125-46-2

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;3(2H,9bH)-Dibenzofurandione,2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1;9bh)-dibenzofurandione,2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-3(2h;usninsaeure;usno
• CAS NO: 125-46-2
• Molecular Formula: C18H16O7
• Molecular Weight: 344.32
• EINECS: 231-456-0
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;231-456-0
• Mol File: 125-46-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 200°C
• Boiling Point: 399.43°C (rough estimate)
• Flash Point: 219.1 °C
• Appearance: /
• Density: 1.2869 (rough estimate)
• Vapor Pressure: 3E-15mmHg at 25°C
• Refractive Index: 495 ° (C=0.7, CHCl3)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.00±0.40(Predicted)
• Merck: 9893
• CAS DataBase Reference: USNIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: USNIC ACID(125-46-2)
• EPA Substance Registry System: USNIC ACID(125-46-2)

Safety Data

• Hazard Codes: T,N
• Statements: 25-50/53
• Safety Statements: 22-24/25-61-60-45
• RTECS: HP5270000
• Hazardous Substances Data: 125-46-2(Hazardous Substances Data)

Usage

Chemical Properties

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

Uses

Different sources of media describe the Uses of 125-46-2 differently. You can refer to the following data:
1. Usnic acid is an enzyme inhibiting antitumor agent.
2. antibacterial
3. 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.]

InChI:InChI=1/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/h5,21-23H,1-4H3/t18-/m0/s1

Downstream Products

• 62495-85-6 8-acetyl-5,7-dihydroxy-3,4a,6-trimethyl-1-phenyl-1,4a-dihydro-4H-benzofuro[3,2-f]indazol-4-one 

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Thymol and usnic acid as the important secondary metabolites of respectively Artemisia haussknechtii and Protoparmeliopsis muralis were used for reduction and stabilizing of AgNO3 and CuSO4 in metal nanoparticles (MNPs) biosynthesis process. Antibacterial effects of prepared Ag-thymol (ATNPs), A...detailed

USNIC ACID (cas 125-46-2) reactive metabolites formation in human, rat, and mice microsomes. Implication for hepatotoxicity09/26/2019

Usnic acid is a lichen compound which is extensively studied due to its cytotoxic, antiproliferative, antimicrobial, antiviral, antiprotozoal, and anti-inflammatory activities. Despite a broad spectrum of biological properties, usnic acid is a hepatotoxic agent, thus its potential use as a drug ...detailed

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Because of the increased incidence of infections caused by resistant pathogens, due to the intensive use of antibiotics, there is an urgent need to develop new therapeutic strategies against bacteria, possibly based on non conventional drugs. (+)-Usnic acid is a natural compound that exerts a po...detailed