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Guaiazulene

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CAS:489-84-9
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Guaiazulene manufacturers

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  • 2024-10-31
  • CAS:489-84-9
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Guaiazulene Basic information
Product Name:Guaiazulene
Synonyms:1,4-dimethyl-7-(1-methylethyl)-azulen;1,4-Dimethyl-7-(1-methylethyl)azulene;1,4-dimethyl-7-(1-methylethyl)-Azulene;1,4-dimethyl-7-isopropyl-azulen;3,8-Dimethyl-5-(2-propyl)azulene;AZ-8;AZ-8 beris;Azulen-Beris
CAS:489-84-9
MF:C15H18
MW:198.3
EINECS:207-701-2
Product Categories:Arenes;Building Blocks;Chemical Synthesis;Organic Building Blocks;Azulenes;Biochemistry;Terpenes;Terpenes (Others);Tropolones & Azulenes
Mol File:489-84-9.mol
Guaiazulene Structure
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)
Fp >230 °F
storage temp. Sealed in dry,2-8°C
solubility Chloroform (Slightly), Methanol (Sparingly)
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
LogP5.590 (est)
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)
Safety Information
Hazard Codes Xn
Risk Statements 22-20/21/22
Safety Statements 36/37/39-26-22-36
WGK Germany 3
RTECS CO4790000
TSCA Yes
HS Code 2902190000
MSDS Information
ProviderLanguage
7-Isopropyl-1,4-dimethylazulene English
SigmaAldrich English
ACROS English
ALFA English
Guaiazulene Usage And Synthesis
Chemical PropertiesDARK BLUE LOW MELTING CRYSTALLINE SOLID
OriginatorAZ 8,Millet Roux
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.

Usesantioxidant, inhibits lipid peroxidation inhibitor, antiinflammatory, hepatoprotectant; LD50(rat) 1550 mg/kg po
DefinitionChEBI: Guaiazulene is a sesquiterpene. It derives from a hydride of a guaiane.
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
General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
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.]
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