Skip to Content
Merck
All Photos(2)

Key Documents

329967

Sigma-Aldrich

(+)-Usnic acid

98%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C18H16O7
CAS Number:
Molecular Weight:
344.32
Beilstein:
96698
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

powder

optical activity

[α]25/D +488°, c = 0.7% in chloroform

mp

201-203 °C (lit.)

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

Looking for similar products? Visit Product Comparison Guide

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

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
Inhibitory Activity of (+)-Usnic Acid against Non-Small Cell Lung Cancer Cell Motility.
Yang Y, et al.
PLoS ONE, 11(1), e0146575-e0146575 (2016)
Michal Goga et al.
Ecology and evolution, 8(5), 2781-2787 (2018-03-14)
Lichens and mosses often share the same environmental conditions where they compete for substrate and other essential factors. Lichens use secondary metabolites as allelochemicals to repel surrounding plants and potential rivals. In mosses, endoreduplication leads to the occurrence of various
Kunal Kumar et al.
Chemico-biological interactions, 315, 108898-108898 (2019-11-13)
Usnic acid, a dibenzofuran derivative found in many lichen species, is reported to have anticancer activity against human gastric cancer. We investigated the molecular alterations associated with anticancer effects of usnic acid against human gastric adenocarcinoma AGS and gastric carcinoma
Antibacterial activity of lichen secondary metabolite usnic acid is primarily caused by inhibition of RNA and DNA synthesis.
Maciag-Dorszynska M, et al.
FEMS Microbiology Letters, 353(1), 57-62 (2014)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service