USNIC ACID Chemical Properties

Melting point:

200°C

alpha 

D16 +509.4° (c = 0.697 in chloroform)

Boiling point:

399.43°C (rough estimate)

Density 

1.2869 (rough estimate)

refractive index 

495 ° (C=0.7, CHCl3)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMF:2.5(Max Conc. mg/mL);7.26(Max Conc. mM)

form 

A crystalline solid

pka

4.00±0.40(Predicted)

color 

White to yellow

Merck 

9893

LogP

2.880

CAS DataBase Reference

125-46-2(CAS DataBase Reference)

EPA Substance Registry System

Usnic acid (125-46-2)

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-50/53

Safety Statements 

22-24/25-61-60-45

RTECS 

HP5270000

Hazardous Substances Data

125-46-2(Hazardous Substances Data)

Toxicity

LD50 i.v. in mice: 25 mg/kg (Gottlieb, Shaw)

USNIC ACID Usage And Synthesis

Chemical Properties

Crystalline, yellow solid. Insoluble in water; slightly soluble in alcohol and ether.

Uses

Usnic acid is an enzyme inhibiting antitumor agent.

Uses

antibacterial

Uses

Usnic acid is a major metabolite from a number of lichen and fungal species and is perhaps one of the longest known microbial metabolites, first isolated in 1844. Usnic acid exhibits a broad range of biological activity, indeed it is easier to list the bioassays in which it does not exhibit activity. More often than not, potency is low and of limited value. Usnic acid is an important metabolite for dereplication in discovery research programs.

Definition

ChEBI: A member of the class of dibenzofurans that is dibenzo[b,d]furan-1(9bH)-one substituted by acetyl groups at positions 2 and 6, hydroxy groups at positions 3 and 7 and methyl groups at positions 8 and 9b.

Contact allergens

Usnic acid is a component of lichens, also used as a topical antibiotic. Allergic contact dermatitis from lichens occurs mainly occupationally in forestry and horticultural workers, and in lichen pickers.

Purification Methods

This very weak acid is the natural form which is recrystallised from Me2CO, MeOH or *C6H6. At 25o it is soluble in H2O (<0.01%), Me2CO (0.77%), EtOAc (0.88%), MeOCH2CH2OH (0.22%) and furfural (7.32%). [Curd & Robertson J Chem Soc 894 1937, Barton & Brunn J Chem Soc 603 1953, resolution: Dean et al. J Chem Soc 1250 1953, synthesis: Barton et al. J Chem Soc 538 1956, Beilstein 18/5 V 586.]

USNIC ACID(125-46-2)Related Product Information

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