Guaiaculen

Structural formula
General
Surname	Guaiaculen
other names	7-isopropyl-1,4-dimethylazulene Azulon
Molecular formula	C 15 H 18
Brief description	dark blue crystals with a low melting point
External identifiers / databases
CAS number 489-84-9 EC number 207-701-2 ECHA InfoCard 100.007.002 PubChem 3515 Wikidata Q3026266
properties
Molar mass	198.30 g mol −1
Physical state	firmly
density	0.976 g cm −3 (25 ° C)
Melting point	27-29 ° C
boiling point	153 ° C (7 mmHg ) 320 ° C
solubility	poorly soluble in water soluble in ethanol , diethyl ether and ethyl acetate
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302 P: no P-phrases
Toxicological data	1550 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Guaiaculene (from guaiac and French: azure "blue") or 7-isopropyl-1,4-dimethylazulene , also azulone , is a blue crystalline aromatic hydrocarbon that is used in particular in cosmetics and medicine.

properties

At approx. 600 µg / kg, guaiacol is only sparingly soluble in water. But it is soluble in ethanol , diethyl ether and ethyl acetate .

Pure guajazulene consists of blue crystals, but liquid solutions or mixtures with solid and liquid components are mainly available on the market. Guajazulen is almost odorless.

Guajazulene can have local anti-inflammatory and antiallergic effects. However, whether this has any therapeutic benefit is controversial.

Occurrence

Guaiaculene is obtained either from gujaol , the essential component of the oil from Bulnesia sarmientoi and other tree species closely related to the guaiac tree, or from caryophylls , a component of clove oil .

use

Guajazulene (7-isopropyl-1,4-dimethylazulene) is often used as a substitute for chamazulene (1,4-dimethyl-7-ethylazulene), an essential component of chamomile oil , as it has very similar properties but is cheaper to manufacture.

In cosmetics , guajazulene is often a component of ointments or creams for skin care.

It is used medically both internally, against inflammation in the gastrointestinal tract, the respiratory tract or the skin, and externally, against inflammation of the skin or sunburn.

Individual evidence

1. ↑ ^{a b} Entry on guajazulene at TCI Europe, accessed on March 1, 2015.
2. ↑ ^{a b c d e f g} data sheet guaiazulene, 99% from Sigma-Aldrich , accessed on March 1, 2015 ( PDF ).
3. ↑ ^{a b c d} Ernst Steinegger, Rudolf Hansel: Pharmakognosie . Springer-Verlag, 2013, ISBN 978-3-662-09267-5 , pp. 1048 ( limited preview in Google Book search).
4. ^ ^{A b} William M. Haynes: CRC Handbook of Chemistry and Physics, 96th Edition . CRC Press, 2015, ISBN 978-1-4822-6097-7 ( limited preview in Google Book Search).
5. ↑ See Septimus Piesse : On the Coloring Principle of Volatile Oils . In: Chemical News . No. 8 , 1863, p. 245 ( online [accessed March 2, 2015]).
6. ↑ Joel Reza, Arturo Trejo, Luz Elena Vera-Ávila: Determination of the temperature dependence of water solubilities of polycyclic aromatic hydrocarbons by a generator column-on-line solid-phase extraction-liquid chromatographic method . In: Chemosphere . No. 47 , 2002, p. 933–945 ( online [PDF; accessed March 2, 2015]).
7. ^ ^{A b c} Rudolf Hansel, Joseph Hölzl: Textbook of pharmaceutical biology. Springer-Verlag, 1996, p. 75.