Guaiazulene

Summary

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.

Guaiazulene
Guaiazulene
Names
Preferred IUPAC name
1,4-Dimethyl-7-(propan-2-yl)azulene
Identifiers
  • 489-84-9 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • L00520
ChEBI
  • CHEBI:5550 checkY
ChEMBL
  • ChEMBL1408759 ☒N
ChemSpider
  • 3395 checkY
ECHA InfoCard 100.007.002 Edit this at Wikidata
KEGG
  • D01037 checkY
  • 3515
UNII
  • 2OZ1K9JKQC checkY
  • DTXSID7045996 Edit this at Wikidata
  • 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).
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Infobox references
The blue color of the mushroom Lactarius indigo is due to the guaiazulene derivative (7-isopropenyl-4-methylazulen-1-yl)methyl stearate.[2]

A similar structure Alismol is in a different oxidation state.

ApplicationsEdit

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]

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

ReferencesEdit

  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.{{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. doi:10.1046/j.1468-3083.2001.00340.x. PMID 11763400.