(+)-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
- Molecular Weight:
- 344.32
- MDL Number:
- MFCD00016878
- MOL File:
- 7562-61-0.mol
- MSDS File:
- SDS
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) |
FDA UNII | 663456969I |
(+)-Usniacin price More Price(48)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | 329967 | (+)-Usnic acid 98% | 7562-61-0 | 5g | $63.1 | 2024-03-01 | Buy |
Sigma-Aldrich | 329967 | (+)-Usnic acid 98% | 7562-61-0 | 25g | $110 | 2024-03-01 | Buy |
TCI Chemical | U0023 | (+)-Usnic Acid >98.0%(HPLC)(T) | 7562-61-0 | 1g | $25 | 2024-03-01 | Buy |
TCI Chemical | U0023 | (+)-Usnic Acid >98.0%(HPLC)(T) | 7562-61-0 | 25g | $180 | 2024-03-01 | Buy |
Alfa Aesar | H56612 | (+)-Usnic acid, 98% | 7562-61-0 | 5g | $55.65 | 2024-03-01 | Buy |
(+)-Usniacin Chemical Properties,Uses,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 acts as an antibacterial and antifungal agent, and are often seen used in cosmetics and facial application chemicals.
Uses
Usnic acid is used as fragrance; preservative in deodorants; in anti ac ne formulations; antibiotic for topical application.
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.
(+)-Usniacin Preparation Products And Raw materials
Raw materials
Preparation Products
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
BINBO BIOLOGICAL CO.,LTD | +8618629063126 | info@binbobiological.com | China | 346 | 58 |
Nanjing Finetech Chemical Co., Ltd. | 025-85710122 17714198479 | sales@fine-chemtech.com | CHINA | 885 | 55 |
career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29888 | 58 |
Nanjing Dolon Biotechnology Co.,Ltd. | 18905173768 | sales@dolonchem.com | CHINA | 2972 | 58 |
Xi'an Kono chem co., Ltd., | 029-86107037 13289246953 | info@konochemical.com | China | 2995 | 58 |
Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 22968 | 58 |
Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | sales@chemdad.com | China | 39916 | 58 |
SIMAGCHEM CORP | +86-13806087780 | sale@simagchem.com | China | 17367 | 58 |
Wuhan ChemNorm Biotech Co.,Ltd. | +86-27-8439 4403 18971486879 | sales@chemnorm.com | CHINA | 2935 | 58 |
Hefei TNJ Chemical Industry Co.,Ltd. | +86-0551-65418671 +8618949823763 | sales@tnjchem.com | China | 34571 | 58 |
View Lastest Price from (+)-Usniacin manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
---|---|---|---|---|---|---|---|---|
2024-09-18 | (+)-Usniacin
7562-61-0
|
US $0.00 / KG | 1KG | 98% | 200kg/month | WUHAN FORTUNA CHEMICAL CO., LTD | ||
2024-04-29 | (+)-Usniacin
7562-61-0
|
US $0.00 / kg | 1kg | 98% | 1000 kg | BINBO BIOLOGICAL CO.,LTD | ||
2021-07-02 | (+)-Usnic acid 98%
7562-61-0
|
US $15.00-10.00 / KG | 1KG | 99%+ HPLC | Monthly supply of 1 ton | Zhuozhou Wenxi import and Export Co., Ltd |
- (+)-Usniacin
7562-61-0
- US $0.00 / KG
- 98%
- WUHAN FORTUNA CHEMICAL CO., LTD
- (+)-Usniacin
7562-61-0
- US $0.00 / kg
- 98%
- BINBO BIOLOGICAL CO.,LTD
- (+)-Usnic acid 98%
7562-61-0
- US $15.00-10.00 / KG
- 99%+ HPLC
- Zhuozhou Wenxi import and Export Co., Ltd