(±)-Usnic acid

Modify Date: 2026-07-23 19:22:42

(±)-Usnic acid Structure
(±)-Usnic acid structure
Common Name (±)-Usnic acid
CAS Number 125-46-2 Molecular Weight 344.315
Density 1.5±0.1 g/cm3 Boiling Point 594.8±50.0 °C at 760 mmHg
Molecular Formula C18H16O7 Melting Point 200°C
MSDS Chinese USA Flash Point 219.1±23.6 °C

 Use of (±)-Usnic acid


Usnic acid, a lichen-derived secondary metabolite, has a unique dibenzofuran skeleton. Usnic acid has excellent anticancer and antimicrobial properties. Usnic acid significantly inhibits RANKL-mediated osteoclast formation and function by reducing the transcriptional and translational expression of NFATc1[1].

 Names

Name usnic acid
Synonym More Synonyms

 (±)-Usnic acid Biological Activity

Description Usnic acid, a lichen-derived secondary metabolite, has a unique dibenzofuran skeleton. Usnic acid has excellent anticancer and antimicrobial properties. Usnic acid significantly inhibits RANKL-mediated osteoclast formation and function by reducing the transcriptional and translational expression of NFATc1[1].
Related Catalog
References

[1]. Kim KJ, et al. Effect of Usnic Acid on Osteoclastogenic Activity. J Clin Med. 2018 Oct 12;7(10). pii: E345.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 594.8±50.0 °C at 760 mmHg
Melting Point 200°C
Molecular Formula C18H16O7
Molecular Weight 344.315
Flash Point 219.1±23.6 °C
Exact Mass 344.089600
PSA 117.97000
LogP 2.68
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.643
InChIKey CUCUKLJLRRAKFN-UHFFFAOYSA-N
SMILES CC(=O)c1c(O)c(C)c(O)c2c1OC1=CC(=O)C(C(C)=O)C(=O)C12C
Storage condition 2-8C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HP5270000
CHEMICAL NAME :
1,3(2H,9bH)-dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-
CAS REGISTRY NUMBER :
125-46-2
LAST UPDATED :
199701
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C18-H16-O7
MOLECULAR WEIGHT :
344.34
WISWESSER LINE NOTATION :
T B656 CV EV HO FU BHT&&J B1 DV1 JV1 KQ L1 MQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
75 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Mammal - species unspecified Cells - not otherwise specified
DOSE/DURATION :
3750 ug/L
REFERENCE :
PHMCAA Pharmacologist. (American Soc. for Pharmacology and Experimental Therapeutics, 9650 Rockville Pike, Bethesda, MD 20014) V.1- 1959- Volume(issue)/page/year: 12,280,1970

 Safety Information

Hazard Codes Xn:Harmful;
Risk Phrases R22
Safety Phrases S22-S24/25
RTECS HP5270000
HS Code 2917399090

 Customs

HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 (±)-Usnic acidBioassay

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Name: ERK5 transcriptional activity HTS
Source: 24565
Target: N/A
External Id: ERK5 transcriptional activity-HTS
Name: qHTS for Inhibitors of human tyrosyl-DNA phosphodiesterase 1 (TDP1): qHTS in cells in...
Source: NCGC
Target: TDP1 protein [Homo sapiens]
External Id: TDP1100
Name: qHTS for Stage-Specific Inhibitors of Vaccinia Orthopoxvirus: mCherry Reporter Primar...
Source: NCGC
Target: 67.9K protein [Vaccinia virus]
External Id: Vaccinia-p2mCherry
Name: qHTS for Inhibitors of human tyrosyl-DNA phosphodiesterase 1 (TDP1): qHTS in cells in...
Source: NCGC
Target: TDP1 protein [Homo sapiens]
External Id: TDP1101
Name: Spectrum HTS for Inhibitors of Aerobactin Synthetase IucA
Source: 23265
Target: IucA Synthetase from hypervirulent Klebsiella pneumoniae hvKP1
External Id: IucA Pilot Assay Spectrum Library
Name: The chemical genetic matrix (CGM) dataset as reported in Wildenhain et al. (2015) Pre...
Source: 11924
Target: N/A
External Id: CGM data for Cell Systems paper Dec 2015
Name: qHTS for Stage-Specific Inhibitors of Vaccinia Orthopoxvirus: Venus Reporter Primary ...
Source: NCGC
Target: 67.9K protein [Vaccinia virus]
External Id: Vaccinia-p2Venus
Name: Cell cycle arrest in human HeLa cells assessed as accumulation of cells at G2/M phase...
Source: ChEMBL
Target: HeLa
External Id: CHEMBL4336073
Name: qHTS for Inhibitors of binding or entry into cells for Marburg Virus
Source: NCGC
Target: gene 4 small orf - Marburg virus
External Id: VSVM-OFFLINE
Name: qHTS for Inhibitors of binding or entry into cells for Lassa Virus
Source: NCGC
Target: N/A
External Id: VSVL-OFFLINE
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 Synonyms

Usnic acid
MFCD00065294
EINECS 231-456-0
(±)-Usnic acid
2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bH)-dione
2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione
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