(R)-Usnic acid

Inquiry

For Research Use Only.

Category

Phenols

Cat.No.

NP4631

CAS

7562-61-0

Product Name

(R)-Usnic acid

Structure

Product Details

Description

It is a naturally occurring dibenzofuran derivative found in several lichen species. It is a potent antibiotic effective against Gram-positive bacteria, Mycobacterium tuberculosis, and some pathogenic fungi. It exhibits activities of antiviral, antiprotozoal, antimitotic, anti-inflammatory, and analgesic.

Synonyms

1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-, (9bR)-; (9bR)-2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione; (9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione; Usnic acid, (R)-; (+)-Usnic acid; (+)-Usninic acid; d-Usnic acid; d-Usninic acid; NSC 685596; Usnic acid, (+)-

IUPAC Name

(9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione

Molecular Weight

344.32

Molecular Formula

C18H16O7

Canonical SMILES

CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O

InChI

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/h5,11,22-23H,1-4H3/t11?,18-/m0/s1

InChIKey

CUCUKLJLRRAKFN-MCEAHNFKSA-N

Boiling Point

594.8±50.0°C at 760 mmHg

Melting Point

206°C

Purity

>98%

Density

1.49±0.1 g/cm3

Solubility

Soluble in DMSO (Slightly), Methanol (Slightly)

Appearance

Yellow powder

Storage

Store at -20°C

Alpha

488 º (c=0.4, CHCl3)

BRN

96698

EINECS

231-456-0

3-10

Hazard Class

Hazard Codes

IRRITANT

HS Code

29329990

pKa

4.00±0.40(Predicted)

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 °C, recrystallize twice with ethyl acetate, and the obtained relatively pure pale yellow needle crystal is the fine usnic acid.

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%).

Refractive Index

1.4790 (estimate)

Risk Statements

RTECS

HP5295050

Safety Statements

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.

Water Solubility

Partly soluble in water. Soluble in acetone, ethanol, chloroform and furfural.

WGK Germany

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