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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:29 UTC

HMDB ID

HMDB0001164

Secondary Accession Numbers

HMDB01164

Metabolite Identification

Common Name

trans-1,2-Dihydrobenzene-1,2-diol

Description

trans-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1R,2R)-1,2-Dihydrobenzene-1,2-diol	ChEBI
Arene diol	HMDB
cis-3,5-Cyclohexadiene-1,2-diol solution	HMDB
Racemic mixture OF (+)- and (-)-1,2-dihydroxy-1,2-dihydrobenzene	HMDB
Rel-(1R,2R)-cyclohexa-3,5-diene-1,2-diol	HMDB
trans-(+-)-3,5-Cyclohexadiene-1,2-diol	HMDB
trans-3,5-Cyclohexadiene-1,2-diol	HMDB
trans-1,2-Dihydrobenzene-1,2-diol	ChEBI

Chemical Formula

C₆H₈O₂

Average Molecular Weight

112.1265

Monoisotopic Molecular Weight

112.0524295

IUPAC Name

(1R,2R)-cyclohexa-3,5-diene-1,2-diol

Traditional Name

arene diol

CAS Registry Number

103302-38-1

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 Key

YDRSQRPHLBEPTP-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-diols

Alternative Parents

Substituents

Secondary alcohol
1,2-diol
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

trans-cyclohexa-3,5-diene-1,2-diol (CHEBI:10702 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001164)

Source

Endogenous

Endogenous (HMDB: HMDB0001164)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	178 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	-0.21	ChemAxon
logS	0.2	ALOGPS
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	32.56 m³·mol⁻¹	ChemAxon
Polarizability	11.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	122.366	31661259
DarkChem	[M-H]-	117.044	31661259
AllCCS	[M+H]+	126.592	32859911
AllCCS	[M-H]-	120.736	32859911
DeepCCS	[M+H]+	128.412	30932474
DeepCCS	[M-H]-	126.312	30932474
DeepCCS	[M-2H]-	161.831	30932474
DeepCCS	[M+Na]+	136.147	30932474
AllCCS	[M+H]+	126.6	32859911
AllCCS	[M+H-H2O]+	121.7	32859911
AllCCS	[M+NH4]+	131.2	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	120.7	32859911
AllCCS	[M+Na-2H]-	123.3	32859911
AllCCS	[M+HCOO]-	126.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-1,2-Dihydrobenzene-1,2-diol	O[C@@H]1C=CC=C[C@H]1O	1775.8	Standard polar	33892256
trans-1,2-Dihydrobenzene-1,2-diol	O[C@@H]1C=CC=C[C@H]1O	1092.5	Standard non polar	33892256
trans-1,2-Dihydrobenzene-1,2-diol	O[C@@H]1C=CC=C[C@H]1O	1059.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-1,2-Dihydrobenzene-1,2-diol,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C=CC=C[C@H]1O	1248.3	Semi standard non polar	33892256
trans-1,2-Dihydrobenzene-1,2-diol,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1C=CC=C[C@H]1O[Si](C)(C)C	1301.2	Semi standard non polar	33892256
trans-1,2-Dihydrobenzene-1,2-diol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C=CC=C[C@H]1O	1467.2	Semi standard non polar	33892256
trans-1,2-Dihydrobenzene-1,2-diol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C=CC=C[C@H]1O[Si](C)(C)C(C)(C)C	1722.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfu-9000000000-36be6170d6aeb143432b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol GC-MS (2 TMS) - 70eV, Positive	splash10-00xu-9710000000-3400c66fcd577a2df022	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 10V, Positive-QTOF	splash10-03di-1900000000-d7121c202776bf3f1ff8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 20V, Positive-QTOF	splash10-03di-5900000000-51396982b568c547b4fb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 40V, Positive-QTOF	splash10-0udl-9000000000-db963106694d68d1163c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 10V, Negative-QTOF	splash10-03di-0900000000-983307a7cfa91742b0da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 20V, Negative-QTOF	splash10-03di-1900000000-185fc58f8f3b52505cdd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 40V, Negative-QTOF	splash10-0ik9-9300000000-9f1f8262efe5adb2f0c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 10V, Positive-QTOF	splash10-0002-9000000000-e3d808ea4d2d2f328d1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 20V, Positive-QTOF	splash10-0uxs-9000000000-b7cca48fb6c1e036eb1b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 40V, Positive-QTOF	splash10-0gbi-9000000000-569b7f3fc872051f9af9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 10V, Negative-QTOF	splash10-03di-3900000000-e87e4c500aa5823cd259	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 20V, Negative-QTOF	splash10-0006-9100000000-6db11e4f5f30c8c63a0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-1,2-Dihydrobenzene-1,2-diol 40V, Negative-QTOF	splash10-0006-9000000000-b39a7571486a5e8d439c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022458

KNApSAcK ID

Not Available

Chemspider ID

131491

KEGG Compound ID

C04221

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

149186

PDB ID

Not Available

ChEBI ID

10702

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Sato, 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 References

Not Available

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

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

Enzyme Details

2. Aldo-keto reductase family 1 member C3

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 + NADPH	details

Enzyme Details

3. Aldo-keto reductase family 1 member C1

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 + NADPH	details

Enzyme Details

4. Aldo-keto reductase family 1 member C2

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 + NADPH	details

Enzyme Details

5. Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase

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 + NADPH	details

Showing metabocard for trans-1,2-Dihydrobenzene-1,2-diol (HMDB0001164)

MOL for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

3D MOL for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

3D SDF for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

3D-SDF for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

PDB for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

3D PDB for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

SMILES for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

INCHI for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

Structure for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

3D Structure for HMDB0001164 (trans-1,2-Dihydrobenzene-1,2-diol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions