Atranorin

Base Information

• Chemical Name: Atranorin
• CAS No.: 479-20-9
• Molecular Formula: C19H18 O8
• Molecular Weight: 374.347
• European Community (EC) Number: 207-527-7
• NSC Number: 685591,249980,87512
• UNII: 450U2VJ2VG
• DSSTox Substance ID: DTXSID10197319
• Nikkaji Number: J12.600D
• Wikipedia: Atranorin
• Wikidata: Q31749378
• Metabolomics Workbench ID: 113666
• ChEMBL ID: CHEMBL173395
• Mol file: 479-20-9.mol

Synonyms:atranorin;atranorin monopotassium

Chemical Property of Atranorin

Chemical Property:

• Vapor Pressure: 4.34E-12mmHg at 25°C
• Melting Point: 156-158°C
• Boiling Point: 535.7°C at 760 mmHg
• Flash Point: 189.3°C
• PSA: 130.36000
• Density: 1.404g/cm³
• LogP: 2.54690
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 374.10016753
• Heavy Atom Count: 27
• Complexity: 564

Purity/Quality:

99%, ^*data from raw suppliers

Atranorin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison by skin contact. A skin irritant.
• Hazard Codes: A poison by skin contact. A skin irritant.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)OC)O)C)O)C=O)O
• 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 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.

Technology Process of Atranorin

There total 1 articles about Atranorin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ atranorin (479-20-9)

Guidance literature:

Haematominsaeure (IX), 2-Methyl-6-methoxycarbonyl-orcin;

Reference yield: 89.0%

atranorin (479-20-9) + 4-methylphenoxyacetyl hydrazide (36304-39-9) → C28H28N2O9

Guidance literature:

With acetic acid; In ethanol; at 50 ℃; for 2h;

DOI:10.1016/j.bmcl.2020.127359

Reference yield: 86.6%

m-tolyloxy-acetic acid hydrazide (36304-38-8) + atranorin (479-20-9) → C28H28N2O9

Guidance literature:

With acetic acid; In ethanol; at 50 ℃; for 2h;

DOI:10.1016/j.bmcl.2020.127359

Downstream raw materials:

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

ethyl hematommate

atranol

methyl haematommate