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Guaiazulene, also azulon or 1,4-dimethyl-7-isopropylazulene, is a dark blue crystalline 
A similar structure Alismol is in a different oxidation state.
Guaiazulene, also azulon or 1,4-dimethyl-7-isopropylazulene, is a dark blue crystalline hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...
. A derivative
In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...
of azulene
Azulene is an organic compound and an isomer of naphthalene. Naphthalene is colourless, whereas azulene is dark blue. Two terpenoids, vetivazulene (4,8-dimethyl-2-isopropylazulene) and guaiazulene (1,4-dimethyl-7-isopropylazulene), that featur ...
, guaiazulene is a bicyclic sesquiterpene
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modificat ...
that is a constituent of some essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
s, mainly oil of guaiac and chamomile
Chamomile (American English) or camomile (British English; see spelling differences) ( or ) is the common name for several plants of the family Asteraceae. Two of the species, ''Matricaria recutita'' and ''Anthemis nobilis'', are commonly us ...
oil, which also serve as its commercial sources. Various soft coral
Alcyonacea, or soft corals, are an order of corals. In addition to the fleshy soft corals, the order Alcyonacea now contains all species previously known as "gorgonian corals", that produce a more or less hard skeleton, though quite different f ...
s 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.
A similar structure Alismol is in a different oxidation state.Applications
Guaiazulene is an U.S. FDA-approved cosmetic color additive. It – or its 3-sulfonate – is a component of someskin care
Skin care is a range of practices that support skin integrity, enhance its appearance, and relieve skin conditions. They can include nutrition, avoidance of excessive sun exposure, and appropriate use of emollients. Practices that enhance appea ...
products together with other skin soothing compounds such as allantoin
Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacter ...
.
Guaiazulene has applications as a volatile dye with a known evaporation rate to indicate end of use of various products (such as insecticide strips).{{Fact, date=May 2009
Attempts to capitalize on the structure of Guaiazulene had led to Hns-32 86086-10-2
References