1,3-Benzenediol (T3D4580)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (12)XML
Targets (12)
Record Information
Version2.0
Creation Date2014-09-05 17:10:29 UTC
Update Date2014-12-24 20:26:52 UTC
Accession NumberT3D4580
Identification
Common Name1,3-Benzenediol
ClassSmall Molecule
Description1,3-Benzenediol is found in alcoholic beverages. 1,3-Benzenediol is present in roasted barley, cane molasses, coffee, beer and wine. 1,3-Benzenediol is a flavouring ingredient1,3-Benzenediol belongs to the family of Resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydrocyl groups at positions 1 and 3.
Compound Type
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1,3-Dihydroxy-Benzene
1,3-Dihydroxybenzene
3-Hydroxyphenol
FEMA 3589
m-Benzenediol
m-Dihydroxybenzene
m-Dioxybenzene
m-Hydroquinone
m-Hydroxy-Phenol
m-Hydroxyphenol
Resorcin
Resorcinol, 8CI
Resorzin
Rezorsine
Chemical FormulaC6H6O2
Average Molecular Mass110.111 g/mol
Monoisotopic Mass110.037 g/mol
CAS Registry Number108-46-3
IUPAC Namebenzene-1,3-diol
Traditional Nameresorcinol
SMILESOC1=CC(O)=CC=C1
InChI IdentifierInChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
InChI KeyInChIKey=GHMLBKRAJCXXBS-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point111 °C
Boiling PointNot Available
Solubility717 mg/mL at 25 °C
LogP0.8
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-08gi-9600000000-0e7d24e90c380c2fbaf52017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9500000000-02f0a9b7ce8b4af474732017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03e9-9300000000-fcd22d3e2208eda085dd2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f83-3960000000-6169d32b43f71f4abe1a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-08gi-9600000000-0e7d24e90c380c2fbaf52018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9500000000-02f0a9b7ce8b4af474732018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03e9-9300000000-fcd22d3e2208eda085dd2018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f83-3960000000-6169d32b43f71f4abe1a2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3900000000-523ce2d2022aff1e83072017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ei-7940000000-20d1bf1b6588a896d3812017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-64036e30d95c257972de2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-e75dbf262b9b2cf88b202016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9300000000-6fec697f0a62d05e07402016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-390a7eb266152d83c9252021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6900000000-ad5c8e451745f725a8982021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8b485ce5f0cbe4811afb2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-920e234b400dba4e5f872016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-b7e895b1f7ab851eecff2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-9300000000-91340faf902dd2ba7d1f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-fd10fd64675560620b8d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-9600000000-b1d387d2d4ab01180df92021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-596a7612f830d3e5368f2021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-8900000000-3771649f063971fd96f32014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (3)
Uses/Sources1,3-Benzenediol is found in alcoholic beverages.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB32037
PubChem Compound ID5054
ChEMBL IDCHEMBL24147
ChemSpider ID4878
KEGG IDC01751
UniProt IDNot Available
OMIM ID
ChEBI ID27810
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDRCO
ACToR IDNot Available
Wikipedia Link1,3-Benzenediol
References
Synthesis ReferenceNot Available
MSDST3D4580.pdf
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  2. Halliwell, Barry B., and Henrik E. Poulsen (2006). Cigarette Smoke and Oxidative Stress. Berlin: Springer. [ISBN: 978-3-540-31410-3 (Print) 978-3-540-32232-0 (Online)]
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Carbonic anhydrase 1
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular Weight:
28870.0 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory795 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Hilvo M, Scozzafava A, Parkkila S, Supuran CT: Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3593-6. doi: 10.1016/j.bmcl.2008.04.077. Epub 2008 May 4. [18501600 ]
  2. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
2. Carbonic anhydrase 2
General Function:
Zinc ion binding
Specific Function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular Weight:
29245.895 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory7.7 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Hilvo M, Scozzafava A, Parkkila S, Supuran CT: Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3593-6. doi: 10.1016/j.bmcl.2008.04.077. Epub 2008 May 4. [18501600 ]
  2. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
3. Carbonic anhydrase 12
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA12
Uniprot ID:
O43570
Molecular Weight:
39450.615 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory7.5 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
4. Carbonic anhydrase 14
General Function:
Metal ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA14
Uniprot ID:
Q9ULX7
Molecular Weight:
37667.37 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory10.7 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
5. Carbonic anhydrase 3
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA3
Uniprot ID:
P07451
Molecular Weight:
29557.215 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory605 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
6. Carbonic anhydrase 4
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular Weight:
35032.075 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory570 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
7. Carbonic anhydrase 5A, mitochondrial
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Low activity.
Gene Name:
CA5A
Uniprot ID:
P35218
Molecular Weight:
34750.21 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory8.7 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
8. Carbonic anhydrase 5B, mitochondrial
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA5B
Uniprot ID:
Q9Y2D0
Molecular Weight:
36433.43 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory7.1 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
9. Carbonic anhydrase 6
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Its role in saliva is unknown.
Gene Name:
CA6
Uniprot ID:
P23280
Molecular Weight:
35366.615 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory550 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
10. Carbonic anhydrase 7
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA7
Uniprot ID:
P43166
Molecular Weight:
29658.235 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory644 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
11. Carbonic anhydrase 9
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
Gene Name:
CA9
Uniprot ID:
Q16790
Molecular Weight:
49697.36 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory69.7 uMNot AvailableBindingDB 26189
References
  1. Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
Target Details
12. Cytochrome P450 3A4
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.80 uMNVS_ADME_hCYP3A4Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]