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329967

(+)-Usnic acid

Name: (+)-Usnic acid
Brand: ALDRICH

98%

Synonym(s):

(+)-Usnic acid from Usnea dasypoga, 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3(2H,9bH)-dione

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₁₆O₇

CAS Number:

7562-61-0

Molecular Weight:

344.32

UNSPSC Code:

12352106

NACRES:

NA.22

PubChem Substance ID:

24859825

EC Number:

231-456-0

Beilstein/REAXYS Number:

96698

MDL number:

MFCD00191041

Assay:

98%

Form:

powder

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Properties

Quality Level

100

assay

98%

form

powder

optical activity

[α]25/D +488°, c = 0.7% in chloroform

mp

201-203 °C (lit.)

functional group

ketone

SMILES string

C[C@](C1=C(O)C(C)=C(O)C(C(C)=O)=C1O2)(C(C3C(C)=O)=O)C2=CC3=O

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

InChI key

ICTZCAHDGHPRQR-GOSISDBHSA-N

Description

General description

(+)-Usnic acid is a bioactive compound mainly found as a secondary metabolite in lichens.

Application

(+)-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.

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pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Inhibitory Activity of (+)-Usnic Acid against Non-Small Cell Lung Cancer Cell Motility.

Yang Y, et al.

PLoS ONE, 11(1), e0146575-e0146575 (2016)

Usnic acid improves memory impairment after cerebral ischemia/reperfusion injuries by anti-neuroinflammatory, anti-oxidant, and anti-apoptotic properties.

Sohaila Erfani et al.

Iranian journal of basic medical sciences, 23(9), 1225-1231 (2020-09-24)

Cerebral ischemia/reperfusion causes complex pathological mechanisms that lead to brain tissue damage. Usnic acid is a lichen secondary metabolite that has many different biological properties including anti-inflammatory and anti-oxidant activities. Therefore, the objective of the current study was to investigate

Usnic acid, a lichen secondary metabolite inhibits Group A Streptococcus biofilms.

Nithyanand P, et al.

Antonie van Leeuwenhoek, 107(1), 263-272 (2015)

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Global Trade Item Number

SKU	GTIN
329967-25G	04061832985565
329967-5G	04061826725733