Guaiazulene

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Guaiazulene
Guaiazulene Guajazulene skeletal.svg
Guaiazulene
Names
Preferred IUPAC name
1,4-Dimethyl-7-(propan-2-yl)azulene
Identifiers
3D model (JSmol)
1365001
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.002 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-701-2
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 Yes check.svgY
    Key: FWKQNCXZGNBPFD-UHFFFAOYSA-N Yes check.svgY
  • 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).
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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. [1] 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.

Applications

The blue color of the mushroom Lactarius indigo is due to the guaiazulene derivative (7-isopropenyl-4-methylazulen-1-yl)methyl stearate. Lactarius indigo 48568 edit.jpg
The blue color of the mushroom Lactarius indigo is due to the guaiazulene derivative (7-isopropenyl-4-methylazulen-1-yl)methyl stearate.
Guaiazulene solution in DMSO with hydroquinone added as an antioxidant Gvaiazulen.jpg
Guaiazulene solution in DMSO with hydroquinone added as an antioxidant

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. [3]

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

References

  1. ↑ Bowden, BF; Coll, JC; Tapiolas, DM (1983). "Studies of Australian soft corals. XXX. A novel trisnorsesquiterpene from a Cespitulariaspecies and the isolation of guaiazulene from a small blue Alcyoniumspecies". Australian Journal of Chemistry. 36: 211. doi:10.1071/CH9830211.
  2. ↑ Harmon AD, Weisgraber KH, Weiss U.; Weisgraber; Weiss (1979). "Preformed azulene pigments of Lactarius indigo (Schw.) Fries (Russulaceae, Basidiomycetes)". Cellular and Molecular Life Sciences. 36 (1): 54–56. doi:10.1007/BF02003967. ISSN   1420-682X. S2CID   21207966.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ↑ Guarrera, M; Turbino, L; Rebora, A (2001). "The anti-inflammatory activity of azulene". Journal of the European Academy of Dermatology and Venereology. 15 (5): 486–487. doi:10.1046/j.1468-3083.2001.00340.x. PMID   11763400. S2CID   34050487.
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