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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:15 UTC

Update Date

2023-02-21 17:21:28 UTC

HMDB ID

HMDB0032019

Secondary Accession Numbers

HMDB32019

Metabolite Identification

Common Name

2,6-Dimethylbenzenethiol

Description

2,6-Dimethylbenzenethiol belongs to the class of organic compounds known as thiophenols. Thiophenols are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom. 2,6-Dimethylbenzenethiol is a meaty, metallic, and phenolic tasting compound. Based on a literature review very few articles have been published on 2,6-Dimethylbenzenethiol.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
26-Dimethyl-benzenethiol	ChEMBL, HMDB
2,6-Dimethyl thiophenol	HMDB
2,6-Dimethyl-benzenethiol	HMDB
2,6-Dimethylphenylthiol	HMDB
2,6-Dimethylthiophenol	HMDB
2,6-Thioxylenol	HMDB
2,6-Xylenethiol	HMDB
2,6-Xylenethiol, 8ci	HMDB
2,6-Xylyl mercaptan	HMDB
2-mercapto-m-Xylene	HMDB
FEMA 3666	HMDB
m-Xylene-2-thiol	HMDB

Chemical Formula

C₈H₁₀S

Average Molecular Weight

138.23

Monoisotopic Molecular Weight

138.05032101

IUPAC Name

2,6-dimethylbenzene-1-thiol

Traditional Name

2,6-dimethylbenzenethiol

CAS Registry Number

118-72-9

SMILES

CC1=CC=CC(C)=C1S

InChI Identifier

InChI=1S/C8H10S/c1-6-4-3-5-7(2)8(6)9/h3-5,9H,1-2H3

InChI Key

QCLJODDRBGKIRW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiophenols. Thiophenols are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Thiophenols

Sub Class

Not Available

Direct Parent

Thiophenols

Alternative Parents

Substituents

M-xylene
Xylene
Thiophenol
Monocyclic benzene moiety
Arylthiol
Hydrocarbon derivative
Organosulfur compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0032019)
Cell membrane (HMDB: HMDB0032019)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032019)

Source

Endogenous

Endogenous (HMDB: HMDB0032019)

Exogenous

Food

Food (HMDB: HMDB0032019)

Exogenous (HMDB: HMDB0032019)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032019)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	122.00 °C. @ 50.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	3.150	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.05	ALOGPS
logP	3.09	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.15 m³·mol⁻¹	ChemAxon
Polarizability	15.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.726	31661259
DarkChem	[M-H]-	125.046	31661259
DeepCCS	[M+H]+	127.921	30932474
DeepCCS	[M-H]-	124.914	30932474
DeepCCS	[M-2H]-	161.643	30932474
DeepCCS	[M+Na]+	136.678	30932474
AllCCS	[M+H]+	123.3	32859911
AllCCS	[M+H-H2O]+	118.5	32859911
AllCCS	[M+NH4]+	127.7	32859911
AllCCS	[M+Na]+	129.0	32859911
AllCCS	[M-H]-	121.8	32859911
AllCCS	[M+Na-2H]-	123.8	32859911
AllCCS	[M+HCOO]-	126.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.22 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8108 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1544.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	496.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	327.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	173.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	553.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	605.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	133.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1153.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	425.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1290.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	479.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	362.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	118.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethylbenzenethiol	CC1=CC=CC(C)=C1S	1666.7	Standard polar	33892256
2,6-Dimethylbenzenethiol	CC1=CC=CC(C)=C1S	1145.3	Standard non polar	33892256
2,6-Dimethylbenzenethiol	CC1=CC=CC(C)=C1S	1206.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethylbenzenethiol,1TMS,isomer #1	CC1=CC=CC(C)=C1S[Si](C)(C)C	1385.2	Semi standard non polar	33892256
2,6-Dimethylbenzenethiol,1TMS,isomer #1	CC1=CC=CC(C)=C1S[Si](C)(C)C	1296.1	Standard non polar	33892256
2,6-Dimethylbenzenethiol,1TBDMS,isomer #1	CC1=CC=CC(C)=C1S[Si](C)(C)C(C)(C)C	1646.0	Semi standard non polar	33892256
2,6-Dimethylbenzenethiol,1TBDMS,isomer #1	CC1=CC=CC(C)=C1S[Si](C)(C)C(C)(C)C	1532.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylbenzenethiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-6900000000-50987d418accfff29901	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylbenzenethiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethylbenzenethiol 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 - 2,6-Dimethylbenzenethiol 10V, Positive-QTOF	splash10-000i-0900000000-e6f12618c23f1869f5bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 20V, Positive-QTOF	splash10-000i-1900000000-d2264a29d1a77a3d7d86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 40V, Positive-QTOF	splash10-0uxu-9100000000-c7a1820b799b64d425b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 10V, Negative-QTOF	splash10-000i-0900000000-d6f0fcf20e1c7ea97f80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 20V, Negative-QTOF	splash10-000i-0900000000-01423387d70e6e254981	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 40V, Negative-QTOF	splash10-000i-4900000000-33a0efd6d62e309fda24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 10V, Positive-QTOF	splash10-052r-0900000000-78974e8a02fe8112dd0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 20V, Positive-QTOF	splash10-0a4i-5900000000-7913aae41f9c0b40e9e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 40V, Positive-QTOF	splash10-00or-9300000000-85a4f1af00216724af89	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 10V, Negative-QTOF	splash10-000i-0900000000-b2ac18843ae69f673fdc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 20V, Negative-QTOF	splash10-000i-1900000000-a1cab1a3247d0f9c824f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethylbenzenethiol 40V, Negative-QTOF	splash10-00ri-4900000000-61ca6983b8240bb2e938	2021-09-23	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB008717

KNApSAcK ID

Not Available

Chemspider ID

55004

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61045

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037331

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,6-Dimethylbenzenethiol (HMDB0032019)

MOL for HMDB0032019 (2,6-Dimethylbenzenethiol)

3D MOL for HMDB0032019 (2,6-Dimethylbenzenethiol)

3D SDF for HMDB0032019 (2,6-Dimethylbenzenethiol)

3D-SDF for HMDB0032019 (2,6-Dimethylbenzenethiol)

PDB for HMDB0032019 (2,6-Dimethylbenzenethiol)

3D PDB for HMDB0032019 (2,6-Dimethylbenzenethiol)

SMILES for HMDB0032019 (2,6-Dimethylbenzenethiol)

INCHI for HMDB0032019 (2,6-Dimethylbenzenethiol)

Structure for HMDB0032019 (2,6-Dimethylbenzenethiol)

3D Structure for HMDB0032019 (2,6-Dimethylbenzenethiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra