Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:29 UTC
HMDB IDHMDB0001164
Secondary Accession Numbers
  • HMDB01164
Metabolite Identification
Common Nametrans-1,2-Dihydrobenzene-1,2-diol
Descriptiontrans-1,2-Dihydrobenzene-1,2-diol belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. trans-1,2-Dihydrobenzene-1,2-diol has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make trans-1,2-dihydrobenzene-1,2-diol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on trans-1,2-Dihydrobenzene-1,2-diol.
Structure
Data?1676999729
Synonyms
ValueSource
(1R,2R)-1,2-Dihydrobenzene-1,2-diolChEBI
Arene diolHMDB
cis-3,5-Cyclohexadiene-1,2-diol solutionHMDB
Racemic mixture OF (+)- and (-)-1,2-dihydroxy-1,2-dihydrobenzeneHMDB
Rel-(1R,2R)-cyclohexa-3,5-diene-1,2-diolHMDB
trans-(+-)-3,5-Cyclohexadiene-1,2-diolHMDB
trans-3,5-Cyclohexadiene-1,2-diolHMDB
trans-1,2-Dihydrobenzene-1,2-diolChEBI
Chemical FormulaC6H8O2
Average Molecular Weight112.1265
Monoisotopic Molecular Weight112.0524295
IUPAC Name(1R,2R)-cyclohexa-3,5-diene-1,2-diol
Traditional Namearene diol
CAS Registry Number103302-38-1
SMILES
O[C@@H]1C=CC=C[C@H]1O
InChI Identifier
InChI=1S/C6H8O2/c7-5-3-1-2-4-6(5)8/h1-8H/t5-,6-/m1/s1
InChI KeyYDRSQRPHLBEPTP-PHDIDXHHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility178 g/LALOGPS
logP-0.18ALOGPS
logP-0.21ChemAxon
logS0.2ALOGPS
pKa (Strongest Acidic)13.47ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.56 m³·mol⁻¹ChemAxon
Polarizability11.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+122.36631661259
DarkChem[M-H]-117.04431661259
AllCCS[M+H]+126.59232859911
AllCCS[M-H]-120.73632859911
DeepCCS[M+H]+128.41230932474
DeepCCS[M-H]-126.31230932474
DeepCCS[M-2H]-161.83130932474
DeepCCS[M+Na]+136.14730932474
AllCCS[M+H]+126.632859911
AllCCS[M+H-H2O]+121.732859911
AllCCS[M+NH4]+131.232859911
AllCCS[M+Na]+132.532859911
AllCCS[M-H]-120.732859911
AllCCS[M+Na-2H]-123.332859911
AllCCS[M+HCOO]-126.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-1,2-Dihydrobenzene-1,2-diolO[C@@H]1C=CC=C[C@H]1O1775.8Standard polar33892256
trans-1,2-Dihydrobenzene-1,2-diolO[C@@H]1C=CC=C[C@H]1O1092.5Standard non polar33892256
trans-1,2-Dihydrobenzene-1,2-diolO[C@@H]1C=CC=C[C@H]1O1059.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-1,2-Dihydrobenzene-1,2-diol,1TMS,isomer #1C[Si](C)(C)O[C@@H]1C=CC=C[C@H]1O1248.3Semi standard non polar33892256
trans-1,2-Dihydrobenzene-1,2-diol,2TMS,isomer #1C[Si](C)(C)O[C@@H]1C=CC=C[C@H]1O[Si](C)(C)C1301.2Semi standard non polar33892256
trans-1,2-Dihydrobenzene-1,2-diol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C=CC=C[C@H]1O1467.2Semi standard non polar33892256
trans-1,2-Dihydrobenzene-1,2-diol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C=CC=C[C@H]1O[Si](C)(C)C(C)(C)C1722.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfu-9000000000-36be6170d6aeb143432b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-9710000000-3400c66fcd577a2df0222017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 10V, Positive-QTOFsplash10-03di-1900000000-d7121c202776bf3f1ff82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 20V, Positive-QTOFsplash10-03di-5900000000-51396982b568c547b4fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 40V, Positive-QTOFsplash10-0udl-9000000000-db963106694d68d1163c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 10V, Negative-QTOFsplash10-03di-0900000000-983307a7cfa91742b0da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 20V, Negative-QTOFsplash10-03di-1900000000-185fc58f8f3b52505cdd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 40V, Negative-QTOFsplash10-0ik9-9300000000-9f1f8262efe5adb2f0c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 10V, Positive-QTOFsplash10-0002-9000000000-e3d808ea4d2d2f328d1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 20V, Positive-QTOFsplash10-0uxs-9000000000-b7cca48fb6c1e036eb1b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 40V, Positive-QTOFsplash10-0gbi-9000000000-569b7f3fc872051f9af92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 10V, Negative-QTOFsplash10-03di-3900000000-e87e4c500aa5823cd2592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 20V, Negative-QTOFsplash10-0006-9100000000-6db11e4f5f30c8c63a0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 40V, Negative-QTOFsplash10-0006-9000000000-b39a7571486a5e8d439c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022458
KNApSAcK IDNot Available
Chemspider ID131491
KEGG Compound IDC04221
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound149186
PDB IDNot Available
ChEBI ID10702
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSato, Tokuro; Fukuyama, Tomitaro; Suzuki, Taeko; Yoshikawa, Haruhisa. 1,2-Dihydro-1,2-dihydroxybenzene and several other substances in the metabolism of benzene. Journal of Biochemistry (Tokyo, Japan) (1963), 53 23-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DHDH
Uniprot ID:
Q9UQ10
Molecular weight:
36381.705
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails