| (+)-Usniacin Basic information |
| Preparation |
| 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 |
| 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 |
| CAS DataBase Reference | 7562-61-0(CAS DataBase Reference) |
| Safety Information |
| Hazard Codes | Xn |
| Risk Statements | 22 |
| Safety Statements | 36 |
| WGK Germany | 3 |
| RTECS | HP5295050 |
| F | 3-10 |
| HazardClass | IRRITANT |
| HS Code | 29329990 |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| (+)-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 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:
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| 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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