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G11004

Sigma-Aldrich

Guaiazulene

99%

Synonym(s):

1,4-Dimethyl-7-isopropylazulene

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About This Item

Empirical Formula (Hill Notation):
C15H18
CAS Number:
489-84-9
Molecular Weight:
198.30
Beilstein:
1365001
EC Number:
207-701-2
MDL number:
MFCD00003811
UNSPSC Code:
12352100
PubChem Substance ID:
24895038
NACRES:
NA.22

Quality Level

100

Assay

99%

bp

153 °C/7 mmHg (lit.)

mp

27-29 °C (lit.)

density

0.976 g/mL at 25 °C (lit.)

SMILES string

CC(C)c1ccc(C)c2ccc(C)c2c1

InChI

1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

InChI key

FWKQNCXZGNBPFD-UHFFFAOYSA-N

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Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lei Wang et al.
Mutation research, 530(1-2), 19-26 (2003-10-18)
The photomutagenicity of the popular skin conditioning agents azulene and guaiazulene were tested in Salmonella typhimurium TA98, TA100 and TA102. Following irradiation with UVA and/or visible light, both azulene and guaiazulene exhibited mutagenicity 4-5-fold higher than the spontaneous background mutation.
An Azulene Dimer as a Near-Infrared Quencher.
Pham W, et al.
Angewandte Chemie (International Edition in English), 41(19), 3659-3662 (2002)
Jessica Fiori et al.
Journal of pharmaceutical and biomedical analysis, 47(4-5), 710-715 (2008-04-09)
A liquid chromatographic method with UV detection (HPLC-DAD) and a gas chromatographic method coupled with mass spectrometry (GC-MS) have been developed for the determination of guaiazulene (GA) in complex matrices such as creams and toothpastes. A solid phase extraction (SPE)
A P Kourounakis et al.
The Journal of pharmacy and pharmacology, 49(9), 938-942 (1997-11-05)
The effect of guaiazulene, a lipophilic azulene derivative widely found in nature, on radical-mediated processes is examined. The ability of guaizulene to inhibit rat hepatic microsomal membrane lipid peroxidation and to scavenge hydroxyl radicals, as well as to interact with
Photophysical, electrochemical, and photoelectrochemical properties of new azulene-based dye molecules.
Zhang XH, et al.
Journal of Materials Chemistry, 17(7), 642-649 (2007)
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