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329967

Sigma-Aldrich

(+)-Usninsäure

98%

Synonym(e):

2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-(2H,9bH)-dion

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€ 59,50
25 G
€ 104,00

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5 G
€ 59,50
25 G
€ 104,00

About This Item

Empirische Formel (Hill-System):
C18H16O7
CAS-Nummer:
Molekulargewicht:
344.32
Beilstein:
96698
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.22

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Qualitätsniveau

Assay

98%

Form

powder

Optische Aktivität

[α]25/D +488°, c = 0.7% in chloroform

mp (Schmelzpunkt)

201-203 °C (lit.)

Funktionelle Gruppe

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

InChIKey

ICTZCAHDGHPRQR-GOSISDBHSA-N

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Allgemeine Beschreibung

(+)-Usnic acid is a bioactive compound mainly found as a secondary metabolite in lichens.[1]

Anwendung

(+)-Usnic acid has been used to study the following:
  • The mechanism of its antimicrobial activity in bacterial cells.[2]
  • Its ability as an antibiofilm agent against Group A Streptococci (GAS).[1]
  • Its ability as a potent anti-virulent compound against Candida albicans.[3]
  • The mechanism of its toxic effect on hepatocytes.[4]
  • Its ability to inhibit the motility of human lung cancer cells.[5]

Piktogramme

Exclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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Kunden haben sich ebenfalls angesehen

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)
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)
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

Questions

1–2 of 2 Questions  
  1. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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.

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

    1 answer
    1. 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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