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Guaiazulene

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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
  • Azulenes
  • Biochemistry
  • Chemical Synthesis
  • Organic Building Blocks
  • Terpenes
  • Terpenes (Others)
  • Tropolones & Azulenes
Mol File:
489-84-9.mol
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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
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
LogP
5.590 (est)
CAS DataBase Reference
489-84-9(CAS DataBase Reference)
NIST Chemistry Reference
Azulene, 1,4-dimethyl-7-(1-methylethyl)-(489-84-9)
EPA Substance Registry System
Azulene, 1,4-dimethyl-7-(1-methylethyl)- (489-84-9)
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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

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Guaiazulene Usage And Synthesis

Chemical Properties

DARK BLUE LOW MELTING CRYSTALLINE SOLID

Originator

AZ 8,Millet Roux

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.

Uses

antioxidant, inhibits lipid peroxidation inhibitor, antiinflammatory, hepatoprotectant; LD50(rat) 1550 mg/kg po

Definition

ChEBI: Guaiazulene is a sesquiterpene. It derives from a hydride of a guaiane.

Manufacturing Process

10 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 Function

Antiinflammatory

General Description

This 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 Methods

It 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

Preparation Products

GuaiazuleneSupplier

Xi'an Yutai Pharmaceutical Co., Ltd. Gold
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Zhongxiang Yaowei Biological Technology Co., Ltd. Gold
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Nanjing Bermuda Biotechnology Co., Ltd. Gold
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Wuhan Wiseman Bioengineering Co.,Ltd Gold
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Wuhan haorong Biotechnology Co., Ltd Gold
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13217229939
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