Identification | More | [Name]
Guaiazulene | [CAS]
489-84-9 | [Synonyms]
1,4-DIMETHYL-7-ISOPROPYLAZULENE 7-ISOPROPYL-1,4-DIMETHYLAZULENE AZULON GUAIAZULENE GUAJAZULEN LABOTEST-BB LT00244815 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 Azulene, 1,4-dimethyl-7-isopropyl- Azulene, 7-isopropyl-1,4-dimethyl- Azulol Azunol Cuteazul Eucazulen | [EINECS(EC#)]
207-701-2 | [Molecular Formula]
C15H18 | [MDL Number]
MFCD00003811 | [Molecular Weight]
198.3 | [MOL File]
489-84-9.mol |
Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S22:Do not breathe dust . S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
CO4790000
| [TSCA ]
Yes | [HS Code ]
2902190000 |
Raw materials And Preparation Products | Back Directory | [Raw materials]
Sulfur-->Ethanamine, 2,2'-[[2-[3,8-dimethyl-5-(1-methylethyl)-1-azulenyl]ethenylidene]bis(4,1-phenyleneoxy)]bis[N,N-dimethyl--->Magnesium, iodo(1-methylethyl)- (9CI)-->Azulene, 3-[2,2-bis(4-methoxyphenyl)ethenyl]-1,4-dimethyl-7-(1-methylethyl)--->Azulene-->Methylboronic acid | [Preparation Products]
GUM GUAIAC-->Guaiacwood oil-->[1,4-Dimethyl-7-(1-methylethyl)-2-azulenyl]phenylmethanone |
Hazard Information | Back Directory | [Chemical Properties]
DARK BLUE LOW MELTING CRYSTALLINE SOLID | [Originator]
AZ 8,Millet Roux | [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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