Monobenzone

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Cat Number

API0232268

CAS Number

103-16-2

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CAS Number

103-16-2

EINECS

203-083-3

Storage

Store at 2-8°C

Synonyms

4-(Benzyloxy)phenol; Hydroquinone monobenzyl ether; Benoquin; P-(BENZYLOXY)PHENOL; Benzoquin; Leucodinine; Monobenzon

Molecular Formula

C13H12O2

Molecular Weight

200.23

Smiles

C1=CC=C(C=C1)COC2=CC=C(C=C2)O

Appearance

White powder or crystal

Melting Point

119-120°C (lit.)

Boiling Point

297.96°C (Estimate)

Relative Density

1.26

General Description

Monobenzone is a synthetic organic compound with a benzyl ether structure, chemically related to hydroquinone. Its chemical structure is 4-[(4-hydroxyphenyl)methyl]phenol, or p-hydroxybenzyl ether. Monobenzone is a white to off-white crystalline powder, practically insoluble in water but soluble in organic solvents. It is a skin depigmenting agent.

Mechanism of Action

Monobenzone acts by inhibiting the enzyme tyrosinase, which is essential for the synthesis of melanin in melanocytes. It also causes the destruction of melanocytes by inducing the formation of antibodies against melanocytes, leading to a permanent loss of pigment. The drug is a potent depigmenting agent that is effective in completely removing skin color.

Application

Monobenzone is indicated for the treatment of extensive vitiligo, particularly in patients with widespread depigmentation who are resistant to other therapies. It is used to achieve total depigmentation of the skin, providing a uniform appearance. The drug is also used for the treatment of post-inflammatory hyperpigmentation and other pigmentary disorders.

Monobenzone, a topical depigmenting agent, was identified as a reversible, competitive inhibitor of lysine‑specific demethylase 1 (KDM1A) with IC₅₀ 0.45 μM. It inhibited proliferation of gastric cancer cells, increased H3K4me1/2 and H3K9me2 levels, and reversed epithelial‑mesenchymal transition. This simple small molecule provides a novel scaffold for KDM1A inhibitor development and a potential new indication for monobenzone.

Fig. 1 Monobenzone inhibits KDM1A in a reversible manner. (Ma P, et al., 2021)

References

Ma P, et al. Monobenzone, a Novel and Potent KDM1A Inhibitor, Suppresses Migration of Gastric Cancer Cells. Front Pharmacol. 2021;12:640949.

In a phase II trial of 25 patients with stage III-IV melanoma and non-resectable cutaneous metastases, topical monobenzone combined with imiquimod (MI therapy) was well tolerated. At 12 weeks, partial regression occurred in 8 patients (38%). With prolonged therapy, clinical response was seen in 11 patients (including 3 complete responses). Seven patients developed vitiligo-like depigmentation at untreated sites. Melanoma-specific antibody and CD8+ T-cell responses were induced in responding patients. MI therapy is a low-cost, broadly applicable treatment for cutaneous melanoma metastases.

Fig. 2 Local clinical responses of treated cutaneous metastases. (Teulings HE, et al., 2018)

References

Teulings HE, et al. Anti-Melanoma immunity and local regression of cutaneous metastases in melanoma patients treated with monobenzone and imiquimod; a phase 2 a trial. Oncoimmunology. 2018;7(4):e1419113.

Does Monobenzone require protection from light and oxygen during storage?

Yes, it is sensitive to light and oxygen. The hydroquinone moiety readily oxidizes to quinone derivatives. Store in airtight, light-resistant containers under inert gas.

What is the recommended storage temperature for Monobenzone?

Store at 2-8°C (refrigerated). At room temperature, rapid oxidation and discoloration occur, reducing depigmenting activity.

Is Monobenzone stable in topical cream and solution formulations?

Formulations require antioxidants (e.g., sodium metabisulfite) and protection from light.

How is the impurity p-benzoquinone (an oxidative degradation product) monitored?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains below pharmacopoeial limits.