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HomeProduct name listGuaiazulene

Guaiazulene

Synonym(s):1,4-Dimethyl-7-isopropylazulene

  • CAS NO.:489-84-9
  • Empirical Formula: C15H18
  • Molecular Weight: 198.3
  • MDL number: MFCD00003811
  • EINECS: 207-701-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-20 11:41:24
Guaiazulene Structural

What is Guaiazulene?

Chemical properties

DARK BLUE LOW MELTING CRYSTALLINE SOLID

Originator

AZ 8,Millet Roux

The Uses of Guaiazulene

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.

The Uses of Guaiazulene

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

What are the applications of Application

Guaiazulene is A derivative of azulene

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.]

Properties of Guaiazulene

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
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 for Guaiazulene

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P501:Dispose of contents/container to..…

Computed Descriptors for Guaiazulene

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