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Merck

329967

(+)-Usnic acid

98%

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C18H16O7
Numéro CAS:
7562-61-0
Poids moléculaire :
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

Principaux documents

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InChI key

ICTZCAHDGHPRQR-GOSISDBHSA-N

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

SMILES string

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

assay

98%

form

powder

optical activity

[α]25/D +488°, c = 0.7% in chloroform

mp

201-203 °C (lit.)

functional group

ketone

Quality Level

100

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Catégories apparentées

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
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
MKCZ2884
MKCN5004
MKCK3869
MKCD9733
MKBX6051V

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

  5. Do you offer any interpretation of the IR spectrum of Product 329967, (+)-Usnic acid?

    Although we do not perform any detailed analysis of IR spectrum as part of our routine QC testing for this product, we can say that the broad stretch around  3000 cm-1is due to hydrogen-bonded hydroxyl (OH) groups and the band at 1700 cm-1 is due to the carbonyl (C=O).

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