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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O2
Molecular Weight 110.1106
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Hydroquinone

SMILES

OC1=CC=C(O)C=C1

InChI

InChIKey=QIGBRXMKCJKVMJ-UHFFFAOYSA-N
InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H

HIDE SMILES / InChI

Molecular Formula C6H6O2
Molecular Weight 110.1106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Hydroquinone

Hydroquinone, aka benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. Its chemical structure features two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843. In human medicine, hydroquinone is used as a topical application in skin whitening to reduce the color of skin. It does not have the same predisposition to cause dermatitis as metol does. In 2006, the United States Food and Drug Administration revoked its previous approval of hydroquinone and proposed a ban on all over-the-counter preparations. The FDA stated that hydroquinone cannot be ruled out as a potential carcinogen. This conclusion was reached based on the extent of absorption in humans and the incidence of neoplasms in rats in several studies where adult rats were found to have increased rates of tumours, including thyroid follicular cell hyperplasias, anisokaryosis (variation in nuclei sizes), mononuclear cell leukemia, hepatocellular adenomas and renal tubule cell adenomas. One of the components in TRI-LUMA Cream, hydroquinone, is a depigmenting agent, and may interrupt one or more steps in the tyrosine-tyrosinase pathway of melanin synthesis. However, the mechanism of action of the active ingredients in TRI-LUMA Cream in the treatment of melasma is unknown.

Originator

Curator's Comment: Friedrich Wöhler in 1843

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRI-LUMA

Approved Use

TRI-LUMA Cream is indicated for the short-term treatment of moderate to severe melasma of the face, in the presence of measures for sun avoidance, including the use of sunscreens

Launch Date

2002
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
56.035 ng/mL
1 g single, topical
dose: 1 g
route of administration: Topical
experiment type: SINGLE
co-administered: Tretinoin|Fluocinolone
HYDROQUINONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Disc. AE: Application site erythema, Redness facial...
AEs leading to
discontinuation/dose reduction:
Application site erythema
Redness facial
Telangiectasia (grade 3-4)
Rosacea
Facial flushing
Acne
Acne papular
Acne aggravated
Skin irritation
Peeling
Perioral dermatitis
Facial hair increased
Dry skin
Saliva discolouration
Sources:
AEs

AEs

AESignificanceDosePopulation
Acne aggravated Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Acne papular Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Acne Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Application site erythema Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Dry skin Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Facial flushing Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Facial hair increased Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Peeling Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Perioral dermatitis Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Redness facial Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Rosacea Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Saliva discolouration Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Skin irritation Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Telangiectasia grade 3-4
Disc. AE
4 % 1 times / day multiple, topical
Recommended
Dose: 4 %, 1 times / day
Route: topical
Route: multiple
Dose: 4 %, 1 times / day
Sources:
unhealthy, 41.4
Health Status: unhealthy
Age Group: 41.4
Sex: M+F
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Different effects of genistein and resveratrol on oxidative DNA damage in vitro.
2002-01-15
Hepatic and pulmonary microsomal benzene metabolism in CYP2E1 knockout mice.
2001-12-28
Cytochrome P450 isozymes involved in the metabolism of phenol, a benzene metabolite.
2001-12-15
A study on grafting and characterization of HMDI-modified calcium hydrogenphosphate.
2001-12
Release of iron from ferritin by metabolites of benzene and superoxide radical generating agents.
2001-11-30
Alanine-scanning of the 50's loop in the Clostridium beijerinckii flavodoxin: evaluation of additivity and the importance of interactions provided by the main chain in the modulation of the oxidation-reduction potentials.
2001-11-13
Benzene-free synthesis of hydroquinone.
2001-11-07
Total synthesis and determination of the absolute configuration of coscinosulfate. A new selective inhibitor of Cdc25 protein phosphatase.
2001-11-02
Reversal of mitomycin C resistance by overexpression of bioreductive enzymes in Chinese hamster ovary cells.
2001-11-01
GC-MS analysis of hydrophobic root exudates of sorghum and implications on the parasitic plant Striga asiatica.
2001-11
[Effect of C27-steroids on lipid peroxidation in rat liver mitochondria].
2001-10-20
Self-assembly of novel [3]- and [2]rotaxanes with two different ring components: donor-acceptor and hydrogen bonding interactions and molecular-shuttling behavior.
2001-10-19
Photochemistry of methoxyhydroquinone and methoxy-p-benzoquinone in solution related to the photoyellowing of the lignocellulosics.
2001-10
Validated methods for direct determination of hydroquinone glucuronide and sulfate in human urine after oral intake of bearberry leaf extract by capillary zone electrophoresis.
2001-09-25
Validated method for the determination of hydroquinone in human urine by high-performance liquid chromatography-coulometric-array detection.
2001-09-15
Inhibition of DNA cross-linking by mitomycin C by peroxidase-mediated oxidation of mitomycin C hydroquinone.
2001-09-14
Differential involvement of caspases in hydroquinone-induced apoptosis in human leukemic hl-60 and jurkat cells.
2001-09-01
Electrochemical oxidation of ochratoxin A: correlation with 4-chlorophenol.
2001-09
Oxidation of hydroquinones by the versatile ligninolytic peroxidase from Pleurotus eryngii. H2O2 generation and the influence of Mn2+.
2001-09
Structure of an active soluble mutant of the membrane-associated (S)-mandelate dehydrogenase.
2001-08-21
Dual-mode "co-conformational" switching in catenanes incorporating bipyridinium and dialkylammonium recognition sites.
2001-08-17
Mn(III) center availability as a rate controlling factor in the oxidation of phenol and sulfide on delta-MnO2.
2001-08-15
Surface NADH oxidase of HeLa cells lacks intrinsic membrane binding motifs.
2001-08-15
Benzene metabolites antagonize etoposide-stabilized cleavable complexes of DNA topoisomerase IIalpha.
2001-08-01
Concerted action of DT-diaphorase and superoxide dismutase in preventing redox cycling of naphthoquinones: an evaluation.
2001-08
Primary multiple miliary osteoma cutis and exogenous ochronosis.
2001-08
Effect of pre-treatment on the surface and electrochemical properties of screen-printed carbon paste electrodes.
2001-08
Effects of all-trans retinoic acid on melanogenesis in pigmented skin equivalents and monolayer culture of melanocytes.
2001-08
Highly concentrated phenolic wastewater treatment by the photo-Fenton reaction, mechanism study by FTIR-ATR.
2001-08
Protein adducts of 1,4-benzoquinone and benzene oxide among smokers and nonsmokers exposed to benzene in China.
2001-08
Abiotic Fe(III) induced mineralization of phenolic substances.
2001-08
The influence of pH and cadmium sulfide on the photocatalytic degradation of 2-chlorophenol in titanium dioxide suspensions.
2001-08
Role of hydrogen bonding interactions to N(3)H of the flavin mononucleotide cofactor in the modulation of the redox potentials of the Clostridium beijerinckii flavodoxin.
2001-07-31
Inhibitory effect of copper(II) on zinc(II)-induced aggregation of amyloid beta-peptide.
2001-07-27
Strong supramolecular-based magnetic exchange in pi-stacked radicals. Structure and magnetism of a hydrogen-bonded verdazyl radical:hydroquinone molecular solid.
2001-07-25
[Depigmentation for cosmetic purposes: prevalence and side-effects in a female population in Senegal].
2001-07-19
Pharmacokinetic studies in Tg.AC and FVB mice administered [14C] benzene either by oral gavage or intradermal injection.
2001-07-15
Purification and characterization of glutathione conjugate reductase: a component of the tetrachlorohydroquinone reductive dehalogenase system from Phanerochaete chrysosporium.
2001-07-15
Studies on porphyrin-quinhydrone complexes: molecular recognition of quinone and hydroquinone in solution.
2001-06-29
Role of aromatic stacking interactions in the modulation of the two-electron reduction potentials of flavin and substrate/product in Megasphaera elsdenii short-chain acyl-coenzyme A dehydrogenase.
2001-06-26
Electrogenic proton transfer in Rhodobacter sphaeroides reaction centers: effect of coenzyme Q(10) substitution by decylubiquinone in the Q(B) binding site.
2001-06-15
Surface control of oxidation by an adsorbed Ru(IV)-oxo complex.
2001-06-06
Isolation and study of some properties of laccase from the basidiomycetes Cerrena maxima.
2001-06
[Sensitization to resorcinol in a prescription verrucide preparation: unusual systemic clinical features and prevalence].
2001-05
Electron self-exchange in the solid-state: cocrystals of hydroquinone and bipyridyl triazole.
2001-03-28
Melasma treated with hydroquinone, tretinoin, and a fluorinated steroid.
2001-03
Exogenous ochronosis. An update on clinical features, causative agents and treatment options.
2001
Hypoxia and oxidative stress. Tumour hypoxia--therapeutic considerations.
2001
Two-photon ionization thresholds of matrix-assisted laser desorption/ionization matrix clusters.
2001
Use of in vitro assays to assess hematotoxic effects of environmental compounds.
2001
Patents

Sample Use Guides

TRI-LUMA Cream (fluocinolone acetonide 0.01%, hydroquinone 4%, tretinoin 0.05%) should be applied once daily at night. It should be applied at least 30 minutes before bedtime.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:40 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:40 GMT 2025
Record UNII
XV74C1N1AE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRI-LUMA COMPONENT HYDROQUINONE
Preferred Name English
Hydroquinone
HSDB   INCI   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
HYDROQUINONE [USP-RS]
Common Name English
BLACK AND WHITE BLEACHING CREAM
Brand Name English
NCI-C55834
Code English
NSC-9247
Code English
ELDOPAQUE FORTE
Brand Name English
HYDROQUINONE [USP MONOGRAPH]
Common Name English
CHEBI:17594
Code English
HYDROQUINONE [MI]
Common Name English
HYDROQUINONE [ORANGE BOOK]
Common Name English
HYDROQUINONE [HSDB]
Common Name English
ELDOQUIN FORTE
Brand Name English
SOLAQUIN FORTE
Brand Name English
1,4-BENZENEDIOL
Systematic Name English
HYDROQUINONE [MART.]
Common Name English
BUTYLHYDROXYANISOLE IMPURITY A [EP IMPURITY]
Common Name English
Hydroquinone [WHO-DD]
Common Name English
HYDROQUINONE [VANDF]
Common Name English
HYDROQUINONE [IARC]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45175
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
Food Contact Sustance Notif, (FCN No.) FCN NO. 1246
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
NDF-RT N0000175851
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
CFR 21 CFR 176.170
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
NDF-RT N0000175850
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
WHO-VATC QD11AX11
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
NDF-RT N0000175854
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
WHO-ATC D11AX11
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
Code System Code Type Description
MERCK INDEX
m6115
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL537
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
DRUG CENTRAL
3282
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
SMS_ID
100000077601
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
DAILYMED
XV74C1N1AE
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
CHEBI
17594
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
DRUG BANK
DB09526
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
RS_ITEM_NUM
1324002
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
PUBCHEM
785
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
RXCUI
5509
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID7020716
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
NCI_THESAURUS
C29823
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-617-8
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
NSC
9247
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
EVMPD
SUB14140MIG
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
FDA UNII
XV74C1N1AE
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
CAS
123-31-9
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
LACTMED
Hydroquinone
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
WIKIPEDIA
HYDROQUINONE
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
MESH
C031927
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
HSDB
577
Created by admin on Mon Mar 31 17:45:40 GMT 2025 , Edited by admin on Mon Mar 31 17:45:40 GMT 2025
PRIMARY
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