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MedKoo Cat#: 565254 | Name: Arzanol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Arzanol is a positive modulator of brain glycogen phosphorylase.

Chemical Structure

Arzanol
CAS#32274-52-5

Theoretical Analysis

MedKoo Cat#: 565254

Name: Arzanol

CAS#: 32274-52-5

Chemical Formula: C22H26O7

Exact Mass: 402.1679

Molecular Weight: 402.44

Elemental Analysis: C, 65.66; H, 6.51; O, 27.83

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Related CAS #
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Synonym
Arzanol
IUPAC/Chemical Name
3-[[3-Acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methylpyran-2-one
InChi Key
ZOIAPLVBZQQHCG-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H26O7/c1-6-16-11(4)18(24)15(22(28)29-16)9-14-19(25)13(8-7-10(2)3)20(26)17(12(5)23)21(14)27/h7,24-27H,6,8-9H2,1-5H3
SMILES Code
O=C1C(CC2=C(O)C(C/C=C(C)\C)=C(O)C(C(C)=O)=C2O)=C(O)C(C)=C(CC)O1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 402.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Rosa A, Deiana M, Atzeri A, Corona G, Incani A, Melis MP, Appendino G, Dessì MA. Evaluation of the antioxidant and cytotoxic activity of arzanol, a prenylated alpha-pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp.microphyllum. Chem Biol Interact. 2007 Jan 30;165(2):117-26. Epub 2006 Nov 23. PubMed PMID: 17194458. 2: Appendino G, Ottino M, Marquez N, Bianchi F, Giana A, Ballero M, Sterner O, Fiebich BL, Munoz E. Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum. J Nat Prod. 2007 Apr;70(4):608-12. Epub 2007 Feb 22. PubMed PMID: 17315926. 3: Rosa A, Pollastro F, Atzeri A, Appendino G, Melis MP, Deiana M, Incani A, Loru D, Dessì MA. Protective role of arzanol against lipid peroxidation in biological systems. Chem Phys Lipids. 2011 Jan;164(1):24-32. doi: 10.1016/j.chemphyslip.2010.09.009. Epub 2010 Oct 7. PubMed PMID: 20932961. 4: Bauer J, Koeberle A, Dehm F, Pollastro F, Appendino G, Northoff H, Rossi A, Sautebin L, Werz O. Arzanol, a prenylated heterodimeric phloroglucinyl pyrone, inhibits eicosanoid biosynthesis and exhibits anti-inflammatory efficacy in vivo. Biochem Pharmacol. 2011 Jan 15;81(2):259-68. doi: 10.1016/j.bcp.2010.09.025. Epub 2010 Oct 8. PubMed PMID: 20933508. 5: Taglialatela-Scafati O, Pollastro F, Chianese G, Minassi A, Gibbons S, Arunotayanun W, Mabebie B, Ballero M, Appendino G. Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum. J Nat Prod. 2013 Mar 22;76(3):346-53. doi: 10.1021/np3007149. Epub 2012 Dec 24. PubMed PMID: 23265253. 6: Kothavade PS, Nagmoti DM, Bulani VD, Juvekar AR. Arzanol, a potent mPGES-1 inhibitor: novel anti-inflammatory agent. ScientificWorldJournal. 2013 Oct 1;2013:986429. doi: 10.1155/2013/986429. eCollection 2013. Review. PubMed PMID: 24198734; PubMed Central PMCID: PMC3807707. 7: Venditti A, Lattanzi C, Ornano L, Maggi F, Sanna C, Ballero M, Alvino A, Serafini M, Bianco A. A new glucosidic phthalide from Helichrysum microphyllum subsp. tyrrhenicum from La Maddalena Island (Sardinia, Italy). Nat Prod Res. 2016;30(7):789-95. doi: 10.1080/14786419.2015.1067619. Epub 2015 Aug 3. PubMed PMID: 26235805. 8: Rosa A, Atzeri A, Nieddu M, Appendino G. New insights into the antioxidant activity and cytotoxicity of arzanol and effect of methylation on its biological properties. Chem Phys Lipids. 2017 Jun;205:55-64. doi: 10.1016/j.chemphyslip.2017.05.001. Epub 2017 May 3. PubMed PMID: 28476462. 9: Mammino L. Intramolecular Hydrogen Bonding and Conformational Preferences of Arzanol-An Antioxidant Acylphloroglucinol. Molecules. 2017 Aug 3;22(8). pii: E1294. doi: 10.3390/molecules22081294. PubMed PMID: 28771203; PubMed Central PMCID: PMC6152391. 10: Mammino L. Complexes of arzanol with a Cu(2+) ion: a DFT study. J Mol Model. 2017 Sep 12;23(10):276. doi: 10.1007/s00894-017-3443-4. PubMed PMID: 28900733. 11: Del Gaudio F, Pollastro F, Mozzicafreddo M, Riccio R, Minassi A, Monti MC. Chemoproteomic fishing identifies arzanol as a positive modulator of brain glycogen phosphorylase. Chem Commun (Camb). 2018 Nov 13;54(91):12863-12866. doi: 10.1039/c8cc07692h. PubMed PMID: 30375590.