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Monobenzone

Product Name
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
Formula Weight
200.23
MOL File
103-16-2.mol
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Monobenzone Property

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)
CAS DataBase Reference
103-16-2(CAS DataBase Reference)
NIST Chemistry Reference
Monobenzone(103-16-2)
EPA Substance Registry System
Monobenzone (103-16-2)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

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

PBP is used as antiinflammatory, antisecretory, antiulcer.

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.

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%.

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.

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.

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.

Monobenzone Preparation Products And Raw materials

Raw materials

Preparation Products

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Monobenzone Suppliers

TCI Europe
Tel
320-37350700
Fax
+32 (0)37350701
Email
sales@tcieurope.eu
Country
Europe
ProdList
23671
Advantage
75
ecochem international chemical broker
Tel
--
Fax
--
Email
export@ecochem.dk
Country
Europe
ProdList
6371
Advantage
66
kemikalieimport
Tel
--
Fax
--
Email
Sales@kemikalieimport.dk
Country
Europe
ProdList
6685
Advantage
47
Nantong Chem-Tech.(Group) Co., Ltd
Tel
--
Fax
--
Email
ni.trade@pub.nt.jsinfo.net
Country
Europe
ProdList
1811
Advantage
56
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View Lastest Price from Monobenzone manufacturers

Jinan Finer Chemical Co., Ltd
Product
Monobenzone 103-16-2
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
100mt
Release date
2021-11-17
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Monobenzone 103-16-2
Price
US $100.00-80.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/ week
Release date
2024-04-23
HebeiShuoshengImportandExportco.,Ltd
Product
PBP 103-16-2
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-02

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