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Guaiazulene

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Guaiazulene Basic information
Guaiazulene Chemical Properties
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MSDS
Guaiazulene Usage And Synthesis
  • Chemical PropertiesDARK BLUE LOW MELTING CRYSTALLINE SOLID
  • OriginatorAZ 8,Millet Roux
  • Usesantioxidant, inhibits lipid peroxidation inhibitor, antiinflammatory, hepatoprotectant; LD50(rat) 1550 mg/kg po
  • Uses
    Guaiazulene can be used as a starting material for the synthesis of:
    • Azulene-based dye molecules such as 3-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanoacrylic acid and 5-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanopenta-2,4-dienoic acid.
    • Stilbazulenyl nitrone, a second-generation azulenyl nitrone which can be used as a chain-breaking antioxidant.
    • Bis-azulenyl based near-infrared fluorescence quencher.

  • Manufacturing Process10 kg a gum of Guacum officinale was heated with 3-4 kg of sulfur to 130°C. The heating was slowly continued for 220°C under the nitrogen. The formed water steam was removed with the nitrogen current. The temperature should be higher 100°C in order to the water didnt fall into reaction mixture. H2S was obtained simultaneously the dehydrogenation and removed with water steam. Hydrogen sulfide was connected in an alkaline trap.
    When a H2S discharge stopped, the temperature was decreased to 120°C and the reaction mixture was distilled in vacuum 1-20 mm. The distillate had deep blue color and contained 6-7 kg oil with 20% of 7-isopropyl-1,4- dimethylazulene. It was dissolved in the 5-10 volumes of light petroleum, shook with sodium hydroxide for removing the sulfur containing substaneces, washed to neutral. Then petrolem layer was mixed with 10-15 L 62% H2SO4 for removing the by-products, the petroleum layer lost the blue color and the desired substance was in sulphuric acid layer. The last one was shook with ice and NaOH. As a result about 7% NaSO4 solution in sulfuric acid was obtained. It was diluted and azulene gave an emulsion, which was extracted with 10 L of petrolem and distilled. The 7-isopropyl-1,4-dimethylazulene is distilled at 167°-168°C/12 mm. Yield 10-15%.
  • Therapeutic FunctionAntiinflammatory
  • Purification MethodsIt forms blue-violet plates from EtOH. Also redistil it in vacuo until distillate solidifies. UV has max at 284nm (log 4.6, heptane). The picrate has m 122o(EtOH). [Beilstein 5 III 1677, 5 IV 1751.]
Guaiazulene Preparation Products And Raw materials
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