| Identification | Back Directory | [Name]
ATRANORIN | [CAS]
479-20-9 | [Synonyms]
USNARIN
Atrarin
PARMELIN
ATRANORIN
NSC-685591
ATRANORIN(P)
3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate
Benzoic acid,3-formyl-2,4-dihydroxy-6-methyl-,3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
3-Formyl-2,4-dihydroxy-6-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester | [EINECS(EC#)]
207-527-7 | [Molecular Formula]
C19H18O8 | [MDL Number]
MFCD00016597 | [MOL File]
479-20-9.mol | [Molecular Weight]
374.34 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [Uses]
antinociceptive, antiinflammatory, antibacterial | [Hazard]
A poison by skin contact. A skin irritant.
| [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. | [Definition]
ChEBI: Atranorin is a carbonyl compound. |
| Safety Data | Back Directory | [Safety Profile]
A poison by skin
contact. A skin irritant. When heated to
decomposition it emits acrid smoke and
irritating vapors. | [Toxicity]
skn-gpg 5% CODEDG 11,168,1984 |
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