(+)-Usniacin

(+)-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 Structure
(+)-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
pka4.00±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
LogP1.270 (est)
CAS DataBase Reference7562-61-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 36
WGK Germany 3
RTECS HP5295050
3-10
HazardClass IRRITANT
HS Code 29329990
MSDS Information
ProviderLanguage
SigmaAldrich English
(+)-Usniacin Usage And Synthesis
PreparationWeigh 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.
UsesUsnic Acid acts as an antibacterial and antifungal agent, and are often seen used in cosmetics and facial application chemicals.
UsesUsnic 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.
DefinitionChEBI: (-)-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 Activitymic: 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 allergensUsnic 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 MethodsThis 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
3-Methylphenethyl alcohol 4,4'-Diacetylbiphenyl N-ACETYL-L-TYROSINE ETHYL ESTER 3-(3,5-DIMETHYLPHENYL)-1-PROPENE Ethyl 2-(Chlorosulfonyl)acetate Ascoric Acid 2-tert-Butyl-6-methylphenol 2,4,6-TRIHYDROXY-1,3-DIMETHYL BENZENE Tetraacetylethylenediamine 2,4-Dihydroxy-3-methylbenzaldehyde USNIACIN,Usnein,Usniacin,Usninicacid,USNIACIN,Usnein,Usniacin,Usninicacid 5-ETHYL-2-HYDROXY-BENZALDEHYDE 5'-ETHYL-2'-HYDROXYACETOPHENONE Dimethyl sebacate phosphoric acid 2,6-DIMETHYLANISOLE 1-(3-ALLYL-2,6-DIHYDROXYPHENYL)ETHAN-1-ONE (+)-Usniacin

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