Vulpinic acid
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MedKoo CAT#: 574055

CAS#: 521-52-8

Description: Vulpinic acid is a lichen metabolite with 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. Vulpinic acid prevents UVB-induced apoptosis, cytotoxicity, and cytoskeletal modifications in HaCaT human keratinocytes. It also increases scratch wound healing of HaCaT cells. Vulpinic acid reduces hydrogen peroxide-induced production of reactive oxygen species (ROS) and cytotoxicity in human umbilical vein endothelial cells (HUVECs).

Chemical Structure

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Vulpinic acid
CAS# 521-52-8
Instruction

Theoretical Analysis

MedKoo Cat#: 574055
Name: Vulpinic acid
CAS#: 521-52-8
Chemical Formula: C19H14O5
Exact Mass: 322.08
Molecular Weight: 322.320
Elemental Analysis: C, 70.80; H, 4.38; O, 24.82

Price and Availability

Size Price Availability Quantity
10mg USD 205
50mg USD 360
100mg USD 550
250mg USD 1000
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Synonym: NSC 5897, Vulpinic acid

IUPAC/Chemical Name: methyl (Z)-2-(3-hydroxy-5-oxo-4-phenylfuran-2(5H)-ylidene)-2-phenylacetate

InChi Key: OMZRMXULWNMRAE-BMRADRMJSA-N

InChi Code: InChI=1S/C19H14O5/c1-23-18(21)15(13-10-6-3-7-11-13)17-16(20)14(19(22)24-17)12-8-4-2-5-9-12/h2-11,20H,1H3/b17-15+

SMILES Code: OC(/C(O1)=C(C(OC)=O)/C2=CC=CC=C2)=C(C3=CC=CC=C3)C1=O

Appearance: A crystalline solid

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 322.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1. Lauterwein, M., Oethinger, M., Belsner, K., et al. In vitro activities of the lichen secondary metabolites vulpinic acid, (+)-usnic acid, and (—)-usnic acid against aerobic and anaerobic microorganisms. Antimicrob. Agents Chemother. 39(11), 2541-2543 (1995).

2. Varol, M., Türk, A., Candan, M., et al. Photoprotective activity of vulpinic and gyrophoric acids toward ultraviolet B-induced damage in human keratinocytes. Phytother. Res. 30(1), 9-15 (2016).

3. Burlando, B., Ranzato, E., Volante, A., et al. Antiproliferative effects on tumour cells and promotion of keratinocyte wound healing by different lichen compounds. Planta. Med. 75(6), 607-613 (2009).

4. Sahin, E., Psav, S.D., Avan, I., et al. Vulpinic acid, a lichen metabolite, emerges as a potential drug candidate in the therapy of oxidative stress–related diseases, such as atherosclerosis. Hum. Exp. Toxicol. 38(6), 675-684 (2019).