Guaiazulene
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
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.]
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