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Merck

329967

Sigma-Aldrich

(+)-Usnic acid

98%

Sinónimos:

(+)-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

Fórmula empírica (notación de Hill):
C18H16O7
Número de CAS:
Peso molecular:
344.32
Beilstein/REAXYS Number:
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.)

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

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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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Los clientes también vieron

Usnic acid inhibits biofilm formation and virulent morphological traits of Candida albicans.
Nithyanand P, et al.
Microbiological research, 179, 20-28 (2015)
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)
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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