2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-on

Bezeichnung:2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-on

CAS-Nr499-44-5

Englisch Name:Hinokitiol

CBNumberCB8714323

SummenformelC10H12O2

Molgewicht164.2

MOL-Datei499-44-5.mol

Synonyma

2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-on

2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	50-52 °C(lit.)
Siedepunkt	140 °C10 mm Hg(lit.)
Dichte	1.0041 (rough estimate)
Brechungsindex	1.5190 (estimate)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
Aggregatzustand	solid
pka	7.06±0.30(Predicted)
Farbe	White
Geruch (Odor)	at 100.00 %. phenolic woody mossy
Geruchsart	woody
Merck	14,9390
Stabilität	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 4 months.
LogP	1.137 (est)
CAS Datenbank	499-44-5(CAS DataBase Reference)
NIST chemische Informationen	2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-(499-44-5)
EPA chemische Informationen	2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- (499-44-5)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22
S-Sätze:	36
WGK Germany	3
RTECS-Nr.	GU4200000
HS Code	2914290090

Gefahreninformationscode (GHS)

Hinokitiol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins.Hinokitiol is used in oral and skin care products,and is a food additive used in Japan.
Verwenden
Antibacterial additive in foods, cosmetics, eye drops and toothpaste.
Verwenden
Hinokitiol is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol has inhibitory effects on Chlamydia trachomatis and may be clinically useful as a topical drug.
Definition
ChEBI: A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.
Anticancer Research
Studied in xenograft tumors such lung adenocarcinoma cell, EGFR-TKI-resistantlines PC9-IR and H1975 in which the growth inhibition was observed, a novel antitumormechanism was hypothesized. In summary, the hinokitiol can induce DNAdamage and autophagy (Rodrigues et al. 2015).
Einzelnachweise
1) Ido et al (1999) Induction of apoptosis by hinokitiol, a potent iron chelator, in teratocarcinoma F9 cells is mediated through the activation of caspase-3; Cell Prolif., 32 63 2) Suzuki et al. (2000) Hinokitiol, a selective inhibitor of the platelet-type isozyme of arachidonate 12-lipoxygenase; Biochem. Biophys. Res. Commun., 275 885 3) Morita et al. (2007) The mechanism of the bactericidal activity of hinokitiol; Biocontrol Sci., 12 101 4) Liu and Yamauchi (2006) Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carcinoma cell lines; Biochem. Biophys. Res. Commun., 351 26 5) Lee et al. (2010) Hinokitiol activates the hypoxia-inducible factor (HIF) pathway through inhibition of HIF hydroxylases; Biochem. Biophys. Res. Commun., 396 370

Hinokitiol Upstream-Materialien And Downstream Produkte

2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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