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Merck
CN

G11004

Guaiazulene

99%

Synonym(s):

1,4-Dimethyl-7-isopropylazulene

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About This Item

Empirical Formula (Hill Notation):
C15H18
CAS Number:
Molecular Weight:
198.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-701-2
Beilstein/REAXYS Number:
1365001
MDL number:
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Product Name

Guaiazulene, 99%

InChI key

FWKQNCXZGNBPFD-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

99%

bp

153 °C/7 mmHg (lit.)

mp

27-29 °C (lit.)

density

0.976 g/mL at 25 °C (lit.)

Quality Level

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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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Y Seo et al.
Journal of natural products, 59(10), 985-986 (1996-10-01)
Three pigments of the guaiazulene class have been isolated from the gorgonian Calicogorgia granulosa. Structures of these compounds have been determined as guaiazulene, 2,2'- diguaiazulenylmethane, and a new compound, 2,2'-biguaiazulenyl, by combined chemical and spectroscopic methods. 2,2'-Biguaiazulenyl exhibited moderate antimicrobial
Stilbazulenyl nitrone (STAZN): a nitronyl-substituted hydrocarbon with the potency of classical phenolic chain-breaking antioxidants.
Becker DA, et al.
Journal of the American Chemical Society, 124(17), 4678-4684 (2002)
Jessica Fiori et al.
Rapid communications in mass spectrometry : RCM, 22(17), 2698-2706 (2008-08-06)
The photostability of guaiazulene (1,4-dimethyl-7-isopropylazulene; GA), a natural azulenic compound used in cosmetic and health-care products, as well as in pharmaceutical preparations, was investigated in solution (methanol, ethanol, acetonitrile), by different techniques: gas chromatography/mass spectrometry (GC/MS) and high-performance liquid chromatography
E Dovolou et al.
Reproduction in domestic animals = Zuchthygiene, 46(5), 862-869 (2011-02-18)
Reactive oxygen species (ROS) are between the major contributors for the reduced rate of in vitro bovine embryo production. It is believed that they can cause abnormal meiosis of oocytes, developmental arrest or cell death of embryos. Reports on the
Determination of the ophthalmic drug guaiazulene by high-performance liquid chromatography.
E Vidal-Ollivier et al.
Journal of chromatography, 463(1), 227-228 (1989-01-20)

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