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Record Information
Version1.0
Created at2006-05-22 14:17:53 UTC
Updated at2021-10-07 20:40:50 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 forteHMDB
LustraHMDB
MelpaqueHMDB
Neostrata HQHMDB
Stratus brand 1 OF hydroquinoneHMDB
UltraquinHMDB
Hydroquinone, lead (2+) salt (2:1)HMDB
EsotericaHMDB
HidroquilaudeHMDB
ICN brand 1 OF hydroquinoneHMDB
MelquinHMDB
Plough brand 2 OF hydroquinoneHMDB
Hydroquinone, copper (1+) saltHMDB
ArtraHMDB
EldopaqueHMDB
Eldopaque forteHMDB
HidroquinHMDB
ICN brand 4 OF hydroquinoneHMDB
LicostrataHMDB
Hydroquinone, monocopper (2+) saltHMDB
Black and whiteHMDB
Hidroquinona isdinHMDB
ICN brand 2 OF hydroquinoneHMDB
ICN brand 3 OF hydroquinoneHMDB
MelanasaHMDB
Plough brand 1 OF hydroquinoneHMDB
SolaquinHMDB
Stratus brand 2 OF hydroquinoneHMDB
1,4-BenzoquinolHMDB
1,4-PhenylenediolHMDB
1,4-p-BenzenediolHMDB
p-DihydroquinoneHMDB
p-PhenylenediolHMDB
p-QuinolHMDB
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
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentus
Actinidia chinensis
Agaricus bisporus
Agave
Allium ampeloprasum
Allium ascalonicum
Allium cepa
Allium cepa L.
Allium fistulosum
Allium sativum
Allium schoenoprasum
Allium tuberosum
Aloysia triphylla
Amaranthus
Amelanchier alnifolia
Anacardium occidentale
Ananas comosus
Anethum graveolens
Angelica keiskei
Annona cherimola
Annona muricata
Annona reticulata
Annona squamosa
Anthriscus cerefolium
Apium graveolens
Apium graveolens var. dulce
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Arachis hypogaea
Arbutus unedoKNApSAcK Database
Arctium lappa
Armoracia rusticana
Artemisia dracunculus
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllus
Asparagus officinalis
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.
Averrhoa carambola
Basella alba
Benincasa hispida
Bertholletia excelsa
Beta vulgaris
Beta vulgaris ssp. cicla
Borago officinalis
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleracea
Brassica oleracea var. botrytis
Brassica oleracea var. capitata
Brassica oleracea var. gemmifera
Brassica oleracea var. gongylodes
Brassica oleracea var. italica
Brassica oleracea var. sabauda
Brassica oleracea var. viridis
Brassica rapa
Brassica rapa ssp. chinensis
Brassica rapa var. pekinensis
Brassica rapa var. rapa
Brassica ruvo
Brosimum alicastrum
Byrsonima crassifolia
Cajanus cajan
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Capparis spinosa
Capsicum annuum
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carvi
Carya
Carya illinoinensis
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Ceratonia siliqua
Chamaemelum nobile
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chrysanthemum coronarium
Cicer arietinum
Cichorium endivia
Cichorium intybus
Cinnamomum
Cinnamomum aromaticum
Cinnamomum verum
Cirsium
Citrullus lanatus
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifolia
Citrus latifolia
Citrus limon
Citrus maxima
Citrus paradisi
Citrus reticulata
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nucifera
Coffea arabica L.
Coffea canephora
Colocasia esculenta
Corchorus olitorius
Coriandrum sativum L.
Corylus
Corylus avellana
Crateva religiosa
Crocus sativus
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cuminum cyminum
Curcuma longa
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Daucus carota
Daucus carota ssp. sativus
Decussocarpus wallichianusKNApSAcK Database
Dimocarpus longan
Dioscorea
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Durio zibethinus
Dysidea cf.cristagalli-
Dysphania ambrosioides
Elaeis
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
Eragrostis tef
Eriobotrya japonica
Eruca vesicaria subsp. Sativa
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentum
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus carica
Flammulina velutipes
Foeniculum vulgare
Fragaria x ananassa
Garcinia mangostana
Gastrodia elataKNApSAcK Database
Gaylussacia baccata
Ginkgo biloba
Glycine max
Gossypium
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.
Helianthus tuberosus
Hibiscus sabbariffa
Hippophae rhamnoides
Hordeum vulgare
Hyssopus officinalis L.
Illicium verumFooDB
Ipomoea aquatica
Ipomoea batatas
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.
Juglans regia
Lablab purpureus
Lactuca sativa
Lagenaria siceraria
Lathyrus sativus
Laurus nobilis L.
Lens culinaris
Lentinus edodes
Lepidium sativum
Levisticum officinale
Linum usitatissimum
Litchi chinensis
Luffa aegyptiaca
Lupinus
Lupinus albus
Macadamia
Macadamia tetraphylla
Malpighia emarginata
Malus
Malus pumila
Mammea americana
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativa
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperita
Mespilus germanica
Metroxylon sagu
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Musa acuminata
Musa x paradisiaca
Myrica
Myristica fragrans
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
Nuphar lutea
Ocimum basilicum
Oenothera biennis
Olea europaea
Opuntia
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majoranaFooDB
Origanum onites
Origanum vulgare
Origanum X majoricum
Oryza rufipogon
Oryza sativa
Pachyrhizus erosus
Panax ginseng
Pangium edule
Panicum miliaceum
Passiflora edulis
Pastinaca sativa
Pediomelum esculentum
Perideridia oregana
Persea americana
Petasites japonicus
Petroselinum crispum
Petroselinum spp.KNApSAcK Database
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgaris
Phoenix dactylifera
Photinia melanocarpa
Phyllostachys edulis
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioica
Pimpinella anisumKNApSAcK Database
Pinus
Pinus edulis
Pinus resinosaKNApSAcK Database
Pinus sibiricaKNApSAcK Database
Piper nigrum L.
Pistacia vera
Pisum sativum
Pleurotus ostreatus
Polygonum alpinum
Portulaca oleracea
Pouteria sapota
Primula ovalifoliaPlant
Protea melliferaKNApSAcK Database
Prunus armeniaca
Prunus avium
Prunus avium L.
Prunus cerasus
Prunus domestica
Prunus dulcis
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Punica granatum
Pyrus communisKNApSAcK Database
Pyrus pyrifolia
Quercus
Raphanus sativus
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Rheum rhabarbarum
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrum
Ribes uva-crispa
Rosa
Rubus arcticus
Rubus chamaemorus
Rubus idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Salix pulchra
Salvia elegans
Salvia hispanica
Salvia officinalis
Salvia rosmarinus
Sambucus nigra
Sambucus nigra L.
Satureja hortensis L.
Satureja montana
Scorzonera hispanica
Secale cereale
Sechium edule
Sesamum indicum
Sesbania bispinosa
Sinapis alba
Sisymbrium
Solanum lycopersicum
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongena
Solanum quitoense
Solanum tuberosum
Sorbus aucuparia
Sorghum bicolor
Spinacia oleracea
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Taraxacum officinale
Tetragonia tetragonioides
Thelesperma
Thymus pulegioides
Thymus vulgaris
Tilia cordata
Tilia L.
Tragopogon porrifolius
Trigonella foenum-graecum
Triticum
Triticum aestivum
Triticum durum
Triticum spelta
Triticum turanicum
Typha angustifolia
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillusFooDB
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaeaKNApSAcK Database
Valerianella locusta
Vanilla
Verbena officinalis
Viburnum edule
Vicia faba
Vigna aconitifolia
Vigna angularis
Vigna mungo
Vigna radiata
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
Vitis
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.
Xanthium canadenseKNApSAcK Database
Xanthosoma sagittifolium
Zea mays L.
Zingiber officinale
Zizania
Zizania aquatica
Ziziphus zizyphus
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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (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
HMDB IDHMDB0002434
DrugBank IDDB09526
Phenol Explorer Compound ID660
FoodDB IDFDB030688
KNApSAcK IDC00002656
Chemspider ID764
KEGG Compound IDC00530
BioCyc IDHYDROQUINONE
BiGG IDNot Available
Wikipedia LinkHydroquinone
METLIN ID6681
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 ]