Vulpinic acid | CAS# 521-52-8 | Lichen Metabolite

MedKoo Cat#: 574055 | Name: Vulpinic acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Vulpinic acid

CAS#521-52-8

Theoretical Analysis

MedKoo Cat#: 574055

Name: Vulpinic acid

CAS#: 521-52-8

Chemical Formula: C19H14O5

Exact Mass: 322.0841

Molecular Weight: 322.32

Elemental Analysis: C, 70.80; H, 4.38; O, 24.82

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 205.00
50mg	USD 360.00
100mg	USD 550.00
250mg	USD 1,000.00

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Related CAS #

No Data

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

Instruction

View handling instruction

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.

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

1: Alkan AH, Ensoy M, Cansaran-Duman D. A new therapeutic strategy for luminal A-breast cancer treatment: vulpinic acid as an anti-neoplastic agent induces ferroptosis and apoptosis mechanisms. Med Oncol. 2024 Aug 19;41(9):229. doi: 10.1007/s12032-024-02473-8. PMID: 39158808. 2: Wang T, Tang C, Xiao M, Cao Z, He M, Qi J, Li Y, Li X. Effect of Air Drying on the Metabolic Profile of Fresh Wild and Artificial Cordyceps sinensis. Foods. 2023 Dec 21;13(1):48. doi: 10.3390/foods13010048. PMID: 38201076; PMCID: PMC10778509. 3: Desmarets L, Millot M, Chollet-Krugler M, Boustie J, Camuzet C, François N, Rouillé Y, Belouzard S, Tomasi S, Mambu L, Séron K. Lichen or Associated Micro- Organism Compounds Are Active against Human Coronaviruses. Viruses. 2023 Aug 31;15(9):1859. doi: 10.3390/v15091859. PMID: 37766264; PMCID: PMC10536056. 4: Budak B, Kalın ŞN, Yapça ÖE. Antiproliferative, antimigratory, and apoptotic effects of diffractaic and vulpinic acids as thioredoxin reductase 1 inhibitors on cervical cancer. Naunyn Schmiedebergs Arch Pharmacol. 2024 Mar;397(3):1525-1535. doi: 10.1007/s00210-023-02698-w. Epub 2023 Sep 1. PMID: 37658214. 5: Kalın ŞN, Altay A, Budak H. Inhibition of thioredoxin reductase 1 by vulpinic acid suppresses the proliferation and migration of human breast carcinoma. Life Sci. 2022 Dec 1;310:121093. doi: 10.1016/j.lfs.2022.121093. Epub 2022 Oct 18. PMID: 36270425. 6: Ureña-Vacas I, González-Burgos E, Divakar PK, Gómez-Serranillos MP. Lichen Extracts from Cetrarioid Clade Provide Neuroprotection against Hydrogen Peroxide-Induced Oxidative Stress. Molecules. 2022 Oct 2;27(19):6520. doi: 10.3390/molecules27196520. PMID: 36235056; PMCID: PMC9573381. 7: Yangın S, Cansaran-Duman D, Eskiler GG, Aras S. The molecular mechanisms of vulpinic acid induced programmed cell death in melanoma. Mol Biol Rep. 2022 Sep;49(9):8273-8280. doi: 10.1007/s11033-022-07619-3. Epub 2022 Aug 12. PMID: 35960408. 8: Paguirigan JA, Liu R, Im SM, Hur JS, Kim W. Evaluation of Antimicrobial Properties of Lichen Substances against Plant Pathogens. Plant Pathol J. 2022 Feb;38(1):25-32. doi: 10.5423/PPJ.OA.12.2021.0176. Epub 2022 Feb 1. PMID: 35144359; PMCID: PMC8831355. 9: Wu Y, Gan D, Leng X, He W, Zhang X, Li C, Gu X, Hu Y, Du S, Han Y. Anti- ageing and Anti-lung Carcinoma Effects of Vulpinic Acid and Usnic Acid Compounds and Biological Investigations with Molecular Modeling Study. J Oleo Sci. 2022;71(2):247-255. doi: 10.5650/jos.ess21276. PMID: 35110467. 10: Mohammadi M, Bagheri L, Badreldin A, Fatehi P, Pakzad L, Suntres Z, van Wijnen AJ. Biological Effects of Gyrophoric Acid and Other Lichen Derived Metabolites, on Cell Proliferation, Apoptosis and Cell Signaling pathways. Chem Biol Interact. 2022 Jan 5;351:109768. doi: 10.1016/j.cbi.2021.109768. Epub 2021 Dec 3. PMID: 34864007; PMCID: PMC8808380. 11: Cansaran-Duman D, Yangın S, Çolak B. The role of vulpinic acid as a natural compound in the regulation of breast cancer-associated miRNAs. Biol Res. 2021 Nov 7;54(1):37. doi: 10.1186/s40659-021-00360-4. PMID: 34743742; PMCID: PMC8574026. 12: Demir Y, Ceylan H, Türkeş C, Beydemir Ş. Molecular docking and inhibition studies of vulpinic, carnosic and usnic acids on polyol pathway enzymes. J Biomol Struct Dyn. 2022;40(22):12008-12021. doi: 10.1080/07391102.2021.1967195. Epub 2021 Aug 23. PMID: 34424822. 13: Cansaran-Duman D, Guney Eskiler G, Colak B, Sozen Kucukkara E. Vulpinic acid as a natural compound inhibits the proliferation of metastatic prostate cancer cells by inducing apoptosis. Mol Biol Rep. 2021 Aug;48(8):6025-6034. doi: 10.1007/s11033-021-06605-5. Epub 2021 Jul 30. PMID: 34331181. 14: Ulus G. Antiangiogenic properties of lichen secondary metabolites. Phytother Res. 2021 Jun;35(6):3046-3058. doi: 10.1002/ptr.7023. Epub 2021 Feb 15. PMID: 33587324.