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Record Information
Version1.0
Created at2006-05-22 14:17:53 UTC
Updated at2021-08-19 23:58:07 UTC
NP-MRD IDNP0000447
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroquinone
DescriptionHydroquinone, also known as benzene-1,4-diol, is an aromatic organic compound which is a type of phenol, having the chemical formula C6H4(OH)2. Its chemical structure has two hydroxyl groups bonded to a benzene ring in a para position. Hydroquinone is commonly used as a biomarker for benzene exposure. The presence of hydroquinone in normal individuals stems mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin-containing foods, cigarette smoking, and the use of some over-the-counter medicines. Hydroquinone is a white granular solid at room temperature and pressure. The hydroxyl groups of hydroquinone are quite weakly acidic. Hydroquinone can lose an H+ from one of the hydroxyls to form a monophenolate ion or lose an H+ from both to form a diphenolate ion. Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. It is a major component of most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver.
Structure
Thumb
Synonyms
ValueSource
1,4-BenzenediolChEBI
1,4-DihydroxybenzeneChEBI
4-HydroxyphenolChEBI
Benzene-1,4-diolChEBI
EldoquinChEBI
p-BenzenediolChEBI
p-HydroquinoneChEBI
p-HydroxyphenolChEBI
QuinolChEBI
1,4-Dihydroxy-benzeenHMDB
1,4-Dihydroxy-benzolHMDB
1,4-DihydroxybenzenHMDB
1,4-DiidrobenzeneHMDB
a-HydroquinoneHMDB
alpha-HydroquinoneHMDB
b-QuinolHMDB
BenzohydroquinoneHMDB
BenzoquinolHMDB
beta-QuinolHMDB
DihydroquinoneHMDB
DihydroxybenzeneHMDB
HydrochinonHMDB
HydrochinoneHMDB
HydroquinolHMDB
HydroquinoleHMDB
Hydroquinone for synthesisHMDB
Hydroquinone GRHMDB
HydroquinoueHMDB
IdrochinoneHMDB
MelanexHMDB
p-DihydroxybenzeneHMDB
P-DioxobenzeneHMDB
p-DioxybenzeneHMDB
P-HydroxybenzeneHMDB
PhiaquinHMDB
Solaquin forteHMDB
Eldoquin forteMeSH, HMDB
LustraMeSH, HMDB
MelpaqueMeSH, HMDB
Neostrata HQMeSH, HMDB
Stratus brand 1 OF hydroquinoneMeSH, HMDB
UltraquinMeSH, HMDB
Hydroquinone, lead (2+) salt (2:1)MeSH, HMDB
EsotericaMeSH, HMDB
HidroquilaudeMeSH, HMDB
ICN brand 1 OF hydroquinoneMeSH, HMDB
MelquinMeSH, HMDB
Plough brand 2 OF hydroquinoneMeSH, HMDB
Hydroquinone, copper (1+) saltMeSH, HMDB
ArtraMeSH, HMDB
EldopaqueMeSH, HMDB
Eldopaque forteMeSH, HMDB
HidroquinMeSH, HMDB
ICN brand 4 OF hydroquinoneMeSH, HMDB
LicostrataMeSH, HMDB
Hydroquinone, monocopper (2+) saltMeSH, HMDB
Black and whiteMeSH, HMDB
Hidroquinona isdinMeSH, HMDB
ICN brand 2 OF hydroquinoneMeSH, HMDB
ICN brand 3 OF hydroquinoneMeSH, HMDB
MelanasaMeSH, HMDB
Plough brand 1 OF hydroquinoneMeSH, HMDB
SolaquinMeSH, HMDB
Stratus brand 2 OF hydroquinoneMeSH, HMDB
1,4-BenzoquinolPhytoBank
1,4-PhenylenediolPhytoBank
1,4-p-BenzenediolPhytoBank
p-DihydroquinonePhytoBank
p-PhenylenediolPhytoBank
p-QuinolPhytoBank
Chemical FormulaC6H6O2
Average Mass110.1106 Da
Monoisotopic Mass110.03678 Da
IUPAC Namebenzene-1,4-diol
Traditional Nameα-hydroquinone
CAS Registry Number123-31-9
SMILES
OC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
InChI KeyQIGBRXMKCJKVMJ-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Arbutus unedoKNApSAcK Database
Decussocarpus wallichianusKNApSAcK Database
Gastrodia elataKNApSAcK Database
Petroselinum spp.KNApSAcK Database
Pimpinella anisumKNApSAcK Database
Pinus resinosaKNApSAcK Database
Pinus sibiricaKNApSAcK Database
Protea melliferaKNApSAcK Database
Pyrus communisKNApSAcK Database
Vaccinium vitis-idaeaKNApSAcK Database
Xanthium canadenseKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentHydroquinones
Alternative Parents
Substituents
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point172.3 °CNot Available
Boiling Point286.00 to 288.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility72 mg/mL at 25 °CNot Available
LogP0.59HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility95.5 g/LALOGPS
logP0.71ALOGPS
logP1.37ChemAxon
logS-0.06ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.02 m³·mol⁻¹ChemAxon
Polarizability10.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0002434
DrugBank IDDB09526
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000885
KNApSAcK IDC00002656
Chemspider ID764
KEGG Compound IDC00530
BioCyc IDHYDROQUINONE
BiGG IDNot Available
Wikipedia LinkHydroquinone
METLIN IDNot Available
PubChem Compound785
PDB IDNot Available
ChEBI ID17594
Good Scents IDrw1250911
References
General References
  1. McDonald TA, Holland NT, Skibola C, Duramad P, Smith MT: Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia. Leukemia. 2001 Jan;15(1):10-20. [PubMed:11243376 ]
  2. Gaskell M, McLuckie KI, Farmer PB: Comparison of the repair of DNA damage induced by the benzene metabolites hydroquinone and p-benzoquinone: a role for hydroquinone in benzene genotoxicity. Carcinogenesis. 2005 Mar;26(3):673-80. Epub 2004 Dec 23. [PubMed:15618234 ]
  3. Inayat-Hussain SH, McGuinness SM, Johansson R, Lundstrom J, Ross D: Caspase-dependent and -independent mechanisms in apoptosis induced by hydroquinone and catechol metabolites of remoxipride in HL-60 cells. Chem Biol Interact. 2000 Aug 15;128(1):51-63. [PubMed:10996300 ]
  4. Carbonnelle P, Lison D, Leroy JY, Lauwerys R: Effect of the benzene metabolite, hydroquinone, on interleukin-1 secretion by human monocytes in vitro. Toxicol Appl Pharmacol. 1995 Jun;132(2):220-6. [PubMed:7540334 ]
  5. Keh ES, Hayakawa I, Takahashi H, Watanabe A, Iwasaki Y, Akiyoshi K, Nakabayashi N: Improving a self-curing dental resin by eliminating oxygen, hydroquinone and water from its curing process. Dent Mater J. 2002 Dec;21(4):373-82. [PubMed:12608426 ]
  6. Subrahmanyam VV, Kolachana P, Smith MT: Hydroxylation of phenol to hydroquinone catalyzed by a human myeloperoxidase-superoxide complex: possible implications in benzene-induced myelotoxicity. Free Radic Res Commun. 1991;15(5):285-96. [PubMed:1666626 ]
  7. Li X, Zhuang Z, Liu J, Huang H, Wei Q, Yang X: [Protein changes in human embryonic lung fibroblasts after hydroquinone stimulation using proteomic technique]. Wei Sheng Yan Jiu. 2004 Nov;33(6):654-7. [PubMed:15727168 ]
  8. Bucks DA, McMaster JR, Guy RH, Maibach HI: Percutaneous absorption of hydroquinone in humans: effect of 1-dodecylazacycloheptan-2-one (azone) and the 2-ethylhexyl ester of 4-(dimethylamino)benzoic acid (Escalol 507). J Toxicol Environ Health. 1988;24(3):279-89. [PubMed:3260963 ]
  9. Barber ED, Hill T, Schum DB: The percutaneous absorption of hydroquinone (HQ) through rat and human skin in vitro. Toxicol Lett. 1995 Oct;80(1-3):167-72. [PubMed:7482585 ]
  10. Boyle J, Kennedy CT: Hydroquinone concentrations in skin lightening creams. Br J Dermatol. 1986 Apr;114(4):501-4. [PubMed:3964548 ]
  11. Nilsson LB: High sensitivity determination of the remoxipride hydroquinone metabolite NCQ-344 in plasma by coupled column reversed-phase liquid chromatography and electrochemical detection. Biomed Chromatogr. 1998 Mar-Apr;12(2):65-8. [PubMed:9568272 ]
  12. Oliveira NL, Kalf GF: Induced differentiation of HL-60 promyelocytic leukemia cells to monocyte/macrophages is inhibited by hydroquinone, a hematotoxic metabolite of benzene. Blood. 1992 Feb 1;79(3):627-33. [PubMed:1732008 ]
  13. Wester RC, Melendres J, Hui X, Cox R, Serranzana S, Zhai H, Quan D, Maibach HI: Human in vivo and in vitro hydroquinone topical bioavailability, metabolism, and disposition. J Toxicol Environ Health A. 1998 Jun 26;54(4):301-17. [PubMed:9638901 ]
  14. Kooyers TJ, Westerhof W: [Toxicological aspects and health risks associated with hydroquinone in skin bleaching formula]. Ned Tijdschr Geneeskd. 2004 Apr 17;148(16):768-71. [PubMed:15129564 ]