Dehydrozingerone

Sinonimi: 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one, Dehydrozingerone, DHZ, (E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one, Vanillylideneacetone, 4-Hydroxy-3-methoxybenzylideneacetone

Dehydrozingerone is a phenolic ketone that occurs naturally in ginger (Zingiber officinale) and serves as the immediate biosynthetic precursor to zingerone, the compound responsible for much of ginger’s characteristic pungency and biological activity. While zingerone itself is formed through the hydrogenation of dehydrozingerone during ginger processing, the unsaturated parent compound has attracted independent interest for its distinct chemical reactivity and enhanced biological effects. It typically appears as an off-white to pale yellow crystalline solid with a mild, sweet-spicy aroma reminiscent of ginger.

Chemically, dehydrozingerone belongs to the curcuminoid family and shares the feruloyl moiety with curcumin, but its smaller molecular size and lack of a second aromatic ring give it superior solubility and membrane permeability. This structural simplicity makes it an attractive scaffold for synthetic modifications and a valuable reference compound in studies of Michael acceptors, antioxidant mechanisms, and anti-inflammatory pathways. Its α,β-unsaturated carbonyl system is a key feature that enables both its bioactivity and its utility as a chemical intermediate.

In the pharmaceutical and nutraceutical industries, dehydrozingerone is used as a reference standard, a synthetic intermediate for more complex molecules, and an active ingredient in formulations targeting oxidative stress, inflammation, and metabolic health. It is also employed in flavor and fragrance applications where a stable, crystalline ginger-like note is desired. The compound is generally regarded as safe for use in food and cosmetic applications when produced under appropriate quality systems.

Funzione

• Antioxidant activity: Scavenges free radicals and upregulates endogenous antioxidant enzymes, protecting cells from oxidative damage.
• Anti-inflammatory effects: Inhibits NF-κB and COX-2 pathways, reducing pro-inflammatory cytokine production.
• Antimicrobial properties: Demonstrates activity against a range of bacteria and fungi, including foodborne pathogens.
• Metabolic support: May improve insulin sensitivity and lipid profiles in preclinical models.
• Neuroprotective potential: Exhibits protective effects against oxidative stress-induced neuronal damage.
• Flavor and fragrance: Provides a stable ginger-like aroma and taste for food and cosmetic products.

Fonte e standardizzazione

• Fonte: Synthetic or isolated from natural sources (ginger)
• Produzione: Chemical synthesis via aldol condensation of vanillin and acetone, followed by purification
• Standardizzazione: ≥98.0% (HPLC)
• Moduli: Off-white to pale yellow crystalline powder
• Applicazioni: Pharmaceutical intermediates, nutraceuticals, cosmetics, flavor and fragrance, research

Caratteristiche tecniche

Documentazione e forniture

• Capacità mensile: 5 tonnellate metriche
• Tempi di consegna: 3-5 business days (stock items)
• Documentazione: COA, MSDS, TDS, and additional regulatory support available upon request
• Confezionamento: 25 kg fiber drum with double PE liner; custom packaging options available

Richiesta di preventivo

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