Guaiazulene Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

Guaiazulene Chemical Properties,Usage,Production

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.]