Guaiazulene

Guaiazulene

Names
IUPAC name 1,4-Dimethyl-7-isopropylazulene
Identifiers
CAS Number	489-84-9
ChEBI	CHEBI:5550
ChEMBL	ChEMBL1408759
ChemSpider	3395
Jmol interactive 3D	Image
KEGG	D01037
PubChem	3515
UNII	2OZ1K9JKQC
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	198.31 g·mol^−1
Density	0.976 g/cm^3
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
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

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.
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.