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Home > Encyclopedia > Monobenzone

Monobenzone

pharmaceutical raw materials
Monobenzone structure

Monobenzone 

structure
  • CAS No:

    103-16-2

  • Formula:

    C13H12O2

  • Chemical Name:

    Monobenzone

  • Synonyms:

    Phenol,4-(phenylmethoxy)-;Phenol,p-(benzyloxy)-;4-(Phenylmethoxy)phenol;Alba-Dome;Benoquin;Hydroquinone benzyl ether;Hydroquinone monobenzyl ether;p-Hydroxyphenyl benzyl ether;Monobenzone;Monobenzyl ether hydroquinone;Monobenzyl hydroquinone;AgeRite Alba;Superlite (antioxidant);p-(Benzyloxy)phenol;4-(Benzyloxy)phenol;Benzyl p-hydroxyphenyl ether;Monobenzon;Benzoquin;Carmifal;Depigman;Dermochinona;Leucodinine;Pigmex;Superlite;Agerite;NSC 2132;NSC 33918

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Solid


Solid


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.|Monobenzone is the monobenzyl ether of hydroquinone used medically for depigmentation. Monobenzone occurs as a white, almost tasteless crystalline powder, soluble in alcohol and practically insoluble in water. It exerts a depigmenting effect on skin of mammals by increasing the excretion of melanin from the melanocytes. It may also cause destruction of melanocytes and permanent depigmentation.|Monobenzone is a Depigmenting Agent. The mechanism of action of monobenzone is as a Melanin Synthesis Inhibitor. The physiologic effect of monobenzone is by means of Depigmenting Activity.|Monobenzone is a monobenzyl ether of hydroquinone with topical depigmentation activity. Although the exact mechanism of action of depigmentation is unknown, the metabolites of monobenzone appear to have a cytotoxic effect on melanocytes. Furthermore, the depigmentation effect might be mediated through the inhibition of tyrosinase, which is essential in the synthesis of melanin pigments, thereby causing permanent depigmentation of the skin.

Monobenzone Basic Attributes

200.237

200.23

203-083-3

9L2KA76MG5

758211|33918|2132

DTXSID2020717

C992

LUSTROUS LEAFLETS FROM WATER|WHITE CRYSTALLINE POWDER

D - Dermatologicals

29095090

Characteristics

29.5

3.4

Solid

1.26 g/cm3

122.5 °C

359.1ºC at 760mmHg

213.4ºC

3.92e-02 g/L

Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

ODORLESS

Safety Information

I; II; III

2

R36; R43

S24/25-S26-S37

SJ7700000

Xi

Stable under normal temperatures and pressures.

P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, P501

H317

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 141 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified

Toxicity

LD50 Rat oral >3.2 g/kg /Hydroquinone monobenzyl ether (Sodium salt/

IN RUBBER INDUSTRY, NUMBER OF CHEMICAL AGENTS USED IN PREPARING RUBBER CAN SENSITIZE EXPOSED WORKERS. THESE INCL...ANTIOXIDANT, MONOBENZYL ETHER OF HYDROQUINONE...

Drug Information

Used topically to treat the loss of skin color (vitiligo).|FDA Label

MONOBENZONE, MONOBENZYL ETHER OF HYDROQUINONE, IS AMELANOTIC AGENT USED IN SEVERE FRECKLING & OTHER CONDITIONS CHARACTERIZED BY HYPERPIGMENTATION OF SKIN.|IT IS APPLIED TO HYPERPIGMENTED AREAS 2 OR 3 TIMES DAILY FOR UP TO 4 MO, OR UNTIL DEPIGMENTATION HAS OCCURRED, & THEN TWICE WEEKLY TO MAINTAIN EFFECT. ... IF SATISFACTORY RESPONSE IS NOT OBSERVED WITHIN 4 MO, TREATMENT SHOULD BE DISCONTINUED.|...POSSIBLY EFFECTIVE FOR TREATMENT OF HYPERPIGMENTATION CAUSED BY EXCESSIVE FORMATION OF MELANIN, SUCH AS OCCURS IN GENERALIZED LENTIGO...MELASMA OF PREGNANCY, & HYPERPIGMENTATION FOLLOWING INFLAMMATION OF SKIN.|VITILIGO PATIENTS USED 20% MONOBENZONE 2 TIMES/DAY UNTIL DEPIGMENTATION; THOSE ACHIEVING COMPLETE DEPIGMENTATION WERE TREATED FOR 10 MO OR MORE. DEPIGMENTATION INDUCED BY MONOBENZONE IS GENERALLY IRREVERSIBLE.|For more Therapeutic Uses (Complete) data for P-(BENZYLOXY)PHENOL (6 total), please visit the HSDB record page.

TREATED AREAS SHOULD NOT BE EXPOSED TO SUNLIGHT; ULTRAVIOLET LIGHT NEUTRALIZES DEPIGMENTING EFFECT.|MONOBENZONE THERAPY IS OFTEN DIFFICULT TO MANAGE & REQUIRES CAREFUL PT FOLLOW-UP; IT CAN PRODUCE BIZARRE PATTERNS, WITH HYPOPIGMENTATION @ SITES DISTANT FROM AREA OF APPLICATION.|...SHOULD ONLY BE USED TO PERMANENTLY REMOVE REMAINING AREAS OF NORMAL PIGMENTATION IN PT WITH DISSEMINATED VITILIGO. ...NOT RECOMMENDED IN TREATMENT OF MELASMA OR POSTINFLAMMATORY & OTHER TYPES OF HYPERPIGMENTATION. ...MAY CAUSE HYPERSENSITIVITY REACTIONS.|SINCE DRUG DOES NOT DESTROY MELANOCYTES OR FACILITATE LOSS OF PREVIOUSLY SYNTHESIZED MELANIN, RESPONSE TO THERAPY IS USUALLY NOT APPARENT UNTIL 1-4 MO. ... UNLESS CAREFULLY APPLIED, UNSIGHTLY DEPIGMENT PATCHES MAY RESULT FROM ITS USE.

Monobenzone is the monobenzyl ether of hydroquinone. Monobenzone, applied topically to the skin, is used as a depigmenting agent inhibitting melanin produced by polymerization of oxidation products of tyrosine and dihydroxyphenyl compounds. Monobenzone works by permanently removing color from normal skin located around skin with vitiligo.

... Predicted by its low chronic toxicity ... hydroquinone monobenzyl ether may readily be metabolized in the same manner as phenol.

Monobenzone is a depigmenting agent whose mechanism of action is not fully understood. It is proposed that it increases the excretion of melanin from the melanocytes. This effect is erratic and may take one to four months to occur while existing melanin is lost with normal sloughing of the stratum corneum. Hyperpigmented skin appears to fade more rapidly than does normal skin, and exposure to sunlight reduces the depigmenting effect of the drug. Following skin depigmentation after topical application of monobenzone, the histological studies indicate similar results as that seen in vitiligo, where the epidermis is intact but with the absence of identifiable melanocytes.|...INTERFERES WITH BIOSYNTHESIS OF MELANIN. IT INHIBITS ENZYME TYROSINASE & THEREBY PREVENTS CONVERSION OF TYROSINE TO DIHYDROXYPHENYLALANINE, PRECURSOR OF MELANIN.

UNTOWARD EFFECTS, INCL MILD ERYTHEMA, DERMATITIS, & ECZEMATOUS REACTIONS, HAVE BEEN REPORTED. ... SYSTEMIC TOXICITY HAS NOT BEEN OBSERVED AFTER ITS LOCAL APPLICATION.|SUMMARY TOXICITY STATEMENT: ACUTE... LOW... LOW= CAUSES READILY REVERSIBLE TISSUE CHANGES WHICH DISAPPEAR AFTER EXPOSURE STOPS; CAUSES SOME DISCOMFORT.|... Many cases of dermatitis and leucoderma that were evidently caused by skin contact with rubber that contained hydroquinone monobenzyl ether as an antioxidant /have been reported/.

agerite alba

Monobenzone Use and Manufacturing

Methods of Manufacturing

REACTION OF SODIUM PHENOXIDE WITH BENZYL CHLORIDE; REACTION OF HYDROQUINONE AND BENZYL BROMIDE IN ALCOHOLIC POTASSIUM HYDROXIDE|PREPD IN VARIOUS WAYS. ONE METHOD INVOLVES CONDENSING SODIUM P-NITROPHENOLATE WITH BENZYL CHLORIDE TO PRODUCE BENZYL P-NITROPHENYL ETHER FOLLOWED BY 1) REDUCTION OF NITRO TO AMINO, 2) DIAZOTIZATION OF AMINO, & 3) HYDROLYTIC DECOMP OF DIAZONIUM CMPD TO CORRESPONDING PHENOL.

Uses

Antioxidant for paraffins and polyvinyl chloride, polypropylene and polypropylene oxide, chemical intermediate in organic synthesis.

Production

(1974) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

IT IS MARKETED AS MONOBENZONE LOTION, NF, 5% SOLN IN ISOPROPYL ALCOHOL & PROPYLENE GLYCOL, & MONOBENZONE OINTMENT, NF, WHICH CONTAINS 20% OF ACTIVE INGREDIENT IN SUITABLE BASE.

Phenol, 4-(phenylmethoxy)-: ACTIVE

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:200.23
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:200.083729621
Monoisotopic Mass:200.083729621
Topological Polar Surface Area:29.5
Heavy Atom Count:15
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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