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Arzanol

AG-CN2-0500-M001 1 mg INQ
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Product Data
Synonyms Homoarenol; 3-[[3-Acetyl-2,4,6-trihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one
Properties
Formula C22H26O7
MW 402.4
CAS 32274-52-5
Source/Host Isolated from Helichrysum italicum.
Purity ≥98% (NMR)
Appearance Off-white solid to pale yellow solid.
Solubility Soluble in DMSO, dichloromethane, acetone or 100% ethanol. Poorly soluble in water.
Identity Determined by 1H-NMR.
InChi Key ZOIAPLVBZQQHCG-UHFFFAOYSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry. Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
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Product Description

  • Anti-inflammatory compound. Potent dual inhibitor of pro-inflammatory transcription factors and inflammatory enzymes.
  • Inhibitor of NFκB activation.
  • Potent inhibitor of inducible microsomal prostaglandin E2 synthase-1 (mPGES-1), the terminal synthase responsible for the synthesis of the pro-tumorigenic prostaglandin E2 (PGE2).
  • Antioxidant. 5-Lipoxygenase (5-LO) inhibitor.
  • Antibacterial compound.
  • HIV-1 replication inhibitor.

Product References

  1. Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum: G. Appendino, et al.; J. Nat. Prod. 70, 608 (2007)
  2. Evaluation of the antioxidant and cytotoxic activity of arzanol, a prenylated alpha-pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp. microphyllum: A. Rosa, et al.; Chem. Biol. Interact. 165, 117 (2007)
  3. Arzanol, a prenylated heterodimeric phloroglucinyl pyrone, inhibits eicosanoid biosynthesis and exhibits anti-inflammatory efficacy in vivo: J. Bauer, et al.; Biochem. Pharmacol. 81, 259 (2011)
  4. Protective role of arzanol against lipid peroxidation in biological systems: A. Rosa, et al.; Chem. Phys. Lipids 164, 24 (2011)
  5. A Multicomponent Carba-Betti Strategy to Alkylidene Heterodimers - Total Synthesis and Structure - Activity Relationships of Arzanol: A. Minassi, et al.; Eur. J. Org. Chem. 772 (2012)
  6. Arzanol, a potent mPGES-1 inhibitor: Novel anti-inflammatory agent: P. S. Kothavade, et al.; Sci. World J. 2013, 986429 (2013) (Review)
  7. Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum: O. Taglialatela-Scafati, et al.; J. Nat. Prod. 76, 346 (2013)
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