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SBR00002

Arzanol

Name: Arzanol
Brand: SIGMA

from Helichrysum italicum, ≥98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₆O₇

CAS Number:

32274-52-5

Molecular Weight:

402.44

NACRES:

NA.25

PubChem Substance ID:

329824643

UNSPSC Code:

12352200

MDL number:

MFCD28168041

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Properties

biological source

Helichrysum italicum

Quality Segment

200

assay

≥98%

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

OC1=C(CC2=C(O)C(C)=C(CC)OC2=O)C(O)=C(C(C)=O)C(O)=C1CC=C(C)C

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

InChI key

ZOIAPLVBZQQHCG-UHFFFAOYSA-N

Description

General description

Arzanol is a pyrone–phloroglucinol etherodimer. It is a polyphenol compound extracted from the plant Helichrysum italicum which grows in the Mediterranean area.

Application

Arzanol has been used to test its effects as an autophagy modulator on HeLa cells and bladder cancer cells

Biochem/physiol Actions

Arzanol is known for its anti-inflammatory and antimicrobial activities. The anti-inflammatory activity was verified in an in-vivo rat model and was found to suppress the inflammatory response of the carrageenan-induced pleurisy. Moreover it was found to have an anti-HIV-1 activity. Arzanol inhibits COX-2-derived prostaglandin synthase-1 (mPGES-1) Inhibitor in-vitro, in human stimulated monocytes.
Arzanol inhibits the activation of inflammatory transcription factor nuclear factor-KB (NF-KB), human immunodeficiency virus (HIV) replication in T cells, releases of interleukin (IL)-1β, IL-6, IL-8, and tumor necrosis factor (TNF)-α and biosynthesis of prostaglandin E2 (PGE2) by potentially inhibiting the mPGES-1 enzyme. It also possesses antioxidant and cytotoxic activity.

Arzanol is a polyphenol compound extracted from the plant Helichrysum italicum which grows in the Mediterranean area. Arzanol is known for its anti-inflammatory and antimicrobial activities. The anti-inflammatory activity was verified in an in-vivo rat model and was found to suppress the inflammatory response of the carrageenan-induced pleurisy.Moreover it was found to have an anti-HIV-1 activity. Arzanol inhibits COX-2-derived prostaglandin synthase-1 (mPGES-1) Inhibitor in-vitro, in human stimulated monocytes.
Arzanol inhibits the activation of inflammatory transcription factor NFκB, HIV replication in T cells, releases of IL-1β, IL-6, IL-8, and TNF-α,and biosynthesis of PGE2 by potentially inhibiting the mPGES-1 enzyme.

Demonstrates anti-inflammatory and antimicrobial activity., Inhibits COX-2-derived prostaglandin synthase- (mPGES)-1 Inhibitor in-vitro, in human stimulated monocytes.

Preparation Note

Soluble in dimethyl sulfoxide (DMSO) at 1 mg/mL; poorly soluble in water

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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