USNIC ACID

USNIC ACID Basic information
Product Name:USNIC ACID
Synonyms:(+-)-uanicacid;2,6-diacetyl-1,;2,6-diacetyl-1,2,3,9b-tetrahydro-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione;2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2h,9bh)-dibenzofurandione;Usnic acid, usinic acid;10 GM and 25 GM;Carbonusninic acid;2,6-diacetyl-7,9-dihydroxy-8,9b-diMethyldibenzo[b,d]furan-1,3(2H,9bH)-dione
CAS:125-46-2
MF:C18H16O7
MW:344.32
EINECS:204-740-7
Product Categories:Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Miscellaneous Natural Products;231-456-0
Mol File:125-46-2.mol
USNIC ACID Structure
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
pKa4.00±0.40(Predicted)
Merck 9893
LogP2.880
CAS DataBase Reference125-46-2(CAS DataBase Reference)
EPA Substance Registry SystemUsnic 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 Data125-46-2(Hazardous Substances Data)
ToxicityLD50 i.v. in mice: 25 mg/kg (Gottlieb, Shaw)
MSDS Information
USNIC ACID Usage And Synthesis
Chemical PropertiesCrystalline, yellow solid. Insoluble in water; slightly soluble in alcohol and ether.
Usesantibacterial
UsesUsnic acid is an enzyme inhibiting antitumor agent.
UsesUsnic 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.
DefinitionChEBI: 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 allergensUsnic 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 MethodsThis 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 Preparation Products And Raw materials
3-METHOXY-2-CYCLOHEXEN-1-ONE 3-Methylphenethyl alcohol 3-(3,5-DIMETHYLPHENYL)-1-PROPENE 3-PHENYL-1-PENTENE 2,4-DIHYDROXY-1,3,5-TRIMETHYLBENZENE (2-METHOXYPHENYL)ACETALDEHYDE LABOTEST-BB LT00452089 2-tert-Butyl-6-methylphenol 3-TERT-BUTYL-2-HYDROXYBENZALDEHYDE 2-(1,1-DIMETHYLPROPYL)PHENOL 3-METHYL-1-PHENYL-2-BUTANONE 5-TERT-BUTYL-2-HYDROXY-BENZALDEHYDE 3-METHYLPHENYLACETONE 2',4'-DIHYDROXY-3'-PROPYLACETOPHENONE CHEMBRDG-BB 4016822 1-(3-ALLYL-2,6-DIHYDROXYPHENYL)ETHAN-1-ONE 1-(2,4-DIHYDROXY-5-PROPYLPHENYL)ETHAN-1-ONE 3'-TERT-BUTYLACETOPHENONE

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