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Hydroquinone (FDB000885)

Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2019-11-26 02:55:34 UTC
Primary IDFDB000885
Secondary Accession Numbers
  • FDB030688
Chemical Information
FooDB NameHydroquinone
DescriptionHydroquinone, also 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 in most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver. [HMDB]. Hydroquinone is found in many foods, some of which are kai-lan, agar, red bell pepper, and jostaberry.
CAS Number123-31-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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
Chemical FormulaC6H6O2
IUPAC namebenzene-1,4-diol
InChI IdentifierInChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
InChI KeyQIGBRXMKCJKVMJ-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(O)C=C1
Average Molecular Weight110.1106
Monoisotopic Molecular Weight110.036779436
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 65.45%; H 5.49%; O 29.06%DFC
Melting PointNot Available
Boiling PointBp730 285°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 250 (e 204) (CHCl3) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03di-9500000000-1fa8477944a662535e762014-09-20View Spectrum
GC-MSHydroquinone, 2 TMS, GC-MS Spectrumsplash10-0f79-2490000000-6b4fec222a3499d93790Spectrum
GC-MSHydroquinone, non-derivatized, GC-MS Spectrumsplash10-03di-9800000000-c90fd4986fea9691ecbfSpectrum
GC-MSHydroquinone, non-derivatized, GC-MS Spectrumsplash10-03e9-9300000000-f8b11742557329691e8aSpectrum
GC-MSHydroquinone, non-derivatized, GC-MS Spectrumsplash10-0f79-2490000000-6b4fec222a3499d93790Spectrum
GC-MSHydroquinone, non-derivatized, GC-MS Spectrumsplash10-0f79-2690000000-7306adcc7121a11d67ccSpectrum
Predicted GC-MSHydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-5900000000-954dc96d8e3eb85b8324Spectrum
Predicted GC-MSHydroquinone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-8950000000-512c0cf5ddc0b120ec8eSpectrum
Predicted GC-MSHydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9600000000-e670ba090cb27367db122012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01p6-9000000000-5fc32c7688c1612df1e72012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-c5853ce8ef225ea5c3532012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-03di-9800000000-c90fd4986fea9691ecbf2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-5635f0157cd37deb11212017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-2900000000-05be113033a709130eed2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9600000000-e0d15b2e4ea35a7a76be2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01r6-9000000000-946504408977df40269a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-c16180dd26c1275631552021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-cea1cb486f12ea31e3a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01ox-9000000000-3a9d5710c88793e698f12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-60eeaa79bff371773b2e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3a9e293da186985db7fa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-84bb0a9b4c3cd16da2a72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-7900000000-2256214c81a3e04e01b72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-8d8328e4f7cd2ebaa27d2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-9290fcb93f170fc3143f2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01si-9200000000-9f707b9d0c4ad0b73b302015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-d3aae38632ac4c40fd4f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-74f15490ba4f49cf8c182015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-1cb01248e88fce3875782015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9f2c82efe2cba7470e172021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-9f2c82efe2cba7470e172021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9000000000-8213c13cc381b346f9762021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-fd10fd64675560620b8d2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID764
ChEMBL IDCHEMBL537
KEGG Compound IDC00530
Pubchem Compound ID785
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID660
DrugBank IDNot Available
HMDB IDHMDB02434
CRC / DFC (Dictionary of Food Compounds) IDBLQ78-M:BLQ78-M
EAFUS IDNot Available
Dr. Duke IDHYDROQUINONE|P-HYDROQUINONE
BIGG IDNot Available
KNApSAcK IDC00002656
HET IDHQE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelochemicDUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti hepatomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti lithicDUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti melasmicDUKE
anti menorrhagic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti mitoticDUKE
anti nephritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti pertussive33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti thyreotropicDUKE
anti trypanosomic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
astringent74783 A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
convulsantDUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
deliriantDUKE
depigmentorDUKE
emeticDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
hypertensiveDUKE
irritantDUKE
mycoplasmistatDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
tinnitigenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
Enzymes
NameGene NameUniProt ID
Serum paraoxonase/lactonase 3PON3Q15166
Serum paraoxonase/arylesterase 1PON1P27169
Serum paraoxonase/arylesterase 2PON2Q15165
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.