1,4-dimethyl-7-(propan-2-yl)azulene

• ChemBase ID: 85834
• Molecular Formular: C15H18
• Molecular Mass: 198.30342
• Monoisotopic Mass: 198.14085058
• SMILES: Cc1c2c(c(ccc(c2)C(C)C)C)cc1
• Canonical SMILES: CC(c1ccc(c2c(c1)c(C)cc2)C)C
• InChI: InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3
• InChIKey: FWKQNCXZGNBPFD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-dimethyl-7-(propan-2-yl)azulene
• IUPAC Traditional name: 1,4-dimethyl-7-(propan-2-yl)azulene; guaiazulene
• Synonyms: S - Guaiazulene; Kessazulene; Azulon; Eucazulene; Azunol; 1,4-Dimethyl-7-isopropylazulene; Guaiazulene; 7-isopropyl-1,4-dimethylazulene; GUAIAZULENE; Guaiazulene; 1,4-Dimethyl-7-(prop-2-yl)azulene; 1,4-Dimethyl-7-isopropylazulene; 1,4-二甲基-7-异丙基薁; 愈创奥

Database IDs

• CAS Number: 489-84-9
• EC Number: 207-701-2
• MDL Number: MFCD00003811
• Beilstein Number: 1365001
• Merck Index: 144554
• PubChem SID: 162072950; 24895038
• PubChem CID: 3515
• CHEBI ID: 5550
• Chemspider ID: 3395
• KEGG ID: D01037
• Unique Ingredient Identifier: 2OZ1K9JKQC
• Wikipedia Title: Guaiazulene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.2345743
• LogD (pH = 7.4): 5.2345743
• Log P: 5.2345743
• Molar Refractivity: 66.7814 cm^3
• Polarizability: 27.009663 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 27°C; 27-29 °C(lit.); 31°C; 31-33 °C; 31-33°C
• Boiling Point: 152-154°C/7mm; 153 °C (7 mm Hg); 153 °C/7 mmHg(lit.); 153°C/7mm; 165°C
• Flash Point: >110°C(230°F); 113 °C; 113°C; 235.4 °F
• Density: 0.976; 0.976 g/cm^3; 0.976 g/mL at 25 °C(lit.)

Safety Information

• Storage Warning: Harmful/Irritant/Light Sensitive/Air Sensitive
• RTECS: CO4790000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 36; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301; H302
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Mechanism of Action: Antioxidant; Inhibits lipid peroxidation

Product Information

• Purity: 97%; 98+%; 99%
• Biological Source: Found also in marine red algae and the gorgonian Euplexaura erecta
• Application(s): Also used to treat gastrointestinal disorders; Antiinflammatory agent; Antioxidant; Hepatoprotectant
• Empirical Formula (Hill Notation): C15H18

DETAILS

MP Biomedicals - 05203548

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157281

(1,4-Dimethyl-7-isopropylazulene)

Sigma Aldrich - G11004

Packaging
10, 25 g in glass bottle

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 40B, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 955D, (ir)
• Aldrich Library of FT-IR Spectra: Vapor Phase, 1989, 3, 877B, (ir)
• Plattner, P.A. et al., Helv. Chim. Acta, 1949, 32, 2137; 2452, (synth)
• Sorm, F. et al., Coll. Czech. Chem. Comm., 1951, 16, 168; 626, (isol, synth)
• Caujolle, F. et al., Ann. Pharm. Fr., 1952, 10, 412, (pharmacol)
• Herz, A., Arzneim.-Forsch., 1953, 3, 253, (pharmacol)
• Jacob, T.M. et al., Tetrahedron, 1964, 20, 2821, (uv, synth)
• Llinas, J.R. et al., Can. J. Chem., 1975, 53, 2911, (pmr, cmr)
• Hoffmann, W. et al., Tet. Lett., 1975, 533, (synth)
• Mukherjee, D. et al., J.A.C.S., 1979, 101, 251, (synth)
• Fusetani, N. et al., Experientia, 1981, 37, 680, (isol)
• Li, M.K.W. et al., Tet. Lett., 1984, 25, 587, (derivs)
• Vidal-Ollivier, E. et al., J. Chromatogr., 1989, 463, 227, (hplc)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1688
• Kourounakis, A.P. et al., Arch. Pharm. (Weinheim, Ger.), 1997, 330, 7, (pharmacol)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DSJ800