| 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 | [InChI]
1S/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3 | [InChIKey]
YLOYKYXNDHOHHT-UHFFFAOYSA-N | [SMILES]
COC(=O)c1c(C)cc(OC(=O)c2c(C)cc(O)c(C=O)c2O)c(C)c1O | [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. | [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 |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Skin Sens. 1 | [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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