anaerobic microorganisms.[J]. Antimicrobial Agents and Chemotherapy, 1995, 39 11: 2541-2543. DOI: 10.1128/aac.39.11.2541
[2] MEHMET VAROL. Photoprotective Activity of Vulpinic and Gyrophoric Acids Toward Ultraviolet B-Induced Damage in Human Keratinocytes.[J]. Phytotherapy Research, 2016, 30 1: 9-15. DOI: 10.1002/ptr.5493
[3] BRUNO BURLANDO. Antiproliferative effects on tumour cells and promotion of keratinocyte wound healing by different lichen compounds.[J]. Planta medica, 2009, 75 6: 607-613. DOI: 10.1055/s-0029-1185329
[4] E SAHIN. Vulpinic acid, a lichen metabolite, emerges as a potential drug candidate in the therapy of oxidative stress-related diseases, such as atherosclerosis.[J]. Human & Experimental Toxicology, 2019, 38 6: 675-684. DOI: 10.1177/0960327119833745 |
| | VULPINIC ACID Preparation Products And Raw materials |
|