NP-MRD: Showing NP-Card for 1,4-Dithiane (NP0000782)

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Record Information

Version

1.0

Created at

2012-09-11 17:43:33 UTC

Updated at

2021-08-19 23:58:28 UTC

NP-MRD ID

NP0000782

Secondary Accession Numbers

None

Natural Product 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 A dithiane that is cyclohexane in which the -CH2- units at positions 1 and 2 have been replaced by sulfur atoms. 1,4-Dithiane is possibly neutral. 1,4-Dithiane is a fishy, garlic, and onion tasting compound. 1,4-Dithiane has been detected, but not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

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.037  -1.283   0.136  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.689   0.095   0.179  0.00  0.00           C+0
HETATM    3  S   UNK     0       0.533   1.345   0.708  0.00  0.00           S+0
HETATM    4  C   UNK     0      -1.054   1.287  -0.096  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.608  -0.107  -0.264  0.00  0.00           C+0
HETATM    6  S   UNK     0      -0.408  -1.267  -0.929  0.00  0.00           S+0
HETATM    7  H   UNK     0       0.744  -1.515   1.177  0.00  0.00           H+0
HETATM    8  H   UNK     0       1.769  -2.017  -0.240  0.00  0.00           H+0
HETATM    9  H   UNK     0       2.226   0.332  -0.758  0.00  0.00           H+0
HETATM   10  H   UNK     0       2.497   0.005   0.964  0.00  0.00           H+0
HETATM   11  H   UNK     0      -1.795   1.831   0.562  0.00  0.00           H+0
HETATM   12  H   UNK     0      -1.077   1.790  -1.096  0.00  0.00           H+0
HETATM   13  H   UNK     0      -2.434  -0.018  -1.027  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.117  -0.479   0.655  0.00  0.00           H+0
CONECT    1    2    6    7    8                                             
CONECT    2    1    3    9   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   11   12                                             
CONECT    5    4    6   13   14                                             
CONECT    6    5    1                                                       
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11    4                                                            
CONECT   12    4                                                            
CONECT   13    5                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

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 Mass

120.2360 Da

Monoisotopic Mass

120.00674 Da

IUPAC Name

1,4-dithiane

Traditional Name

1,4-dithiane

CAS Registry Number

505-29-3

SMILES

[H]C1([H])SC([H])([H])C([H])([H])SC1([H])[H]

InChI Identifier

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

InChI Key

LOZWAPSEEHRYPG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0031474

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1107551

References

General References

Peloquin AJ, Alapati S, McMillen CD, Hanks TW, Pennington WT: Polymorphism, Halogen Bonding, and Chalcogen Bonding in the Diiodine Adducts of 1,3- and 1,4-Dithiane. Molecules. 2021 Aug 17;26(16). pii: molecules26164985. doi: 10.3390/molecules26164985. [PubMed:34443571 ]
Peloquin AJ, McCollum JM, McMillen CD, Pennington WT: Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents. Angew Chem Int Ed Engl. 2021 Oct 11;60(42):22983-22989. doi: 10.1002/anie.202110520. Epub 2021 Sep 12. [PubMed:34415645 ]
Abe K, Myoda T, Nojima S: Identification and Characterization of Sulfur Heterocyclic Compounds That Contribute to the Acidic Odor of Aged Garlic Extract. J Agric Food Chem. 2021 Jan 27;69(3):1020-1026. doi: 10.1021/acs.jafc.0c06634. Epub 2021 Jan 15. [PubMed:33448852 ]
Hemstrom P, Holmgren KH, Hammarstrom BE, Larsson A, Ostin A: Identification and toxicological evaluation of cyclic sulfonium ion degradation products of sulphur mustard. Mar Environ Res. 2020 Dec;162:105047. doi: 10.1016/j.marenvres.2020.105047. Epub 2020 Aug 7. [PubMed:32827946 ]
Wang MX, Liu J, Liu Z, Wang Y, Yang QQ, Shan W, Deng YH, Shao Z: Enantioselective synthesis of chiral alpha-alkynylated thiazolidones by tandem S-addition/acetalization of alkynyl imines. Org Biomol Chem. 2020 Apr 29;18(16):3117-3124. doi: 10.1039/d0ob00365d. [PubMed:32253417 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for 1,4-Dithiane (NP0000782)

MOL for NP0000782 (1,4-Dithiane)

3D MOL for NP0000782 (1,4-Dithiane)

3D SDF for NP0000782 (1,4-Dithiane)

3D-SDF for NP0000782 (1,4-Dithiane)

PDB for NP0000782 (1,4-Dithiane)

3D PDB for NP0000782 (1,4-Dithiane)

SMILES for NP0000782 (1,4-Dithiane)

INCHI for NP0000782 (1,4-Dithiane)

Structure for NP0000782 (1,4-Dithiane)

3D Structure for NP0000782 (1,4-Dithiane)