4-Hexylresorcin

Bezeichnung:4-Hexylresorcin

CAS-Nr136-77-6

Englisch Name:4-Hexylresorcinol

CBNumberCB2725396

SummenformelC12H18O2

Molgewicht194.27

MOL-Datei136-77-6.mol

Synonyma

4-Hexylresorcin

4-Hexylresorcin physikalisch-chemischer Eigenschaften

Schmelzpunkt	65-67 °C (lit.)
Siedepunkt	333-335 °C (lit.)
Dichte	1.0010 (rough estimate)
Dampfdruck	0.001Pa at 25℃
Brechungsindex	1.5050 (estimate)
Flammpunkt	>100°C
storage temp.	2-8°C
Löslichkeit	chloroform: 50 mg/mL, clear
pka	pKa 9.1 (Uncertain)
Aggregatzustand	Powder and/or Chunks
Farbe	White to pale orange or pale pink
PH	7.7 (0.5g/l, H2O, 20℃)
Wasserlöslichkeit	0.05 g/100 mL (18 ºC)
Merck	14,4712
BRN	2048312
Stabilität	Stable. Incompatible with acid chlorides, acid anhydrides, oxidizing agents.
InChIKey	WFJIVOKAWHGMBH-UHFFFAOYSA-N
LogP	3.34 at 20℃
Oberflächenspannung	36.59mN/m at 1g/L and 20℃
CAS Datenbank	136-77-6(CAS DataBase Reference)
NIST chemische Informationen	Hexylresorcinol(136-77-6)
EPA chemische Informationen	4-Hexylresorcinol (136-77-6)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38-20/21/22
S-Sätze:	26-36-24/25
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
RTECS-Nr.	VH1575000
TSCA	Yes
HS Code	29072900
Giftige Stoffe Daten	136-77-6(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 550 mg/kg

Gefahreninformationscode (GHS)

4-Hexylresorcinol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
slightly red powder
Verwenden
4-Hexylresorcinol is an inhibitor of transglutaminase-2 in KB cells. Studies indicate that 4-Hexylresorcinol reduces DNA oxidative damage in human lymphocytes. is a substituted dihydroxybenzene used topically as an antiseptic for the treatment of minor skin infections. is a substituted phenol with bactericidal, antihelminthic and potential antineoplastic activities. The combination of 4-Hexylresorcinol and Cisplatin has been shown to inhibit tumor growth, cell growth, and KB cell viability.
Verwenden
4-Hexylresorcinol is used as the starting material to synthesize a potent immune suppressor, celastramycin A. It is a precursor to prepare resorcinol-sn-glycerol derivatives, that exhibit high affinity for cannabinoid type 1 receptor. It can also be incorporated as a linker while building catenanes. p-Hexylresorcinol shows antiimnflammatory activity acting on the human 5-LO (5-Lipoxygenase) proinflammatory enzyme.
synthetische
The preparation of 4-Hexylresorcinol involves two methods:
The reaction of caproic acid and resorcinol in the presence of a catalyst.
Reduction of hexanoylresorcinol with zinc amalgam and dilute hydrochloric acid.
Definition
ChEBI: 4-hexylbenzene-1,3-diol is a member of resorcinols.
Allgemeine Beschreibung
P-hexylresorcinol appears as pale-yellow viscous liquid (that becomes solid on standing at room temperature) or a peach colored powder. Pungent faintly fatty odor. Sharp astringent taste. (NTP, 1992)
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
4-Hexyl-1,3-benzenediol may be sensitive to prolonged exposure to light. Incompatible with acid chlorides, acid anhydrides and oxidizing agents .
Hazard
Irritant to respiratory tract and skin, concentrated solutions are vesicant.
Brandgefahr
Flash point data for 4-Hexyl-1,3-benzenediol are not available. 4-Hexyl-1,3-benzenediol is probably combustible.
Biologische Aktivität
hexylresorcinol is a mushroom tyrosinase inhibitor.tyrosinase, a copper-containing enzyme, is distributed in microorganisms, animals, and plants widely. mushroom tyrosinase has been becoming popular due to its availability and usages in various applications.
Clinical Use
Hexylresorcinol, also known as 4-hexylresorcinol, is a white crystalline substance with a faint phenolic odor. When applied to the tongue it produces a sensation of numbness. It is freely soluble in alcohol but only slightly soluble in water(1–20,000 parts). Hexylresorcinol is an effective antiseptic,possessing both bactericidal and fungicidal properties.The phenol coefficient of hexylresorcinol against S. aureusis 98. As is typical for alkylated phenols, hexylresorcinol possesses surfactant properties. The compound also haslocal anesthetic activity. Hexylresorcinol is formulated into throat lozenges because of its local anesthetic and antisepticproperties. These preparations are probably of little value. Hexylresorcinol (in the concentration in thelozenge) is probably not antiseptic, and the local anestheticproperty can anesthetize the larynx, causing temporary laryngitis.
in vitro
previous results showed hexylresorcinol could inhibit both mono- and di-phenolase activity of mushroom tyrosinase. moreover, hexylresorcinol at 2 μm lengthened the lag period from 98 s to 26. hexylresorcinol could also display reversible inhibition of the enzyme. in addition, the kinetic analyses showed that hexylresorcinol was a competitive inhibitor with the apparent inhibition constant binding with free enzyme to be 0.443 μm for diphenolase [1].
in vivo
previous in vivo study showed that hexylresorcinol could induce chromosome aberrations in mouse eukaryotic cells at doses of 0.5, 0.05, and 0.005 mg/g and the metabolic transformation of hexylresorcinol decreased its genotoxic effect in mice. moreover, the mutagenic effect lasted for 3 days only at the highest dose of hexylresorcinol (0.5 mg/g). thus, hexylresorcinol doses less than 0.5 mg/g were metabolized within two days to the extent of the cytotoxic effect. in addition, hexylresorcinol was transformed at a rate of 0.0025–0.025 mg/day after a single administration to mice [2].
IC 50
1.24 μm
Einzelnachweise
[1] chen qx,ke ln,song kk,huang h,liu xd. inhibitory effects of hexylresorcinol and dodecylresorcinol on mushroom (agaricus bisporus) tyrosinase. protein j.2004 feb;23(2):135-41.
[2] margulis ab,ozhiganova iv,bushmanova ov,kolpakov ai,il'inskaia on. hexylresorcinol induces chromosome aberrations in mouse peripheral blood cells. genetika. 2005 aug;41(8):1045-8.

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