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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/05/10 17:37:41」(JST)

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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.

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

Applications [edit]

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 an anti-ulcer drug, and can be also used as a volatile dye with a known evaporation rate to indicate end of use of various products (such as insecticide strips)^{[citation needed]}

References [edit]

^ B.F. Bowden, J.C. Coll, and D.M. Tapiolas "Studies of Australian soft corals. XXX. A novel trisnorsesquiterpene from a Cespitularia species and the isolation of guaiazulene from a small blue Alcyonium species" Australian Journal of Chemistry 1983, Volume 36, pages 211 – 214. doi:10.1071/CH9830211
^ Harmon AD, Weisgraber KH, Weiss U. (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.
^ M. Guarrera, L. Turbino, A. Rebora "The Anti-Inflammatory Activity of Azulene" Journal of the European Academy of Dermatology and Venereology, 2001, volume 15, pages 486–487. doi:10.1046/j.1468-3083.2001.00340.x

English Journal

Assessment of the antioxidant and antiproliferative effects of sesquiterpenic compounds in in vitro Caco-2 cell models.

Vinholes J1, Gonçalves P2, Martel F2, Coimbra MA1, Rocha SM3.
Food chemistry.Food Chem.2014 Aug 1;156:204-11. doi: 10.1016/j.foodchem.2014.01.106. Epub 2014 Feb 7.
In this study, the antiradical and antiproliferative effects of the sesquiterpenic compounds trans, trans-farnesol, cis-nerolidol, α-humulene and guaiazulene, commonly found in plants and plant-derived foods and beverages, were evaluated. Chemical (DPPH and hydroxyl radicals) and biological (Caco-2
PMID 24629959

In vitro antimicrobial activities of cinnamon bark oil, anethole, carvacrol, eugenol and guaiazulene against Mycoplasma hominis clinical isolates.

Sleha R1, Mosio P, Vydrzalova M, Jantovska A, Bostikova V, Mazurova J.
Biomedical papers of the Medical Faculty of the University Palacký, Olomouc, Czechoslovakia.Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub.2014 Jun;158(2):208-11. doi: 10.5507/bp.2012.083. Epub 2012 Oct 30.
AIMS: The aim of this study was to evaluate the antimicrobial effects of five natural substances against 50 clinical isolates of Mycoplasma hominis.METHODS AND RESULTS: The in vitro activity of selected natural compounds, cinnamon bark oil, anethole, carvacrol, eugenol and guaiazulene, was investiga
PMID 23128812

Ochracenoids A and B, guaiazulene-based analogues from gorgonian Anthogorgia ochracea collected from the South China Sea.

Zheng JJ1, Shao CL2, Chen M3, Gan LS4, Fang YC5, Wang XH6, Wang CY7.
Marine drugs.Mar Drugs.2014 Mar 14;12(3):1569-79. doi: 10.3390/md12031569.
Two new guaiazulene-based analogues, ochracenoids A (1) and B (2), along with four known analogues (3-6), were isolated from the gorgonian Anthogorgia ochracea collected from the South China Sea. The planar structures of the new compounds were elucidated by comprehensive spectroscopic data. The abso
PMID 24637960

Japanese Journal

ONE-POT SYNTHESIS OF (GUAIAZULEN-1-YL)FURAN DERIVATIVES FROM GUAIAZULENE AND 1,4-DIARYL-2-BUTENE-1,4-DIONES

Wang Dao-Lin,Yu Jia-Yi,Xu Jiao [他]
Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 87(5), 1099-1108, 2013-05-01
NAID 40019640936

FACILE SYNTHESIS OF GUAIAZULENE-HETEROCYCLE HYBRIDS VIA MULTICOMPONENT REACTIONS INVOLVING FORMATION OF ZWITTERIONIC INTERMEDIATES

Sato Koichi,Yokoo Erina,Takenaga Naoko
Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 87(4), 807-814, 2013-04-01
NAID 40019621898

Synthesis of New Azulene Derivatives and Study of Their Effect on Lipid Peroxidation and Lipoxygenase Activity

Rekka Eleni,Chrysselis Michael,Siskou Ioanna [他],KOUROUNAKIS Angeliki
Chemical & pharmaceutical bulletin 50(7), 904-907, 2002-07-01
… We have previously reported the significant antioxidant activity of the natural azulene derivatives chamazulene and guaiazulene. …
NAID 110003616272

「ジメチルイソプロピルアズレン」

Guaiazulene
	IUPAC name 1,4-dimethyl-7-isopropylazulene
Identifiers
CAS number	489-84-9
PubChem	3515
ChemSpider	3395
UNII	2OZ1K9JKQC
KEGG	D01037
ChEBI	CHEBI:5550
Jmol-3D images	Image 1
	SMILES CC(C)c2cc1c(ccc1C)c(C)cc2 ;
	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 ;
Properties
Molecular formula	C15H18
Molar mass	198.31 g/mol
Density	0.976 g/cm3
Melting point	31-33 °C
Boiling point	153 °C (7 mm Hg)
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references