Monobenzone

A topical depigmenting agent used for permanent depigmentation of residual normally pigmented skin in patients with extensive vitiligo. Monobenzone is a monobenzyl ether of hydroquinone that undergoes oxidation in melanocytes, generating reactive products that contribute to melanocyte damage and immune-mediated destruction. Unlike conventional skin-lightening agents, it can cause long-lasting or irreversible depigmentation, including at sites distant from application. It is not intended for cosmetic treatment of ordinary hyperpigmentation

CAS Number: 103-16-2

Molecular Mass: 200.23 g/mol

Formula: C₁₃H₁₂O₂

Smiles: Oc1ccc(OCc2ccccc2)cc1

Synonymes:

Monobenzone, 103-16-2, 4-(Benzyloxy)phenol, Hydroquinone monobenzyl ether, Benoquin, P-(BENZYLOXY)PHENOL, Benzoquin, Leucodinine, Monobenzon, Monobenzyl hydroquinone, Superlite, Agerite alba, 4-(Phenylmethoxy)phenol, Hydroquinone benzyl ether, Dermochinona, Carmifal, Depigman, Pigmex, p-Hydroxyphenyl benzyl ether, Alba-Dome, 4-(Benzyloxyl)phenol, Benzyl p-hydroxyphenyl ether, Monobenzyl ether hydroquinone, Phenol, 4-(phenylmethoxy)-, Monobenzona, Monobenzonum, Superlite (antioxidant), Benzylhydroquinone, Hydrochinon monobenzylether, P-BENZYLOXYPHENOL, Monobenzyl Ether of Hydroquinone, 4-Benzyloxy-phenol, NSC-2132, 9L2KA76MG5, DTXSID2020717, CHEBI:34380, DTXCID00717, NSC33918, RefChem:55663, D11AX13, 203-083-3, 4-Benzyloxyphenol, Benzyl hydroquinone, 4-phenylmethoxyphenol, Monobenzone [INN], Alba, Monobenzonum [INN-Latin], Monobenzona [INN-Spanish], Hydrochinon monobenzylether [Czech], MFCD00002333, Phenol, p-(benzyloxy)-, 4-phenylmethoxy-phenol, NSC 2132, Monobenzone (Benoquin), 4-benzyloxy phenol, NCGC00016360-01, CAS-103-16-2, WLN: QR DO1R, Benoquin (TN), HSDB 4019, SR-05000001819, Monobenzone (USP/INN), Monobenzone [USP:INN], EINECS 203-083-3, BRN 1958305, UNII-9L2KA76MG5, 4-benzoxyphenol, AI3-14325, Hydroquinone Monobenzylether, 4-Benzyloxyphenol, 4-(Benzyloxy)phenol, 4-benzyloxylphenol, p-benzyloxy phenol, p-benzyloxy-phenol, 4(benzyloxy)phenol, (p)-Benzyloxyphenol, 4-(benzyloxy)-phenol, para-(Benzyloxy)phenol, Monobenzone (Standard), MONOBENZONE [MI], Prestwick0_000912, Prestwick1_000912, Prestwick2_000912, Prestwick3_000912, MONOBENZONE [HSDB], MONOBENZONE [VANDF], CHEMBL1388, MONOBENZONE [MART.], Epitope ID:1309333, Oprea1_698781, SCHEMBL35631, BSPBio_000784, MONOBENZONE [USP-RS], MONOBENZONE [WHO-DD], 4-(Benzyloxy)phenol, 98%, 4-06-00-05728 (Beilstein Handbook Reference), BIDD:ER0003, SPBio_002973, BPBio1_000864, GTPL6830, orb1310317, orb3025310, SCHEMBL2095112, SCHEMBL9278742, SCHEMBL10414960, SCHEMBL27834150, 4-(Benzyloxy)phenol, >=99%, MONOBENZONE [ORANGE BOOK], NSC2132, HMS1570H06, HMS1580P12, HMS2097H06, HMS3655K15, HMS3714H06, HMS5079P06, Pharmakon1600-01503031, MONOBENZONE [USP MONOGRAPH], CS-B0870, Tox21_110396, Tox21_201147, 4-(Benzyloxy)phenol, Hydroquinone monobenzyl ether, PBP, Monobenzone, BDBM50410520, EBC-04128, HY-30272R, NSC-33918, NSC758211, s1652, SBB038524, STL283939, AKOS000119555, Tox21_110396_1, AC-2492, CCG-213094, DB00600, FH02681, NSC-758211, PS-8213, NCGC00016360-02, NCGC00016360-03, NCGC00016360-05, NCGC00016360-06, NCGC00258699-01, FH178558, HY-30272, SY001650, AB00513959, NS00001735, ST50170917, SW197310-3, EN300-20495, D05072, F11201, AB00513959-03, AB00513959_04, AB00513959_05, F078490, Q2768526, SR-05000001819-1, SR-05000001819-2, SR-05000001819-3, BRD-K54262262-001-01-7, BRD-K54262262-001-06-6, BRD-K54262262-001-09-0, BRD-K54262262-001-10-8, BRD-K54262262-001-11-6, BRD-K54262262-001-12-4, F0777-0782, Z104478412, Monobenzone, United States Pharmacopeia (USP) Reference Standard, 4-(Benzyloxy)phenol , Hydroquinone monobenzyl ether , PBP , Monobenzone

Bioactivity: Depigmenting agent; melanocytotoxic hydroquinone derivative that induces melanocyte destruction

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1,4-Dioxane	288.15	-	234.6	[116]
1,4-Dioxane	293.15	-	355.0	[116]
1,4-Dioxane	298.15	-	548.0	[116]
1,4-Dioxane	303.15	-	808.8	[116]
1,4-Dioxane	308.15	-	1200.2	[116]
1,4-Dioxane	313.15	-	1769.0	[116]
1-Butanol	283.15	-	51.37	[116]
1-Butanol	288.15	-	63.72	[116]
1-Butanol	293.15	-	78.41	[116]
1-Butanol	298.15	-	98.69	[116]
1-Butanol	303.15	-	124.4	[116]
1-Butanol	308.15	-	153.8	[116]
1-Butanol	313.15	-	195.4	[116]
1-Octanol	283.15	-	9.267	[116]
1-Octanol	288.15	-	12.96	[116]
1-Octanol	293.15	-	17.45	[116]
1-Octanol	298.15	-	21.96	[116]
1-Octanol	303.15	-	28.86	[116]
1-Octanol	308.15	-	37.2	[116]
1-Octanol	313.15	-	45.85	[116]
1-Propanol	283.15	-	107.1	[115]
1-Propanol	283.15	-	79.93	[116]
1-Propanol	288.15	-	125.5	[115]
1-Propanol	288.15	-	98.13	[116]
1-Propanol	293.15	-	146.7	[115]
1-Propanol	293.15	-	119.7	[116]
1-Propanol	298.15	-	171.7	[115]
1-Propanol	298.15	-	146.5	[116]
1-Propanol	303.15	-	200.2	[115]
1-Propanol	303.15	-	181.9	[116]
1-Propanol	308.15	-	230.7	[115]
1-Propanol	308.15	-	227.5	[116]
1-Propanol	313.15	-	269.3	[115]
1-Propanol	313.15	-	289.6	[116]
1-Propanol	318.15	-	308.5	[115]
1-Propanol	323.15	-	353.0	[115]
1-Propanol	328.15	-	409.6	[115]
Acetone	283.15	-	0.047	[116]
Acetone	288.15	-	0.055	[116]
Acetone	293.15	-	0.0627	[116]
Acetone	298.15	-	0.0731	[116]
Acetone	303.15	-	0.0833	[116]
Acetone	308.15	-	0.0933	[116]
Acetone	313.15	-	0.11	[116]
Acetonitrile	283.15	-	145.0	[116]
Acetonitrile	288.15	-	179.7	[116]
Acetonitrile	293.15	-	220.4	[116]
Acetonitrile	298.15	-	271.6	[116]
Acetonitrile	303.15	-	336.4	[116]
Acetonitrile	308.15	-	419.2	[116]
Acetonitrile	313.15	-	528.4	[116]
Cyclohexane	283.15	-	1.016	[116]
Cyclohexane	288.15	-	1.74	[116]
Cyclohexane	293.15	-	2.891	[116]
Cyclohexane	298.15	-	4.819	[116]
Cyclohexane	303.15	-	7.276	[116]
Cyclohexane	308.15	-	10.6	[116]
Cyclohexane	313.15	-	14.61	[116]
Dimethylformamide	283.15	-	0.147	[116]
Dimethylformamide	288.15	-	0.162	[116]
Dimethylformamide	293.15	-	0.179	[116]
Dimethylformamide	298.15	-	0.202	[116]
Dimethylformamide	303.15	-	0.226	[116]
Dimethylformamide	308.15	-	0.26	[116]
Dimethylformamide	313.15	-	0.2928	[116]
Ethanol	283.15	-	175.9	[115]
Ethanol	283.15	-	114.1	[116]
Ethanol	288.15	-	204.5	[115]
Ethanol	288.15	-	142.2	[116]
Ethanol	293.15	-	236.1	[115]
Ethanol	293.15	-	174.4	[116]
Ethanol	298.15	-	271.6	[115]
Ethanol	298.15	-	215.8	[116]
Ethanol	303.15	-	313.7	[115]
Ethanol	303.15	-	269.4	[116]
Ethanol	308.15	-	356.7	[115]
Ethanol	308.15	-	335.7	[116]
Ethanol	313.15	-	409.7	[115]
Ethanol	313.15	-	418.6	[116]
Ethanol	318.15	-	466.6	[115]
Ethanol	323.15	-	525.2	[115]
Ethanol	328.15	-	603.0	[115]
Ethyl acetate	283.15	-	173.8	[116]
Ethyl acetate	288.15	-	306.2	[116]
Ethyl acetate	293.15	-	514.8	[116]
Ethyl acetate	298.15	-	842.4	[116]
Ethyl acetate	303.15	-	1342.6	[116]
Ethyl acetate	308.15	-	2167.6	[116]
Ethyl acetate	313.15	-	3412.7	[116]
Ethylene Glycol	283.15	-	19.26	[115]
Ethylene Glycol	288.15	-	24.1	[115]
Ethylene Glycol	293.15	-	29.75	[115]
Ethylene Glycol	298.15	-	36.38	[115]
Ethylene Glycol	303.15	-	45.06	[115]
Ethylene Glycol	308.15	-	53.92	[115]
Ethylene Glycol	313.15	-	64.92	[115]
Ethylene Glycol	318.15	-	78.21	[115]
Ethylene Glycol	323.15	-	92.93	[115]
Ethylene Glycol	328.15	-	109.2	[115]
Hexane	283.15	-	0.508	[116]
Hexane	288.15	-	0.6991	[116]
Hexane	293.15	-	1.148	[116]
Hexane	298.15	-	1.642	[116]
Hexane	303.15	-	2.43	[116]
Hexane	308.15	-	3.403	[116]
Hexane	313.15	-	4.681	[116]
Isopropanol	283.15	-	58.65	[115]
Isopropanol	283.15	-	86.53	[116]
Isopropanol	288.15	-	70.51	[115]
Isopropanol	288.15	-	104.8	[116]
Isopropanol	293.15	-	83.12	[115]
Isopropanol	293.15	-	130.9	[116]
Isopropanol	298.15	-	98.56	[115]
Isopropanol	298.15	-	161.6	[116]
Isopropanol	303.15	-	114.9	[115]
Isopropanol	303.15	-	205.6	[116]
Isopropanol	308.15	-	136.3	[115]
Isopropanol	308.15	-	261.3	[116]
Isopropanol	313.15	-	158.4	[115]
Isopropanol	313.15	-	336.8	[116]
Isopropanol	318.15	-	183.0	[115]
Isopropanol	323.15	-	213.4	[115]
Isopropanol	328.15	-	247.4	[115]
Methanol	283.15	-	197.9	[116]
Methanol	288.15	-	248.5	[116]
Methanol	293.15	-	311.5	[116]
Methanol	298.15	-	392.1	[116]
Methanol	303.15	-	487.6	[116]
Methanol	308.15	-	607.4	[116]
Methanol	313.15	-	757.0	[116]
N-Methyl-2-pyrrolidone	283.15	-	0.3199	[116]
N-Methyl-2-pyrrolidone	288.15	-	0.3332	[116]
N-Methyl-2-pyrrolidone	293.15	-	0.3465	[116]
N-Methyl-2-pyrrolidone	298.15	-	0.3657	[116]
N-Methyl-2-pyrrolidone	303.15	-	0.3994	[116]
N-Methyl-2-pyrrolidone	308.15	-	0.4387	[116]
N-Methyl-2-pyrrolidone	313.15	-	0.4862	[116]
Water	283.15	-	0.0397	[115]
Water	283.15	-	0.056	[116]
Water	288.15	-	0.0498	[115]
Water	288.15	-	0.078	[116]
Water	293.15	-	0.0626	[115]
Water	293.15	-	0.1	[116]
Water	298.15	-	0.078	[115]
Water	298.15	-	0.144	[116]
Water	303.15	-	0.0964	[115]
Water	303.15	-	0.188	[116]
Water	308.15	-	0.1179	[115]
Water	308.15	-	0.254	[116]
Water	313.15	-	0.143	[115]
Water	313.15	-	0.33	[116]
Water	318.15	-	0.1732	[115]
Water	323.15	-	0.2094	[115]
Water	328.15	-	0.2511	[115]

Molecule 3D descriptors

Descriptor	Value
PMI1	202.4429
PMI2	2364.4863
PMI3	2386.2907
NPR1	0.0848
NPR2	0.9909
RadiusOfGyration	3.5169
InertialShapeFactor	0.0049
Eccentricity	0.9964
Asphericity	0.7699
SpherocityIndex	0.2010
PBF	0.5639