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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/REAXYS Number:
1365001
EC Number:
207-701-2
MDL number:
MFCD00003811
UNSPSC Code:
12352100
PubChem Substance ID:
24895038
NACRES:
NA.22

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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

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

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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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)
Jessica Fiori et al.
Toxicology in vitro : an international journal published in association with BIBRA, 25(1), 64-72 (2010-09-22)
Guaiazulene (GA) is widely used as a natural ingredient in many health care products and solutions. Although it has been reported to have interesting biological effects, GA and azulene derivatives have been proven to be cytotoxic against normal human cells
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
Graziano Guella et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 9(23), 5770-5777 (2003-12-16)
It is shown here that calenzanane sesquiterpenes (1 and 6) can be isolated from organic extracts from the red seaweed Laurencia microcladia Kützing from the Bay of Calenzana, Elba Island, provided contact with acidic media is minimized. Such contact induces
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)
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