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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-09-13 08:28:37 UTC |
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Update Date | 2020-10-09 21:03:54 UTC |
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HMDB ID | HMDB0004983 |
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Secondary Accession Numbers | - HMDB0006702
- HMDB04983
- HMDB06702
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Metabolite Identification |
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Common Name | Dimethyl sulfone |
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Description | Dimethyl sulfone, also known as sulfonylbismethane or lignisul MSM, belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms. DMSO2 reflects its close chemical relationship to dimethyl sulfoxide (DMSO), which differs only in the oxidation state of the sulfur atom. Dimethyl sulfone is possibly neutral. Dimethyl sulfone exists in all living organisms, ranging from bacteria to humans. DMSO2 is the primary metabolite of DMSO in humans, and it shares some of the properties of DMSO. Dimethyl sulfone is a burnt and sulfurous tasting compound. Outside of the human body, Dimethyl sulfone is found, on average, in the highest concentration within milk (cow). Dimethyl sulfone has also been detected, but not quantified in, asparagus and guava. This could make dimethyl sulfone a potential biomarker for the consumption of these foods. Dimethyl sulfone can be found in Afipia (Wikipedia ). It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages. Dimethyl sulfone (DMSO2) or Dimethyl sulfone (MSM), is an organic sulfur compound belonging to a class of chemicals known as sulfones. It derives from dietary sources, from intestinal bacterial metabolism and from human endogenous methanethiol metabolism. Dimethyl sulfone is a metabolite occurring in plasma and CSF of normal human. |
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Structure | |
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Synonyms | Value | Source |
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Dimethyl sulphone | ChEBI | Methylsulfonylmethane | ChEBI | Sulfonylbismethane | ChEBI | Sulphonylbismethane | ChEBI | Methylsulphonylmethane | Generator | (Methylsulfonyl)methane | HMDB | Dimethylsulfone | HMDB | Lignisul MSM | HMDB | Methyl sulfone | HMDB | Opti MSM | HMDB | Sulfonylbis-methane | HMDB | Methyl sulfonmethane | HMDB | Dimethyl sulfone, 13C-labeled | HMDB | Sulphonyldimethane | HMDB | Dimethyl sulfone | ChEBI |
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Chemical Formula | C2H6O2S |
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Average Molecular Weight | 94.133 |
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Monoisotopic Molecular Weight | 94.008850126 |
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IUPAC Name | methanesulfonylmethane |
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Traditional Name | methylsulfonylmethane |
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CAS Registry Number | 67-71-0 |
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SMILES | CS(C)(=O)=O |
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InChI Identifier | InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3 |
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InChI Key | HHVIBTZHLRERCL-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organosulfur compounds |
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Class | Sulfonyls |
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Sub Class | Sulfones |
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Direct Parent | Sulfones |
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Alternative Parents | |
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Substituents | - Sulfone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 109 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -1.41 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-9000000000-3e72edc8bd8e168298a0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0002-9000000000-9896ec507f104ada81f3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014i-9000000000-aad0ad2e46e9a93df295 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-9000000000-8cb5ee5ae152833c1e84 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-fb26633c75e592809868 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-3a6db80e12370ab204a9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-002b-9000000000-c5c35fbdd4193d0ece0d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-9000000000-c0a7fe921fa7e601fb70 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-113ab821ffdae95a6086 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00fu-9000000000-2ef5cb880f6a43bd9df3 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Saliva
- Urine
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 1.5-16.1 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 8.8 +/- 7.3 uM | Adult (>18 years old) | Not Specified | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.0 +/- 1.0 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 11.3 +/- 6.2 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 13.53 +/- 5.14 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 8.0 (1.3-49.0) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 4.6 (2.5-7.5) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 11.371 +/- 7.16 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 37.5 - 42.5 uM | Adult (>18 years old) | Both | Methionine adenosyltransferase (MAT) I/III deficiency | | details | Blood | Detected and Quantified | 5.06 (3.56) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 4.78 (2.73) uM | Adult (>18 years old) | Female | Pregnancy | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 574.0 uM | Adult (>18 years old) | Both | Methionine adenosyltransferase (MAT) I/III deficiency | | details | Urine | Detected and Quantified | 10.047 +/- 14.963 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details |
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Associated Disorders and Diseases |
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Disease References | Pregnancy |
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- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Methionine adenosyltransferase deficiency |
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- Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6. [PubMed:15996001 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | - 250850 (Methionine adenosyltransferase deficiency)
- 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB006725 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 5978 |
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KEGG Compound ID | C11142 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Methylsulfonylmethane |
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METLIN ID | 7236 |
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PubChem Compound | 6213 |
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PDB ID | Not Available |
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ChEBI ID | 9349 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000464 |
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References |
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Synthesis Reference | Douglas, Thomas B. Heats of formation of liquid methyl suffoxide and crystalline methyl sulfone at 18° Journal of the American Chemical Society (1946), 68 1072-6. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Rogovin JL: Accumulation of methylsulfonylmethane in the human brain: identification by multinuclear magnetic resonance spectroscopy. Toxicol Lett. 2002 Mar 28;129(3):263; author reply 265. [PubMed:11888710 ]
- Rose SE, Chalk JB, Galloway GJ, Doddrell DM: Detection of dimethyl sulfone in the human brain by in vivo proton magnetic resonance spectroscopy. Magn Reson Imaging. 2000 Jan;18(1):95-8. [PubMed:10642107 ]
- Lin A, Nguy CH, Shic F, Ross BD: Accumulation of methylsulfonylmethane in the human brain: identification by multinuclear magnetic resonance spectroscopy. Toxicol Lett. 2001 Sep 15;123(2-3):169-77. [PubMed:11641045 ]
- Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6. [PubMed:15996001 ]
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