Monobenzon

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H317：Kann allergische Hautreaktionen verursachen.

  H319：Verursacht schwere Augenreizung.

• Sicherheit

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Monobenzone Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R36:Reizt die Augen.
  R43:Sensibilisierung durch Hautkontakt möglich.

• S-Sätze Betriebsanweisung:

  S24/25:Berührung mit den Augen und der Haut vermeiden.
  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S37:Geeignete Schutzhandschuhe tragen.

• Beschreibung

  4-(Benzyloxy)phenol, also called monobenzone and monobenzyl ether of hydroquinone (MBEH) is an organic chemical in the phenol family with chemical formula C6H5CH2OC6H4OH. It is used as a topical drug for medical depigmentation. Monobenzone occurs as a white, almost tasteless crystalline powder, soluble in alcohol and practically insoluble in water.
  The topical application of monobenzone in animals, increases the excretion of melanin from the melanocytes. The same action is thought to be responsible for the depigmenting effect of the drug in humans.

• Chemische Eigenschaften

  4-Benzyloxyphenol is a cream to beige-light brownish crystals classified as a hydroquinone monobenzyl ether. It is soluble in alcohol, benzene and ether, and almost insoluble in water. 4-Benzyloxyphenol is a depigmenting agent that has the effect of enhancing the rate of elimination of melanin secreted by skin cells, and studies have shown that the molecular mechanism of its action may be related to tyrosinase.

• Verwenden

  4-Benzyloxyphenol is used in the synthesis of bis(4-benzyloxyphenoxy)phenyl phosphine oxide. It plays an essential role in the preparation of hetaryl-azophenol dyes via heterocyclic amines in nitrosyl sulphuric acid. It is also used for polyester fiber dyeing and in rubber industry. It acts as a depigmenting agent.

• Verwenden

  Hydroquinone monobenzyl ether is an antidegradant added to rubber products; inhibitor in acrylic resins.

• Verwenden

  PBP is used as antiinflammatory, antisecretory, antiulcer.

• synthetische

  4-Benzyloxyphenol Synthesis: Add 2.63g (0.028mol) of hydroquinone to a 100mL conical flask, weigh 1.12g (0.028mol) of sodium hydroxide, add 8mL of water, wait for the sodium hydroxide to dissolve and add dropwise to the conical flask with hydroquinone, shake well, then add 15mL of DMF and 2.52g (0.02mol) of benzyl chloride, under microwave radiation power of 320W The reaction was cooled to room temperature at the end of the reaction. The reaction was first adjusted to alkalinity with 10% sodium hydroxide, filtered, and the filtrate was washed with 10% sodium hydroxide until the filtrate was colorless (the filtrate was hydroquinone bis(benzyl ether), which could be recycled). The filtrate was acidified with hydrochloric acid to make Monobenzone completely precipitated, and then washed by filtration and ice water, recrystallized with alcohol and water, and decolorized by activated carbon to obtain 2.55g of white solid, the yield was 63.79%.

• Indications

  Monobenzone (Benoquin) potently inhibits melanin production and destroys melanocytes. Like hydroquinone, monobenzone was originally introduced for the topical treatment of disorders of excess melanin pigmentation, including melasma. It is now used only to permanently depigment the remaining normally pigmented skin in patients with extensive vitiligo. Irritant and allergic contact dermatitis are common side effects.

• Definition

  ChEBI: Monobenzone is the monobenzyl ether of hydroquinone. It is used as a topical drug for medical depigmentation. It has a role as a melanin synthesis inhibitor, a dermatologic drug and an allergen. It derives from a hydroquinone.

• Trademarks

  Benoquin (Valeant).

• Origin

  Monobenzone (monobenzyl ether of hydroquinone, MB) is a depigmenting agent that was discovered by Oliver et al. in 1939. It has been approved by the FDA as a cream formulation for skin depigmentation of patients with vitiligo. The mechanism of action for depigmentation by MB is correlated with the inhibition of tyrosinase[1]. The compound also is cytotoxic to melanocytes and melanoma cells and increases melanocyte and melanoma cell immunogenicity.

• Synthesis Reference(s)

  Tetrahedron Letters, 33, p. 5129, 1992 DOI: 10.1016/S0040-4039(00)61209-1

• Biologische Aktivität

  The skin-depigmenting effect of MB is correlated with the inhibition of tyrosinase, the rate-limiting enzyme in melanin synthesis, in both melanocytes and melanoma cells. The metabolites of MB have been proven to exert toxic effects on melanocytes and increase melanocyte and melanoma cell immunogenicity. MB potently inhibited RNR enzyme activity by targeting RRM2 and thereby suppressed AML cell growth in vitro and in a mouse xenograft experiment[1-2].

• Nebenwirkungen

  Side effects:
  Allergic reaction: Itching or hives, swelling in your face or hands, swelling or tingling in your mouth or throat, chest tightness, trouble breathing
  Intense itching, blistering, burning, or swelling of the skin.
  Mild skin rash, tenderness, or redness.

• läuterung methode

  Crystallise it from EtOH or H2O, and dry (P2O5) under vacuum. [Walter et al. J Am Chem Soc 108 5210 1986, Beilstein 6 IV 5778.]

• Einzelnachweise

  [1] Jingwen Dong. “Identification of Monobenzone as a Novel Potential Anti-Acute Myeloid Leukaemia Agent That Inhibits RNR and Suppresses Tumour Growth in Mouse Xenograft Model.” Cancers (2022).
  [2] Jasper G. van den Boorn . “Skin-Depigmenting Agent Monobenzone Induces Potent T-Cell Autoimmunity toward Pigmented Cells by Tyrosinase Haptenation and Melanosome Autophagy.” Journal of Investigative Dermatology 131 6 (2011): Pages 1240-1251.

Monobenzone Upstream-Materialien And Downstream Produkte

Monobenzon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(626)Suppliers

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