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)

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

• Language:English Provider:7-Isopropyl-1,4-dimethylazulene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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(489-84-9)Related Product Information

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