Introduction：Basic information about ATRANORIN CAS 479-20-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
ATRANORIN Basic information
| Product Name: | ATRANORIN |
| Synonyms: | PARMELIN;USNARIN;ATRANORIN;3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate;3-Formyl-2,4-dihydroxy-6-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester;NSC-685591;ATRANORIN(P);Atrarin |
| CAS: | 479-20-9 |
| MF: | C19H18O8 |
| MW: | 374.34 |
| EINECS: | 207-527-7 |
| Product Categories: | |
| Mol File: | 479-20-9.mol |
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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 |
| 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) |
Safety Information
| WGK Germany | WGK 3 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Skin Sens. 1 |
| 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 skincontact. A skin irritant. When heated todecomposition it emits acrid smoke andirritating 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 |
ATRANORIN Preparation Products And Raw materials
| Preparation Products | 2,6-DIHYDROXY-4-METHYLBENZALDEHYDE |
