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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:33 UTC

Update Date

2023-02-21 17:20:36 UTC

HMDB ID

HMDB0031474

Secondary Accession Numbers

HMDB31474

Metabolite Identification

Common Name

1,4-Dithiane

Description

1,4-Dithiane, also known as p-dithiane or fema 3831, belongs to the class of organic compounds known as dithianes. Dithianes are compounds containing a dithiane moiety, which is composed of a cyclohexane core structure wherein two methylene units are replaced by sulfur centres. A dithiane that is cyclohexane in which the -CH2- units at positions 1 and 2 have been replaced by sulfur atoms. 1,4-Dithiane is possibly neutral. 1,4-Dithiane is a fishy, garlic, and onion tasting compound. 1,4-Dithiane has been detected, but not quantified, in garden tomato. This could make 1,4-dithiane a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Dithiacyclohexane	ChEBI
1,4-Dithian	ChEBI
Diethylene disulfide	ChEBI
p-Dithiane	ChEBI
Para-dithiane	ChEBI
Tetrahydro-1,4-dithiin	ChEBI
Diethylene disulphide	Generator
FEMA 3831	HMDB
P-Dithane	HMDB
P-Dithiane, 8ci	HMDB
tetrahydro-P-DithIIn	HMDB

Chemical Formula

C₄H₈S₂

Average Molecular Weight

120.236

Monoisotopic Molecular Weight

120.006741636

IUPAC Name

1,4-dithiane

Traditional Name

1,4-dithiane

CAS Registry Number

505-29-3

SMILES

C1CSCCS1

InChI Identifier

InChI=1S/C4H8S2/c1-2-6-4-3-5-1/h1-4H2

InChI Key

LOZWAPSEEHRYPG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dithianes. Dithianes are compounds containing a dithiane moiety, which is composed of a cyclohexane core structure wherein two methylene units are replaced by sulfur centres.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithianes

Sub Class

Not Available

Direct Parent

Dithianes

Alternative Parents

Substituents

1,4-dithiane
Dialkylthioether
Thioether
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dithiane (CHEBI:540 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031474)
Cytoplasm (HMDB: HMDB0031474)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031474)

Source

Endogenous

Endogenous (HMDB: HMDB0031474)

Plant

Plant (HMDB: HMDB0031474)

Exogenous

Food

Food (HMDB: HMDB0031474)

Vegetable

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Exogenous (HMDB: HMDB0031474)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031474)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	112 - 113 °C	Not Available
Boiling Point	199.00 to 200.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3 mg/mL at 25 °C	Not Available
LogP	0.77	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.11 g/L	ALOGPS
logP	1.58	ALOGPS
logP	1.07	ChemAxon
logS	-2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.66 m³·mol⁻¹	ChemAxon
Polarizability	12.72 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]+	120.844	31661259
DarkChem	[M-H]-	114.313	31661259
DeepCCS	[M+H]+	128.685	30932474
DeepCCS	[M-H]-	126.686	30932474
DeepCCS	[M-2H]-	162.163	30932474
DeepCCS	[M+Na]+	136.576	30932474
AllCCS	[M+H]+	120.2	32859911
AllCCS	[M+H-H2O]+	115.4	32859911
AllCCS	[M+NH4]+	124.7	32859911
AllCCS	[M+Na]+	126.0	32859911
AllCCS	[M-H]-	130.7	32859911
AllCCS	[M+Na-2H]-	134.5	32859911
AllCCS	[M+HCOO]-	138.7	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.	2.26 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6226 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	161.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2548.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	554.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	370.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	375.3 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	742.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	157.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1044.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	363.3 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	1310.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	699.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	478.6 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	243.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4-Dithiane	C1CSCCS1	1600.2	Standard polar	33892256
1,4-Dithiane	C1CSCCS1	1034.5	Standard non polar	33892256
1,4-Dithiane	C1CSCCS1	1074.2	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 - 1,4-Dithiane GC-MS (Non-derivatized) - 70eV, Positive	splash10-024i-9300000000-afe762657ad82266011c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4-Dithiane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03ka-9300000000-0978d614df57b538ee56	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 10V, Positive-QTOF	splash10-00di-0900000000-0ce731fe6810007b4f15	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 20V, Positive-QTOF	splash10-00fr-9300000000-3fba6cbe60c31cf3bf46	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 40V, Positive-QTOF	splash10-076v-9000000000-4d1c0ee7aad402cf59a3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 10V, Negative-QTOF	splash10-052f-9000000000-c28865dfc1d0d9da7313	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 20V, Negative-QTOF	splash10-0a4i-9000000000-43ad8e9531b71aa9c65a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 40V, Negative-QTOF	splash10-0a4i-9000000000-fec022fdefd7d660643f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 10V, Positive-QTOF	splash10-00di-2900000000-f6360d51a18a4c6afdc9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 20V, Positive-QTOF	splash10-08fu-9000000000-353e7a5581b54f0861ed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 40V, Positive-QTOF	splash10-06r2-9000000000-d8564ac1eae58fba7fb8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 10V, Negative-QTOF	splash10-0bt9-9000000000-8404ed77f5c28c489a9e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 20V, Negative-QTOF	splash10-0a4i-9000000000-f76d7dda1401c82cc54e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Dithiane 40V, Negative-QTOF	splash10-0bt9-9100000000-ea17998e365762b4dc1c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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
Extracellular

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

FDB008047

KNApSAcK ID

Not Available

Chemspider ID

10020

KEGG Compound ID

C01871

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10452

PDB ID

Not Available

ChEBI ID

540

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1107551

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 1,4-Dithiane (HMDB0031474)

MOL for HMDB0031474 (1,4-Dithiane)

3D MOL for HMDB0031474 (1,4-Dithiane)

3D SDF for HMDB0031474 (1,4-Dithiane)

3D-SDF for HMDB0031474 (1,4-Dithiane)

PDB for HMDB0031474 (1,4-Dithiane)

3D PDB for HMDB0031474 (1,4-Dithiane)

SMILES for HMDB0031474 (1,4-Dithiane)

INCHI for HMDB0031474 (1,4-Dithiane)

Structure for HMDB0031474 (1,4-Dithiane)

3D Structure for HMDB0031474 (1,4-Dithiane)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra