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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:23 UTC
Update Date2019-07-23 06:10:10 UTC
HMDB IDHMDB0032037
Secondary Accession Numbers
  • HMDB32037
Metabolite Identification
Common Name1,3-Benzenediol
Description1,3-Benzenediol, also known as resorcin or m-hydroquinone, belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 1,3-Benzenediol is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,3-Benzenediol exists in all living organisms, ranging from bacteria to humans. 1,3-Benzenediol is a creamy, hawthorn, and musty tasting compound. Outside of the human body, 1,3-Benzenediol has been detected, but not quantified in, several different foods, such as alcoholic beverages, cereals and cereal products, coffee and coffee products, eggplants, and java plums. This could make 1,3-benzenediol a potential biomarker for the consumption of these foods. 1,3-Benzenediol is a potentially toxic compound. In addition, exogenous ochronosis is associated with prolonged exposure to resorcinol . Data regarding the specific mechanisms of action of resorcinol does not appear to be readily accessible in the literature. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated . Resorcinol works by helping to remove hard, scaly, or roughened skin. In particular, it appears that resorcinol indicated for treating acne, dermatitis, or eczema in various skin care topical applications and peels revolves around the compound's ability to precipitate cutaneous proteins from the treated skin . In LPO and TPO, the resulting π-cation radical of the porphyrin can isomerize to a radical cation with the radical in an aromatic side chain of the enzyme . In vitro and in vivo studies have demonstrated that resorcinol can inhibit peroxidases in the thyroid and subsequently block the synthesis of thyroid hormones and cause goiter .
Structure
Data?1563862210
Synonyms
ValueSource
1,3-DihydroxybenzeneChEBI
1,3-DihydroxybenzolChEBI
m-HydroquinoneChEBI
m-HydroxyphenolChEBI
ResorcinChEBI
ResorzinChEBI
1,3-Dihydroxy-benzeneHMDB
3-HydroxyphenolHMDB
FEMA 3589HMDB
m-BenzenediolHMDB
m-DihydroxybenzeneHMDB
m-DioxybenzeneHMDB
m-Hydroxy-phenolHMDB
Resorcinol, 8ciHMDB
RezorsineHMDB
Resorcinol, monocopper (2+) saltMeSH
Resorcinol disodium saltMeSH
1,3-BenzenediolChEBI
Chemical FormulaC6H6O2
Average Molecular Weight110.1106
Monoisotopic Molecular Weight110.036779436
IUPAC Namebenzene-1,3-diol
Traditional Nameresorcinol
CAS Registry Number108-46-3
SMILES
OC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
InChI KeyGHMLBKRAJCXXBS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentResorcinols
Alternative Parents
Substituents
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point111 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility717 mg/mL at 25 °CNot Available
LogP0.80Not Available
Predicted Properties
PropertyValueSource
Water Solubility82.3 g/LALOGPS
logP0.7ALOGPS
logP1.37ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)9.26ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-08gi-9600000000-0e7d24e90c380c2fbaf5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9500000000-02f0a9b7ce8b4af47473Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03e9-9300000000-fcd22d3e2208eda085ddSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f83-3960000000-6169d32b43f71f4abe1aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-08gi-9600000000-0e7d24e90c380c2fbaf5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9500000000-02f0a9b7ce8b4af47473Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03e9-9300000000-fcd22d3e2208eda085ddSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f83-3960000000-6169d32b43f71f4abe1aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3900000000-523ce2d2022aff1e8307Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ei-7940000000-20d1bf1b6588a896d381Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-920e234b400dba4e5f87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-b7e895b1f7ab851eecffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-9300000000-91340faf902dd2ba7d1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-64036e30d95c257972deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-e75dbf262b9b2cf88b20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9300000000-6fec697f0a62d05e0740Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-8900000000-3771649f063971fd96f3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11085
Phenol Explorer Compound ID663
FooDB IDFDB008738
KNApSAcK IDC00002671
Chemspider ID4878
KEGG Compound IDC01751
BioCyc IDCPD-623
BiGG IDNot Available
Wikipedia LinkResorcinol
METLIN IDNot Available
PubChem Compound5054
PDB IDRCO
ChEBI ID27810
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
1,3-Benzenediol → 3,4,5-trihydroxy-6-(3-hydroxyphenoxy)oxane-2-carboxylic aciddetails