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
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) |
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
Abamectin manufacturer
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