7562-61-0 Usage
Preparation
Weigh 5.0 g of chopped Usnea longiflora into a 500 mL flask, and extract with 75 mL of ethyl acetate for 2 times, 4 h each time, and combine the extracts. Suction filtration, concentrated to 1/6~1/8 of the original volume, naturally cooled, crystallized, filtered off the mother liquor, and dried at 80°C to obtain the crude usnic acid. 30 times the amount of benzene-ethanol (volume ratio 1:1) mixed solvent was added to the crude product, refluxed for 2 h, filtered while hot, the filtrate was concentrated to 1/5 of the original volume, and crystals were precipitated by cooling. Dry at 80 ℃, recrystallize twice with ethyl acetate, and the obtained relatively pure pale yellow needle crystal is the fine usnic acid.
Uses
Different sources of media describe the Uses of 7562-61-0 differently. You can refer to the following data:
1. Usnic acid is used as fragrance; preservative in deodorants; in anti ac ne formulations; antibiotic for topical application.
2. Usnic Acid acts as an antibacterial and antifungal agent, and are often seen used in cosmetics and facial application chemicals.
3. (+)-Usnic acid has been used to study the following:The mechanism of its antimicrobial activity in bacterial cells.Its ability as an antibiofilm agent against Group A Streptococci (GAS).Its ability as a potent anti-virulent compound against Candida albicans.The mechanism of its toxic effect on hepatocytes.Its ability to inhibit the motility of human lung cancer cells.
General Description
(+)-Usniacin is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG.
Biological Activity
mic: 0.05 μg/62.5 μl to 3.1 μg/62.5 μlmicroorganisms can colonize a wide variety of medical devices, putting patients at risk for systemic and local infectious complications, including local-site infections, endocarditis, and catheter-related bloodstream infections. (+)-usniacin is a secondary lichen metabolite that possesses antimicrobial activity against various planktonic gram-positive bacteria.
in vitro
(+)-usniacin showed antimicrobial activity against the same microorganisms as that of acetone extract. among the three analogues it was the most active one having quite low mic values. furthermore, (+)-usniacin did not show any activity against a. hydrophila and b. cereus whereas (d)-usnic acid did. on the other hand, (+)-usniacin was active against y. enterocolitica whereas (d)-usnic acid was not active [1].
references
[1] tay t, türk ao, yilmaz m, türk h, kivan? m. evaluation of the antimicrobial activity of the acetone extract of the lichen ramalina farinacea and its (+)-usnic acid, norstictic acid, and protocetraric acid constituents. z naturforsch c. 2004 may-jun;59(5-6):384-8.[2] ghione m, parrello d, grasso l. usnic acid revisited, its activity on oral flora. chemioterapia. 1988 oct;7(5):302-5.
Check Digit Verification of cas no
The CAS Registry Mumber 7562-61-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,5,6 and 2 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 7562-61:
(6*7)+(5*5)+(4*6)+(3*2)+(2*6)+(1*1)=110
110 % 10 = 0
So 7562-61-0 is a valid CAS Registry Number.
InChI:InChI=1/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,21-23H,1-4H3/t18-/m0/s1
7562-61-0Relevant articles and documents
The chemoenzymatic synthesis of usnic acid
Hawranik, Drew J.,Anderson, Kurtis S.,Simmonds, Reesa,Sorensen, John. L.
experimental part, p. 2383 - 2385 (2009/12/25)
Usnic acid, a highly functionalized dibenzofuran, is a polyketide secondary metabolite produced by several species of lichens. Synthesis of usnic acid from commercially available starting material was accomplished in two steps. The synthesis involves the methylation of phloracetophenone followed by oxidation with horseradish peroxidase. This work will lay the foundation for further biosynthetic studies on usnic acid.
