ChemicalBook > Product Catalog > API > Synthetic Anti-infective Drugs > Antiseptics & Disinfectants Drugs > Guaiazulene
Guaiazulene Chemical Properties
- Melting point:27-29 °C (lit.)
- Boiling point:153 °C/7 mmHg (lit.)
- Density 0.976 g/mL at 25 °C (lit.)
- refractive index 1.3166 (estimate)
- Flash point:>230 °F
- storage temp. Sealed in dry,2-8°C
- form Low Melting Crystalline Solid
- color Dark blue
- Water Solubility Soluble in alcohol, water, 0.1115 mg/L @ 25°C (est).
- Merck 14,4554
- BRN 1365001
- CAS DataBase Reference489-84-9(CAS DataBase Reference)
- NIST Chemistry ReferenceAzulene, 1,4-dimethyl-7-(1-methylethyl)-(489-84-9)
- EPA Substance Registry SystemAzulene, 1,4-dimethyl-7-(1-methylethyl)- (489-84-9)
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
- UsesGuaiazulene 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
Se-Guaiazulene ETHYL GUAIAZULENE SULFONATE 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID Guaiazulene-2-sulphonate GUAIAZULENE 99% ISOPROPYL LAURATE RARECHEM AL BE 1110 RARECHEM AL BI 1110 5-ISOPROPYL-3,8-DIMETHYLAZULENE-1-CARBALDEHYDE HNS 32 RARECHEM AL BF 1110 RARECHEM AL BD 1110 Guaiazulene GUM GUAIAC Dimethyl sebacate Dacthal ISOPROPYLTRICHLOROSILANE Isoproterenol
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