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Ophthalmology drugs
Guaiazulene
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Guaiazulene

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Guaiazulene
Guaiazulene
Names
Preferred IUPAC name
1,4-Dimethyl-7-(propan-2-yl)azulene
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.002
KEGG
PubChem CID
UNII
  • InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3 checkY
    Key: FWKQNCXZGNBPFD-UHFFFAOYSA-N checkY
  • 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
  • CC1=C2C=CC(=C2C=C(C=C1)C(C)C)C
Properties
C15H18
Molar mass 198.309 g·mol−1
Density 0.976 g/cm3
Melting point 31 to 33 °C (88 to 91 °F; 304 to 306 K)
Boiling point 153 °C (307 °F; 426 K) (7 mm Hg)
Pharmacology
S01XA01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Guaiazulene solution
Guaiazulene solution in DMSO with hydroquinone added as an antioxidant

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.

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 some skin care products together with other skin soothing compounds such as allantoin.

Guaiazulene has applications as a volatile dye with a known evaporation rate to indicate end of use of various products (such as insecticide strips).

Attempts to capitalize on the structure of Guaiazulene had led to Hns-32 [186086-10-2].


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