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ChemicalBook--->CAS DataBase List--->489-84-9

489-84-9

489-84-9 Structure

489-84-9 Structure
IdentificationMore
[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
Chemical PropertiesBack Directory
[Appearance]

DARK BLUE LOW MELTING CRYSTALLINE SOLID
[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)
[Fp ]

>230 °F
[storage temp. ]

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]

489-84-9(EPA Substance)
Safety DataBack 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 ProductsBack 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
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

7-Isopropyl-1,4-dimethylazulene(489-84-9).msds
Hazard InformationBack 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.]
Spectrum DetailBack Directory
[Spectrum Detail]

Guaiazulene(489-84-9)MS
Guaiazulene(489-84-9)1HNMR
Guaiazulene(489-84-9)13CNMR
Guaiazulene(489-84-9)IR1
Guaiazulene(489-84-9)IR2
Guaiazulene(489-84-9)Raman
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

Guaiazulene, 98+%(489-84-9)
[Sigma Aldrich]

489-84-9(sigmaaldrich)
[TCI AMERICA]

Guaiazulene,>98.0%(GC)(489-84-9)
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