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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRI-LUMA

Cmax

ValueDoseCo-administeredAnalytePopulation
56.035 ng/mL
1 g single, topical
HYDROQUINONE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
XV74C1N1AE
Record Status Validated (UNII)
Record Version