(±)-Usnic acid

Names

[ CAS No. ]:
125-46-2

[ Name ]:
(±)-Usnic acid

[Synonym ]:
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
1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-

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]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[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

[ Storage condition ]:
2-8C

MSDS

Click to get detail MSDS

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%