7562-61-0 Usage
Description
(+)-Usniacin, also known as Usnic acid, is a naturally occurring compound with a unique molecular structure. It is characterized by the presence of dibenzofuran and xanthone moieties, which contribute to its diverse range of biological activities. (+)-Usniacin exhibits antimicrobial, anti-inflammatory, and anticancer properties, making it a versatile compound with potential applications in various industries.
Uses
Used in Cosmetics and Personal Care Industry:
(+)-Usniacin is used as a fragrance and preservative in deodorants due to its pleasant scent and ability to inhibit the growth of bacteria and fungi. It is also used in anti-acne formulations for its anti-inflammatory and antimicrobial properties, which help reduce inflammation and prevent the growth of acne-causing bacteria.
Used in Topical Antibiotic Formulations:
(+)-Usniacin is used as an antibiotic for topical application, particularly in the treatment of skin infections caused by bacteria and fungi. Its broad-spectrum antimicrobial activity makes it an effective agent for combating various types of skin infections.
Used in Cosmetics and Facial Application Chemicals:
(+)-Usniacin acts as an antibacterial and antifungal agent in cosmetics and facial application chemicals. Its ability to inhibit the growth of harmful microorganisms helps maintain skin health and prevent infections.
Used in Antimicrobial Research:
(+)-Usniacin has been used to study its antimicrobial activity in bacterial cells, providing insights into the mechanism by which it exerts its antibacterial effects. This research can contribute to the development of new antimicrobial agents and strategies to combat drug-resistant bacteria.
Used in Anti-biofilm Research:
(+)-Usniacin has been studied for its ability to act as an antibiofilm agent against Group A Streptococci (GAS). Biofilms are complex communities of microorganisms that are resistant to conventional antibiotics, making them a significant challenge in the treatment of infections. (+)-Usniacin's potential to disrupt biofilms could lead to new therapeutic approaches for treating biofilm-associated infections.
Used in Anti-virulent Compound Research:
(+)-Usniacin has been investigated for its ability to act as a potent anti-virulent compound against Candida albicans, a common fungal pathogen. By inhibiting the virulence factors of this fungus, (+)-Usniacin could help prevent or treat Candida infections.
Used in Hepatotoxicity Research:
(+)-Usniacin has been studied for its toxic effect on hepatocytes, which are liver cells responsible for various essential functions. Understanding the mechanism of its toxicity can help in the development of safer and more effective formulations of (+)-Usniacin for therapeutic use.
Used in Cancer Research:
(+)-Usniacin has been investigated for its ability to inhibit the motility of human lung cancer cells. This research could contribute to the development of new anticancer agents and strategies for the treatment of lung cancer.
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.
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.
