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)

Safety Information

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

A lichen metabolite with anti-inflammatory properties.

Uses

antiinflammatory, antibacterial, plant growth inhibitor

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

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