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Monobenzone

CAS No.
103-16-2
Chemical Name:
Monobenzone
Synonyms
MONOBENZONE;HYDROQUINONE MONOBENZYL ETHER;PBP;Monobenzon;Monobenzone powder;Alba;Benoquin;Benzoquin;oxyphenoL;P-BENZYLOXYPHENOL
CBNumber:
CB2156828
Molecular Formula:
C13H12O2
Molecular Weight:
200.23
MDL Number:
MFCD00002333
MOL File:
103-16-2.mol
MSDS File:
SDS
Last updated:2024-12-18 14:07:02

Monobenzone Properties

Melting point 119-120 °C (lit.)
Boiling point 297.96°C (rough estimate)
Density 1,26 g/cm3
refractive index 1.5906 (estimate)
storage temp. Store below +30°C.
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka 10.29±0.15(Predicted)
form Powder, Crystals, and/or Chunks
color Off-white to beige to brown
Water Solubility slightly soluble
Merck 14,6248
BRN 1958305
InChIKey VYQNWZOUAUKGHI-UHFFFAOYSA-N
LogP 2.651 (est)
Indirect Additives used in Food Contact Substances HYDROQUINONE MONOBENZYL ETHER
FDA 21 CFR 175.105; 177.2600
CAS DataBase Reference 103-16-2(CAS DataBase Reference)
FDA UNII 9L2KA76MG5
NCI Drug Dictionary Benoquin
ATC code D11AX13
NIST Chemistry Reference Monobenzone(103-16-2)
EPA Substance Registry System Monobenzone (103-16-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H317-H319
Precautionary statements  P280-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36-43
Safety Statements  24/25-26-37
WGK Germany  2
RTECS  SJ7700000
Hazard Note  Irritant
TSCA  Yes
HS Code  29095090
Hazardous Substances Data 103-16-2(Hazardous Substances Data)
Toxicity LD50 i.p. in mice: >600 mg/kg (Takahashi)
NFPA 704
1
2 0

Monobenzone price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SAB4502265 Anti-MED1 antibody produced in rabbit affinity isolated antibody 100μG $506 2024-03-01 Buy
Sigma-Aldrich 158348 4-(Benzyloxy)phenol 98% 103-16-2 25g $49.9 2024-03-01 Buy
Sigma-Aldrich PHR3208 Monobenzone pharmaceutical secondary standard, certified reference material 103-16-2 500MG $139 2024-03-01 Buy
Sigma-Aldrich 1445506 Monobenzone United States Pharmacopeia (USP) Reference Standard 103-16-2 200mg $436 2024-03-01 Buy
TCI Chemical B1104 4-(Benzyloxy)phenol >99.0%(GC) 103-16-2 25g $39 2024-03-01 Buy
Product number Packaging Price Buy
SAB4502265 100μG $506 Buy
158348 25g $49.9 Buy
PHR3208 500MG $139 Buy
1445506 200mg $436 Buy
B1104 25g $39 Buy

Monobenzone Chemical Properties,Uses,Production

Description

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.

Chemical Properties

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.

Uses

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

Uses

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.

Uses

PBP is used as antiinflammatory, antisecretory, antiulcer.

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.

Preparation

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%.

brand name

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

Biological Activity

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].

Side effects

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.

Purification Methods

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.]

References

[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.

146631-00-7
103-16-2
Synthesis of Monobenzone from 4-Benzyloxybenzeneboronic acid
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View Lastest Price from Monobenzone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Monobenzone pictures 2024-12-23 Monobenzone
103-16-2
US $0.00 / Kg/Drum 1KG 99% 100mt Jinan Finer Chemical Co., Ltd
PBP pictures 2024-12-23 PBP
103-16-2
US $6.00 / kg 1kg 99% 2000KG/Month HebeiShuoshengImportandExportco.,Ltd
Monobenzone pictures 2024-12-23 Monobenzone
103-16-2
US $100.00-80.00 / kg 1kg 99% 5000kg/ week Hebei Zhuanglai Chemical Trading Co.,Ltd
  • Monobenzone pictures
  • Monobenzone
    103-16-2
  • US $0.00 / Kg/Drum
  • 99%
  • Jinan Finer Chemical Co., Ltd
  • PBP pictures
  • PBP
    103-16-2
  • US $6.00 / kg
  • 99%
  • HebeiShuoshengImportandExportco.,Ltd
  • Monobenzone pictures
  • Monobenzone
    103-16-2
  • US $100.00-80.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
BENZYL P-HYDROXYPHENYL ETHER P-HYDROXYPHENYL BENZYL ETHER 4-BENZYLOXYPHENOL AKOS BBS-00000682 4-(BENZYLOXY)PHENOL, 99+% 4-Benzyloxyphenol, 98+% p-Benzyloxyphenone BENZYL HYDOQUINONE 4-benzyloxylphenol 4-BENZYLOXY PHENOL (MONO-BENZONE) 4-BENZYLOXY PHENOL (MONO-BENZONE) USP GRADE 4-BENZYLOXYPHENOL, 98.5+% MONOBENZONE(4-PHENYLMETHOXYPHENOL) benzyloxy phenol (monobenzone) MONOBENZONE CREAM5%-30% 4-(BENZYLOXY)IPHENOL monobenzone 4-hydroxyphenyl benzyl ether hydroquinone monobenzyl ether Monobenzone (200 mg) HYDROQUINONE MONOBENZYL ETHER, N F Monobenzone, USP 4-Benzyloxyphenol,4-(Benzyloxy)phenol Monobenzone creaM Enzoquin 4-Benzyloxyphenol (Monobenzone USP) 4-(phenylmethoxy)-pheno 4-(Phenylmethoxy)phenol monobenzyletherhydroquinone monobenzylhydroquinone p-(benzyloxy)-pheno para-(Benzyloxy)phenol Phenol, 4-(phenylmethoxy)- Phenol, p-(benzyloxy)- Phenol,4-(phenylmethoxy)- Pigmex Superlite superlite(antioxidant) 4-Benzyloxyphenol, 98% 50GR 4 - phenol Mono with benzene 4-(Benzyloxy)p Anti-MED1 antibody produced in rabbit Mediator complex subunit 1 PPAR-binding protein Thyroid hormone receptor-associated protein complex 220 kDa component Neuropolypeptide h3 ANTI-PBP (CENTER) antibody produced in rabbit ANTI-PBP antibody produced in mouse PEBP RKIP ANTI-PBP(N-TERMINAL) antibody produced in rabbit HCNPpp PEBP1 Phosphatidylethanolamine-binding protein 1 Agerite Agerite alba ageritealba Alba-dome Carmifal