Guaiazulene

Guaiazulene
Names
	IUPAC name 1,4-Dimethyl-7-isopropylazulene
Identifiers
CAS Number	489-84-9 ;
3D model (JSmol)	Interactive image;
3DMet	L00520;
ChEBI	CHEBI:5550 ;
ChEMBL	ChEMBL1408759 ;
ChemSpider	3395 ;
ECHA InfoCard	100.007.002
KEGG	D01037 ;
PubChem CID	3515;
UNII	2OZ1K9JKQC ;
CompTox Dashboard (EPA)	DTXSID7045996 ;
	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 Key: FWKQNCXZGNBPFD-UHFFFAOYSA-N ; 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;
	SMILES CC1=C2C=CC(=C2C=C(C=C1)C(C)C)C;
Properties
Chemical formula	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
ATC code	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

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.

The blue color of the mushroom Lactarius indigo is due to the guaiazulene derivative (7-isopropenyl-4-methylazulen-1-yl)methyl stearate.[2]

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.[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).

References

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.
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.CS1 maint: multiple names: authors list (link)
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.

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[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.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.