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하이드로퀴논모노벤질에터

Monobenzone

HCID 7638
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
103-16-2
표준 SMILES
Oc1ccc(OCc2ccccc2)cc1
InChIKey
VYQNWZOUAUKGHI-UHFFFAOYSA-N
분자식
C13H12O2
평균 분자량
200.23 g/mol
단동위원소 질량
200.08372962

개요

Monobenzone is the monobenzyl ether of hydroquinone. It is used as a topical drug for medical depigmentation. It has a role as a dermatologic drug, an allergen and a melanin synthesis inhibitor. It is functionally related to a hydroquinone.

이름 및 식별자

우선 이름
Monobenzone
IUPAC
4-phenylmethoxyphenol
현지명
하이드로퀴논모노벤질에터
영어명
Monobenzone
분자식
C13H12O2
분자량
200.23

이름 및 동의어

Monobenzone103-16-24-(Benzyloxy)phenolHydroquinone monobenzyl etherBenoquinP-(BENZYLOXY)PHENOLBenzoquinDepigmanLeucodinineMonobenzonMonobenzyl hydroquinoneSuperlite
이름 더 보기
하이드로퀴논모노벤질에터PBPMonobenzone powder4-BENZYLOXYPHENOLAlbaP-BENZYLOXYPHENOLBenzyl hydroquinone
PigmexAgerite alba4-(Phenylmethoxy)phenol4-(Benzyloxyl)phenolHydroquinone benzyl etherDermochinonaCarmifalp-Hydroxyphenyl benzyl ether

데이터베이스 식별자

CAS
103-16-2
PubChem CID
7638
DTXSID
DTXSID2020717
ChEMBL
CHEMBL1388
ChEBI
CHEBI:34380
UNII
9L2KA76MG5
EC Number
203-083-3
Nikkaji
J5.012A

물성

구조 계산 물성

XLogP
3.4
극성 표면적
29.5 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
3
무거운 원자 수
15
형식 전하
0
복잡도
167

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Other Aromatic Compounds
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesChemical diffusion
LogP3.2
OdorODORLESS
Density1.26
Color/Form · 2건

LUSTROUS LEAFLETS FROM WATER

WHITE CRYSTALLINE POWDER

Solubility · 5건

SOLUBILITY IN BOILNG WATER ABOUT 1.0 G/100 ML; SOL IN ALC, ETHER, BENZENE

INSOL IN WATER

FREELY SOL IN ACETONE

Practically insoluble in petroleum hydrocarbons, very soluble in benzene and alkalies.

3.92e-02 g/L

Human Drugs · 2건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory InformationChemical: Phenol, 4-(phenylmethoxy)-
Hazards Summary · 1건

A tumorigen and mild skin irritant; Intraperitoneal LD50 (rat) = 4500 mg/kg; [RTECS] Emergency treatment: symptomatic chemical dermal exposure; Reported skin sensitizer in the rubber industry; [HSDB] An eye irritant; May cause skin sensitization; [ESIS] A strong eye irritant; May cause skin sensitization; [Alfa Aesar MSDS]

Hazard Classes and Categories · 3건

Skin Sens. 1 (100%)

Eye irritation - category 2

Eye Irrit. 2

안전 및 보호

Disposal Methods · 1건

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.

독성 정보

화학 및 산업

약리 정보

ATC Code · 2건

D - Dermatologicals

QD - Dermatologicals

Pharmacodynamics · 1건

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.

Mechanism of Action · 2건

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.

Metabolism/Metabolites... Predicted by its low chronic toxicity ... hydroquinone monobenzyl ether may readily be metabolized in the same manner as phenol.
FDA Pharmacological Classification · 6건

9L2KA76MG5

MONOBENZONE

Physiologic Effects [PE] - Depigmenting Activity

Established Pharmacologic Class [EPC] - Depigmenting Agent

Mechanisms of Action [MoA] - Melanin Synthesis Inhibitors

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.

Cellular LocationsCytoplasm

관련 반응

338건
반응 기록 만들기
HRID 992 반응식
HRID 992반응물로uspto-grants-1998_03
HRID 1520 반응식
HRID 1520반응물로uspto-grants-1998_03
HRID 9255 반응식
HRID 9255반응물로uspto-grants-2006_08
HRID 12922 반응식
HRID 12922반응물로uspto-grants-2010_06
HRID 33814 반응식
HRID 33814반응물로uspto-grants-2008_09
HRID 34701 반응식
HRID 34701반응물로uspto-grants-1988_08
HRID 51077 반응식
HRID 51077반응물로uspto-grants-2004_03
HRID 64581 반응식
HRID 64581반응물로uspto-grants-1986_09
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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새 노트새 반응견적 요청하기
· 2건

122.5 °C

110 - 118 °C

Vapor Pressure0.0000225 [mmHg]

물리화학적 성질

녹는점
119 · 119-120 °C (lit.)
끓는 점
297.96 °C · 297.96°C (rough estimate)
밀도
1 · 1,26 g/cm3
굴절률
1.5906 · 1.5906 (estimate)
저장 조건
30 °C · Store below +30°C.
용해도
클로로포름(약간 용해됨), DMSO(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa)
10.29 · 10.29±0.15(Predicted)
물리적 상태
분말, 결정 및/또는 덩어리
색상
미색부터 베이지, 브라운까지
생물학적 소스
rabbit
수용성
약간 용해됨
Merck
14 · 14,6248
BRN
1958305 · 1958305
InChI
1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2
InChIKey
VYQNWZOUAUKGHI-UHFFFAOYSA-N
SMILES
Oc1ccc(OCc2ccccc2)cc1
LogP
2.651 · 2.651 (est)
NIST
Monobenzone(103-16-2)
EPA
Monobenzone (103-16-2)
화학적 성질 · 1건

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.

Adverse Effects
Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
Human Toxicity Excerpts · 3건

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/.

Non-Human Toxicity Excerpts · 3건

... No toxic changes were observed in guinea pigs ingesting this compound at the level of 160 mg/kg daily for 2 months for a total dose of 4.37 g. The only change noted was a depigmentation of the hair.

... No toxic changes were observed in mice that were injected ip with 600 mg/kg of hydroquinone monobenzyl ether daily for 3 weeks.

... A 5 percent concentration of hydroquinone monobenzyl ether in ethanol ... was nonsensitizing /to guinea pigs/.

Probable Routes of Human ExposureIN RUBBER INDUSTRY, NUMBER OF CHEMICAL AGENTS USED IN PREPARING RUBBER CAN SENSITIZE EXPOSED WORKERS. THESE INCL...ANTIOXIDANT, MONOBENZYL ETHER OF HYDROQUINONE...
Non-Human Toxicity ValuesLD50 Rat oral >3.2 g/kg /Hydroquinone monobenzyl ether (Sodium salt/

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
SJ7700000
독성
LD50 i.p. in mice: >600 mg/kg (Takahashi)
HS 번호
29095090
risk_code
36-43
hazard_code
Xi
safety_code
24/25-26-37
위험 참고 사항
Irritant
Hazard Classifications
Eye Irrit. 2Skin Sens. 1
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
103-16-2(Hazardous Substances Data)

용도 및 제조

Uses · 5건

Used as a solvent and in perfumes, soap, plastics, and pharmaceuticals; [Hawley] Used as an antioxidant (rubber, paraffins, and polyvinyl chloride), stabilizer, polymerization inhibitor, intermediate, and depigmentor to treat hyperpigmentation of the skin; [HSDB]

ANTIOXIDANT FOR PARAFFINS AND POLYVINYL CHLORIDE, POLYPROPYLENE AND POLYPROPYLENE OXIDE; CHEM INT IN ORGANIC SYNTHESIS

Rubber antioxidant, stabilizer, polymerization inhibitor, chemical intermediate.

MEDICATION

MEDICATION (VET)

U.S. Production · 2건

(1974) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 2건

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.

Formulations/PreparationsIT 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.
General Manufacturing InformationPhenol, 4-(phenylmethoxy)-: ACTIVE
응용 분야 · 2건

개요4-(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.

용도4-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.

제조 방법 · 1건

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%.

상·하류 제품 정보

상류 원료

1,4-Dibenzyloxybenzene염화벤질벤질브로마이드하이드로퀴논

하류 제품

3,5-디오도티로아세트산벤질페닐에테르Benzyl tiglateCesium hydroxide1-(벤질옥시)-4-(3-클로로프로폭시)벤젠Octadecanoic acid,4-(phenylmethoxy)phenyl ester

추가 설명

정의ChEBI: 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.