(+)-Usniacin
Preparation- Product Name
- (+)-Usniacin
- CAS No.
- 7562-61-0
- Chemical Name
- (+)-Usniacin
- Synonyms
- (+)-USNEIN;(+)-Usnein;(r)-usnicaci;(+)-USNIACIN;D-USNIC ACID;(+)-usnicaci;(+)-Usniacin;d-usninicacid;(R)-Usnicacid;plus-usnic acid
- CBNumber
- CB9422382
- Molecular Formula
- C18H16O7
- Formula Weight
- 344.32
- MOL File
- 7562-61-0.mol
(+)-Usniacin Property
- Melting point:
- 201-203 °C(lit.)
- alpha
- 488 º (c=0.4, CHCl3)
- Boiling point:
- 399.43°C (rough estimate)
- Density
- 1.2869 (rough estimate)
- refractive index
- 1.4790 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- almost transparency in Chloroform
- form
- powder to crystal
- pka
- 4.00±0.40(Predicted)
- color
- Light orange to Yellow to Green
- optical activity
- [α]25/D +488°, c = 0.7% in chloroform
- Water Solubility
- Partly soluble in water. Soluble in acetone, ethanol, chloroform and furfural.
- Merck
- 14,9893
- BRN
- 96698
- LogP
- 1.270 (est)
- CAS DataBase Reference
- 7562-61-0(CAS DataBase Reference)
N-Bromosuccinimide Price
- Product number
- 329967
- Product name
- (+)-Usnic acid
- Purity
- 98%
- Packaging
- 5g
- Price
- $63.1
- Updated
- 2024/03/01
- Product number
- 329967
- Product name
- (+)-Usnic acid
- Purity
- 98%
- Packaging
- 25g
- Price
- $110
- Updated
- 2024/03/01
- Product number
- U0023
- Product name
- (+)-Usnic Acid
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 1g
- Price
- $25
- Updated
- 2024/03/01
- Product number
- U0023
- Product name
- (+)-Usnic Acid
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 25g
- Price
- $180
- Updated
- 2024/03/01
- Product number
- H56612
- Product name
- (+)-Usnic acid, 98%
- Packaging
- 5g
- Price
- $55.65
- Updated
- 2024/03/01
(+)-Usniacin Chemical Properties,Usage,Production
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
Usnic acid is used as fragrance; preservative in deodorants; in anti ac ne formulations; antibiotic for topical application.
Uses
Usnic Acid acts as an antibacterial and antifungal agent, and are often seen used in cosmetics and facial application chemicals.
Uses
(+)-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.
Definition
ChEBI: (-)-usnic acid is the (-)-enantiomer of usnic acid. It has a role as an EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor. It is a conjugate acid of a (-)-usnic acid(2-). It is an enantiomer of a (+)-usnic acid.
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.
Contact allergens
Usnic acid is a component of lichens, also used as a topical antibiotic. Allergic contact dermatitis from lichens occurs mainly occupationally in forestry and horticultural workers, and in lichen pickers.
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].
Purification Methods
This very weak acid is the natural form which is recrystallised from Me2CO, MeOH or *C6H6. At 25o it is soluble in H2O (<0.01%), Me2CO (0.77%), EtOAc (0.88%), MeOCH2CH2OH (0.22%) and furfural (7.32%). [Curd & Robertson J Chem Soc 894 1937, Barton & Brunn J Chem Soc 603 1953, resolution: Dean et al. J Chem Soc 1250 1953, synthesis: Barton et al. J Chem Soc 538 1956, Beilstein 18/5 V 586.]
References
[1] tay t, türk ao, yilmaz m, türk h, kivanç 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.
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View Lastest Price from (+)-Usniacin manufacturers
- Product
- (+)-Usniacin 7562-61-0
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1000 kg
- Release date
- 2024-04-29
- Product
- (+)-Usniacin 7562-61-0
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 200kg/month
- Release date
- 2021-07-19
- Product
- (+)-Usnic acid 98% 7562-61-0
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-06-27