Guaiazulene

Base Information

• Chemical Name: Guaiazulene
• CAS No.: 489-84-9
• Deprecated CAS: 12040-47-0
• Molecular Formula: C15H18
• Molecular Weight: 198.308
• Hs Code.: 2902190000
• European Community (EC) Number: 207-701-2
• NSC Number: 4714
• UNII: 2OZ1K9JKQC
• DSSTox Substance ID: DTXSID7045996
• Nikkaji Number: J11.635A
• Wikipedia: Guaiazulene
• Wikidata: Q3026266
• Metabolomics Workbench ID: 28332
• ChEMBL ID: CHEMBL1408759
• Mol file: 489-84-9.mol

Synonyms:Azulene,7-isopropyl-1,4-dimethyl- (8CI); 1,4-Dimethyl-7-(1-methylethyl)Azulene;1,4-Dimethyl-7-isopropylazulene; 3,8-Dimethyl-5-(2-propyl)azulene;7-Isopropyl-1,4-dimethylazulene; AZ 8; AZ 8 Beris; Azulen-Beris; Azulon;Azunol; Cuteazul; Eucazulen; Guaiazulene; Guaiazulene blue; Kessazulen; NSC4714; Purazulen; S-Guaiazulene; Silazulon; Uroazulen; Vaumigan; Vetivazulen

Chemical Property of Guaiazulene

Chemical Property:

• Appearance/Colour: dark blue semi-solid
• Vapor Pressure: 0.00148mmHg at 25°C
• Melting Point: 28 - 30 C
• Refractive Index: 1.572
• Boiling Point: 153 °C7 mm Hg(lit.)
• Flash Point: 113 ºC
• PSA: 0.00000
• Density: 0.976
• LogP: 4.53160
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Sparingly)
• Water Solubility.: Soluble in alcohol, water, 0.1115 mg/L @ 25°C (est).
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 198.140850574
• Heavy Atom Count: 15
• Complexity: 206

Purity/Quality:

99.9% by G.C ^*data from raw suppliers

Guaiazulene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-20/21/22
• Safety Statements: 36/37/39-26-22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC(=C2C=C(C=C1)C(C)C)C
• Recent ClinicalTrials: Glucocorticosteroid Therapy on Drug-induced Liver Injury: a Prospective Non-randomized Concurrent Control Trial
• Recent NIPH Clinical Trials: Randomized controlled study comparing 1% of Dermacrin A ointmentwith 0.033% of Guaiazulene ointment for patients with perianal delmatitis after total colectomy
• Uses: antioxidant, inhibits lipid peroxidation inhibitor, antiinflammatory, hepatoprotectant; LD50(rat) 1550 mg/kg po 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.
• Therapeutic Function: Antiinflammatory

Technology Process of Guaiazulene

There total 73 articles about Guaiazulene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene (1203707-11-2) + azulene (275-51-4) → 7-isopropyl-1,4-dimethyl-azulene (489-84-9) + 2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene (1314045-03-8)

Guidance literature:

With hydrogenchloride; In methanol; water; acetonitrile; at 60 ℃; for 3h;

DOI:10.1016/j.tet.2011.05.038

Reference yield: 94.0%

1-chloro-7-isopropyl-4-methyl-azulene (867380-19-6) + dihydroxy-methyl-borane (13061-96-6) → 7-isopropyl-1,4-dimethyl-azulene (489-84-9)

Guidance literature:

With palladium diacetate; potassium phosphate; In toluene; at 100 ℃; for 24h;

DOI:10.1002/anie.200501276

Reference yield: 93.0%

azulene (275-51-4) + 1,1-bis[4-(methoxy)phenyl]-2-(3-guaiazulenyl)ethylene (741737-71-3) → 7-isopropyl-1,4-dimethyl-azulene (489-84-9) + 1,3-bis[2,2-bis(4-methoxyphenyl)ethenyl]azulene (1314045-02-7) + 2-(azulen-1-yl)-1,1-bis(4-methoxyphenyl)ethylene

Guidance literature:

With hydrogenchloride; In methanol; water; acetonitrile; at 60 ℃; for 3h;

DOI:10.1016/j.tet.2011.05.038

upstream raw materials:

pyridine

p-toluenesulfonyl chloride

6-isopropyl-4,9-dimethyl-octahydro-cyclohepta[b]pyran-2-one

kessyl glycol

Downstream raw materials:

(5-isopropyl-3,8-dimethylazulen-1-yl)(phenyl)methanone

5-isopropyl-3,8-dimethylazulene-1-carbaldehyde

3-(p-Tolylazo)guaiazulen

lactaroazulene

Refernces

• 1、 Yoshioka et al.. "". . p. 923. Retrieved 1970.
• 2、 Melville. "". . p. 2462,2464, 3288, 3291. Retrieved 1933.
• 3、 Fattorusso et al.. "". . p. 3911. Retrieved 1974.
• 4、 House et al.. "". . p. 639. Retrieved 1960.
• 5、 Saidkhodzhaev et al.. "". . . Retrieved 1977.
• 6、 Jacob,T.M. et al.. "". . p. 2821 - 2827. Retrieved 1964.
• 7、 Takekuma, Shin-Ichi,Kaibara, Masamichi,Minematsu, Toshie,Takekuma, Hideko. "Reaction of azulene with 1,2-bis[4-(dimethylamino)phenyl]-1,2-ethanediol in a mixed solvent of methanol and acetonitrile in the presence of hydrochloric acid: A facile one-pot synthesis and properties of new triarylethylenes possessing an azulen-1-yl group". experimental part. p. 4780 - 4792. Retrieved 2011/08/03.
• 8、 Moreno-Dorado, F. Javier,Lamers, Yvonne M. A. W.,Mironov, Grigore,Wijnberg, Joannes B. P. A.,De Groot, Aede. "Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides". . p. 7743 - 7750. Retrieved 2007/10/03.