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| Product Name: | (+)-Usniacin | | Synonyms: | D-2,6-DIACETYL-7,9-DIHYDROXY-8,9BETA-DIMETHYL-1,3[2H,9BH]-DIBENZOFURANDIONE;D-USNIC ACID;TIMTEC-BB SBB006458;(+)-USNEIN;(+)-USNIACIN;(r)-usnicaci;3(2h,9bh)-dibenzofurandione,2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-(9b;6-diacetyl-1,7,9-trihydroxy-8,9b-dimethyl-d-3(9bh)-dibenzofuranon | | CAS: | 7562-61-0 | | MF: | C18H16O7 | | MW: | 344.32 | | EINECS: | 231-456-0 | | Product Categories: | Inhibitors;Pharmaceutical Raw Materials;Plant Oils, Toxins, Phenolic Acids & Derivatives | | Mol File: | 7562-61-0.mol |  |
| | (+)-Usniacin Chemical Properties |
| 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 | | pka | 4.00±0.40(Predicted) | | form | powder to crystal | | 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) |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 36 | | WGK Germany | 3 | | RTECS | HP5295050 | | F | 3-10 | | HazardClass | IRRITANT | | HS Code | 29329990 |
| | (+)-Usniacin Usage And Synthesis |
| 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 |
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