ATRANORIN Chemical Properties

Melting point:

156-158°C

storage temp. 

Store at -20°C

solubility 

Chloroform: soluble,DMSO: soluble

form 

A crystalline solid

color 

White to off-white

LogP

6.140 (est)

Safety Information

Toxicity

skn-gpg 5% CODEDG 11,168,1984

ATRANORIN Usage And Synthesis

Description

Atranorin is a depside lichen metabolite that has been found in S. alpinum and has diverse biological activities. It is active against the bacteria B. cereus, B. subtilis, S. aureus, S. faecalis, P. vulgaris, L. monocytogenes, and A. hydrophila (MICs = 1.67, 0.38, 26.7, 13.4, 3.34, 9.83, and 1.67 mM, respectively), the fungi C. albicans and C. glabrata (MIC = 26.7 mM for both), as well as the mycobacterium M. aurum (MIC = 250 μg/ml). Atranorin is cytotoxic to A270, HL-60, and Jurkat cancer cells (IC₅₀s = 197.9, 93.5, and 181.6 μM, respectively) but not HeLa, MCF-7, SK-BR-3, or HT-29 cancer cells (IC₅₀s = >200 μM). It inhibits acetic acid-induced writhing in mice when administered orally at doses of 200 and 400 mg/kg. Atranorin (200 and 400 mg/kg, p.o.) also reduces paw licking and biting in the second, but not first, phase of the formalin test when administered 30 minutes prior to formalin in mice.

Uses

antinociceptive, antiinflammatory, antibacterial

Uses

Component in extracts of oak moss used as fragrance. Atranorin is a derivative compound of Chloratranorin (C364120), which are metabolites of Evernia prunastri and functions as antioxidant, antimicrobial and potential anticancer agents.

Definition

ChEBI: Atranorin is a carbonyl compound.

Hazard

A poison by skin contact. A skin irritant.

Safety Profile

A poison by skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating vapors.

References

[1] KRISTI?N INGóLFSDóTTIR . Antimycobacterial activity of lichen metabolites in vitro[J]. European Journal of Pharmaceutical Sciences, 1998, 6 2: Pages 141-144. DOI: 10.1016/s0928-0987(97)00078-x
[2] MERAL YILMAZ. The antimicrobial activity of extracts of the lichen Cladonia foliacea and its (-)-usnic acid, atranorin, and fumarprotocetraric acid constituents.[J]. Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences, 2004, 59 3-4: 249-254. DOI: 10.1515/znc-2004-3-423
[3] M. BA?KOROVá . Variable responses of different human cancer cells to the lichen compounds parietin, atranorin, usnic acid and gyrophoric acid[J]. Toxicology in Vitro, 2011, 25 1: Pages 37-44. DOI: 10.1016/j.tiv.2010.09.004
[4] MARCéLIA GARCEZ DóRIA MELO. Purification, physicochemical properties, thermal analysis and antinociceptive effect of atranorin extracted from Cladina kalbii.[J]. Biological & pharmaceutical bulletin, 2008, 31 10: 1977-1980. DOI: 10.1248/bpb.31.1977

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