Dehydrozingerone

Dehydrozingerone

Tên sản phẩm Dehydrozingerone
Số CAS 1080-12-2
Các tên gọi khác 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one; DHZ; Dehydrozingerone; (E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one
Công thức phân tử C11H12O3
Trọng lượng phân tử 192.21 g/mol
Hình thức Off-white to pale yellow crystalline powder
Phương pháp phân tích (HPLC) ≥98,01 TP3T
Điểm nóng chảy 110-113 °C
Mất mát khi sấy khô ≤0.5%
Hàm lượng tro sau khi đốt ≤0.1%
Kim loại nặng ≤10 ppm
Độ hòa tan Soluble in ethanol, DMSO, ethyl acetate; slightly soluble in water
Gói 25 kg fiber drum with double PE liner

Dehydrozingerone Structure

Từ đồng nghĩa: 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.

Chức năng

  • 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.

Nguồn gốc và tiêu chuẩn hóa

  • Nguồn: Synthetic or isolated from natural sources (ginger)
  • Production: Chemical synthesis via aldol condensation of vanillin and acetone, followed by purification
  • Tiêu chuẩn hóa: ≥98.0% (HPLC)
  • Forms: Off-white to pale yellow crystalline powder
  • Ứng dụng: Pharmaceutical intermediates, nutraceuticals, cosmetics, flavor and fragrance, research

Thông số kỹ thuật

Tham số Thông số kỹ thuật
Phương pháp phân tích (HPLC) ≥98,01 TP3T
Xác định IR, NMR, or HPLC retention time conforms to standard
Mất mát khi sấy khô ≤0.5%
Hàm lượng tro sau khi đốt ≤0.1%
Kim loại nặng ≤10 ppm
Giới hạn vi sinh vật Total aerobic count ≤1000 CFU/g; Yeast & Mold ≤100 CFU/g; E. coli absent

Documentation & Supply

  • Công suất hàng tháng: 5 metric tons
  • Thời gian thực hiện: 3-5 business days (stock items)
  • Tài liệu hướng dẫn: COA, MSDS, TDS, and additional regulatory support available upon request
  • Bao bì: 25 kg fiber drum with double PE liner; custom packaging options available

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