| Identification | More | [Name]
(+)-Usniacin | [CAS]
7562-61-0 | [Synonyms]
2,6-DIACETYL-7,9-DIHYDROXY-8,9B-DIMETHYLDIBENZOFURAN-1,3(2H,9BH)-DIONE
D-2,6-DIACETYL-7,9-DIHYDROXY-8,9BETA-DIMETHYL-1,3[2H,9BH]-DIBENZOFURANDIONE
D-USNIC ACID
TIMTEC-BB SBB006458
(+)-USNEIN
(+)-USNIACIN
(+)-USNIC ACID
USNIC ACID, (+)-
(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
6-diacetyl-8,9b-dimethyl-1,7,9-trihydroxy-d-3(9bh)-dibenzofuranon
d-usninicacid
(+)-Usnic acid from Usnea dasypoga
plus-usnic acid
(9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-(2H,9bH)-dibenzofuran-1,3-dione
(R)-Usnicacid
(USNEA DASYPOGA EXTRACT)(+) USNIC ACID 98%
DIFFRACTIC ACID(SH)
(+)-Usnein | [EINECS(EC#)]
231-456-0 | [Molecular Formula]
C18H16O7 | [MDL Number]
MFCD00016878 | [Molecular Weight]
344.32 | [MOL File]
7562-61-0.mol |
| Chemical Properties | Back Directory | [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. ]
2-8°C | [solubility ]
almost transparency in Chloroform | [form ]
powder to crystal | [pka]
4.00±0.40(Predicted) | [color ]
Light orange to Yellow to Green | [Optical Rotation]
[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 | [InChI]
1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,22-24H,1-4H3/t18-/m1/s1 | [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. | [InChIKey]
ICTZCAHDGHPRQR-GOSISDBHSA-N | [SMILES]
C[C@](C1=C(O)C(C)=C(O)C(C(C)=O)=C1O2)(C(C3C(C)=O)=O)C2=CC3=O | [LogP]
1.270 (est) | [CAS DataBase Reference]
7562-61-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
HP5295050
| [F ]
3-10 | [HazardClass ]
IRRITANT | [HS Code ]
29329990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Questions And Answer | Back Directory | [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. |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Usnea diffracta Vain. | [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.
| [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. | [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]
This substance 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. | [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, kivan? 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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