Guaiazulene

Guaiazulene
IUPAC name 1,4-dimethyl-7-isopropylazulene
Identifiers
CAS number	489-84-9 Y
PubChem	3515
ChemSpider	3395 Y
UNII	2OZ1K9JKQC Y
KEGG	D01037 Y
ChEBI	CHEBI:5550 Y
Jmol-3D images	Image 1
SMILES CC(C)c2cc1c(ccc1C)c(C)cc2
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 Y Key: FWKQNCXZGNBPFD-UHFFFAOYSA-N Y InChI=1/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3 Key: FWKQNCXZGNBPFD-UHFFFAOYAG
Properties
Molecular formula	C15H18
Molar mass	198.31 g/mol
Density	0.976 g/cm3
Melting point	31-33 °C
Boiling point	153 °C (7 mm Hg)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Guaiazulene, also azulon or 1,4-dimethyl-7-isopropylazulene, is a dark blue crystalline hydrocarbon. A derivative of azulene, guaiazulene is a bicyclic sesquiterpene that is a constituent of some essential oils, mainly oil of guaiac and chamomile oil, which also serve as its commercial sources. Various soft corals also contain guaiazulene as a principal pigment. Its low melting point makes guaiazulene difficult to handle, in contrast to the crystalline nature of the parent azulene. The electronic structure (and colors) of guaiazulene and azulene are very similar.

The blue color of the mushroom Lactarius indigo is due to the guaiazulene derivative (7-isopropenyl-4-methylazulen-1-yl)methyl stearate.

Applications

Guaiazulene is an U.S. FDA-approved cosmetic color additive. It - or its 3-sulfonate - is a component of some skin care products together with other skin soothing compounds such as allantoin.

Guaiazulene has applications as an anti-ulcer drug, and can be also used as a volatile dye with a known evaporation rate to indicate end of use of various products (such as insecticide strips)^{[citation needed]}