Dimethyl sulfone

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Structural formula
Structure of dimethyl sulfone
General
Surname Dimethyl sulfone
other names
  • Methylsulfonylmethane
  • Sulfonyl bismethane
  • DIMETHYL SULPHONE ( INCI )
Molecular formula C 2 H 6 O 2 S
Brief description

colorless crystals

External identifiers / databases
CAS number 67-71-0
EC number 200-665-9
ECHA InfoCard 100,000,605
PubChem 6213
ChemSpider 5978
DrugBank DB14090
Wikidata Q423842
properties
Molar mass 94.13 g · mol -1
Physical state

firmly

density

1.17 g cm −3

Melting point

107-110 ° C

boiling point

238 ° C

solubility

moderate in water (150 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

> 5000 mg kg −1 ( LD 50 ,  rat ,  oral )

Thermodynamic properties
ΔH f 0

−450.1 kJ / mol

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dimethyl sulfone is the simplest organic sulfur compound from the class of sulfones . It differs from the solvent dimethyl sulfoxide in that it has an additional oxygen atom attached to the sulfur atom.

Occurrence

Dimethyl sulfone occurs in many animal and plant organisms and is also part of the human diet. Comparatively high concentrations are found in cow's milk (3.3  ppm ) and coffee (1.6 ppm).

presentation

Dimethyl sulfone representation

Like all organic sulfones, dimethyl sulfone can be produced by oxidizing dimethyl sulfide with hydrogen peroxide H 2 O 2 . Dimethyl sulfoxide is formed as an intermediate product .

properties

Chemical properties

Pure dimethyl sulfone forms colorless, odorless, water-soluble and slightly bitter-tasting crystals. The melting point was determined at 109 ° C with a melting enthalpy of 18.28 kJ mol −1 . The heat of vaporization at the boiling point is 56.0 kJ mol −1 . The compound is flammable, but with a flash point of 143 ° C it is difficult to ignite.
Similar to dimethyl sulfoxide, dimethyl sulfone is weakly CH-azide, so that it can be replaced by strong bases such as B. butyllithium can be deprotonated.

Pharmacological properties

In an animal experiment with artificially induced malignant tumors of the large intestine and breast, a delayed outbreak of the disease was observed when dimethyl sulfone was administered. In 2012, researchers from the Korean University of Konkuk found that dimethyl sulfone had an inhibitory effect on human breast cancer cells . In both in-vitro and in-vivo experiments, they observed a regulatory effect on STAT 3, STAT5b, IGF- 1R, IGF-1 and VEGF , which are involved in tumor development, tumor growth and metastasis.

Biological importance

Similar to the representation in the laboratory, dimethyl sulfone is also the product of the metabolism of dimethyl sulfoxide in the organism of mammals . This is oxidized to dimethyl sulfone in the liver via the cytochrome P450 enzyme system and then excreted in the urine .

Use as a dietary supplement

Dimethyl sulfone, usually under the name methyl sulfonyl methane (MSM), is offered as a dietary supplement for humans and animals, especially horses. It is supposed to compensate for a lack of sulfur in the organism.

In the advice literature, the substance is assigned a variety of different effects, for example promoting collagen formation , strengthening the immune system or supporting the intestinal function. In a statement by the European Food Safety Authority (EFSA), these and other alleged health effects have not been scientifically proven, so the effects attributed to MSM should not be advertised.

According to the Öko-Test magazine , the additional intake of sulfur in the form of dimethyl sulfone does not make sense, since there is no malnutrition of proteins in Germany, which are the main source of sulfur in food. Because of the protein-rich diet in Western countries, a “sulfur deficiency” has not yet been described. Health claims for MSM in food supplements are not permitted under the Health Claims Regulation . The consumer advice center warns and points out that MSM is neither a remedy nor an approved drug. In addition, side effects are not known from long-term use.

literature

  • Earl L. Mindell: The MSM Miracle: Enhance your health with organic sulfur. Keats Publishing, Connecticut, USA 1997, ISBN 0-87983-841-8 .
  • Stanley W. Jacob: The current Status of MSM in Medicine. In: At Acad Med Prev. 1983.
  • VL Richmond: Incorporation of MSM into Guinea Pig Serum Proteins. In: Life Science. 39, 1986, pp. 263-268.

Individual evidence

  1. ↑ Entry on DIMETHYL SULFONE in the CosIng database of the EU Commission, accessed on June 27, 2020.
  2. ↑ a b c d e Entry for CAS no. 67-71-0 in the GESTIS substance database of the IFA , accessed on October 13, 2016(JavaScript required) .
  3. ↑ a b c d data sheet dimethyl sulfone (PDF) from Merck , accessed on January 19, 2011.
  4. ↑ Entry on dimethyl sulfone. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
  5. ↑ a b Data sheet Dimethyl sulfone, 98% from Sigma-Aldrich , accessed on February 13, 2013 ( PDF ).
  6. ↑ Entry on Dimethyl sulfone in the ChemIDplus database of the United States National Library of Medicine (NLM)
  7. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-22.
  8. ↑ ES Domalski, ED Hearing: Heat Capacities and Entropies of Organic Compounds in the Condensed phase. Volume III. In: J. Phys. Chem. Ref. Data . 25, 1996, pp. 1-525, doi: 10.1063 / 1.555985 .
  9. ↑ RM Stephenson, S. Malanowski: Handbook of the Thermodynamics of Organic Compounds. Springer 1987, ISBN 94-010-7923-4 , doi: 10.1007 / 978-94-009-3173-2 .
  10. ↑ Eun Joung Lim et al .: Methylsulfonylmethane suppresses breast cancer growth by down-regulating STAT3 and STAT5b pathways . In: PloS One . tape 7 , no. 4 , 2012, p. e33361 , doi : 10.1371 / journal.pone.0033361 , PMID 22485142 , PMC 3317666 (free full text).
  11. ↑ a b Scientific Opinion on the substantiation of health claims related to methylsulphonylmethane (MSM) and contribution to normal collagen formation (ID 353, 388, 389, 394, 1695, 1741, 1874), maintenance of normal hair (ID 353, 1741, 1874), maintenance of normal nails (ID 1695, 1741, 1874), maintenance of normal acid-base balance (ID 387), “strengthens the immune system function” (ID 390), maintenance of normal bowel function (ID 391), contribution to the normal cysteine ​​synthesis (ID 392) and “vitamin production needed for correct function of metabolism” (ID 393) pursuant to Article 13 (1) of Regulation (EC) No 1924/2006 . In: EFSA Journal . tape 8 , no. 10 , October 19, 2010, p. 1746 , doi : 10.2903 / j.efsa.2010.1746 (English).
  12. ↑ Remedies for joint problems. Flexible is different. In: Öko-Test . May 2009.
  13. ↑ MSM - new miracle drug from the USA . In: DAZ.online . April 15, 2001 ( deutsche-apotheker-zeitung.de [accessed on September 23, 2018]).
  14. ↑ EU Register on Nutrition and Health Claims
  15. ↑ MSM - does sulfur therapy help with osteoarthritis? | Consumer Center.de. March 3, 2020, accessed March 17, 2020 .