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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

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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

Quality Level

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

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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’.

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Customers Also Viewed

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)
Usnic acid inhibits biofilm formation and virulent morphological traits of Candida albicans.
Nithyanand P, et al.
Microbiological research, 179, 20-28 (2015)
Xiaoge Geng et al.
Medical science monitor : international medical journal of experimental and clinical research, 24, 556-566 (2018-01-29)
BACKGROUND Usnic acid (UA), a secondary metabolite, is mainly derived from certain lichen species. Growing evidence suggests that UA has antitumor, anti-oxidative, anti-inflammatory, and other activities in a variety of cancer cells. However, the antitumor effect of UA in gastric
Monika Maciąg-Dorszyńska et al.
FEMS microbiology letters, 353(1), 57-62 (2014-02-28)
Usnic acid, a compound produced by various lichen species, has been demonstrated previously to inhibit growth of different bacteria and fungi; however, mechanism of its antimicrobial activity remained unknown. In this report, we demonstrate that usnic acid causes rapid and
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

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