(2-Hydroxyethyl) dimethylsulfoxonium chloride

(2-Hydroxyethyl) dimethylsulfoxonium chloride
Identifiers
CAS Number	334026-23-2 ;
3D model (JSmol)	Interactive image;
	InChI InChI=1S/C4H11O2S.ClH/c1-7(2,6)4-3-5;/h5H,3-4H2,1-2H3;1H/q+1;/p-1 Key: PLNZFRZUPJUJMX-UHFFFAOYSA-M;
	SMILES OCC[S+](=O)(C)C.[Cl-];
Properties
Chemical formula	C4H11ClO2S
Molar mass	158.64 g·mol−1
Related compounds
Related compounds	Choline
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

(2-Hydroxyethyl) dimethylsulfoxonium chloride is an organic salt found in sea chervils and sea sponges that causes the Dogger Bank itch.^[1]

Properties

(2-Hydroxyethyl) dimethylsulfoxonium chloride is colourless. It dissolves in dioxane, methanol, chloroform or water.^[2]

(2-Hydroxyethyl) dimethylsulfoxonium chloride is a salt, with a sulfur atom having a positive charge. Attached to the sulfur are two methyl groups, and oxygen atom, and an ethoxy group attached at the number 2 carbon.^[2]

As a solid, its crystal structure is orthorhombic, with unit cell dimensions a = 11.033, b = 13.847 and c = 9.871 Å. The space group is Pbca. There are eight formulae per unit cell. The density is 1.251 g/cm³.^[2]

Natural occurrence

(2-Hydroxyethyl) dimethylsulfoxonium chloride has been discovered so far in invertebrate animals in the genus Alcyonidium and a single species of sea sponge.^[3]

References

^ Carle, Joergen S.; Christophersen, Carsten (July 1980). "Dogger Bank itch. The allergen is (2-hydroxyethyl)dimethylsulfoxonium ion". Journal of the American Chemical Society. 102 (15): 5107–5108. doi:10.1021/ja00535a053.
^ ^a ^b ^c Warabi, Kaoru; Nakao, Yoichi; Matsunaga, Shigeki; Fukuyama, Tohru; Kan, Toshiyuki; Yokoshima, Satoshi; Fusetani, Nobuhiro (January 2001). "Dogger Bank Itch revisited: isolation of (2-hydroxyethyl) dimethylsulfoxonium chloride as a cytotoxic constituent from the marine sponge Theonella aff. mirabilis". Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology. 128 (1): 27–30. doi:10.1016/S1096-4959(00)00316-X. PMID 11163301.
^ Fusetani, Nobuhiro (2009). "Marine toxins: An overview". Marine Toxins as Research Tools. Progress in Molecular and Subcellular Biology. Vol. 46. pp. 1–44. Bibcode:2009mtrt.book....1F. doi:10.1007/978-3-540-87895-7_1. ISBN 978-3-540-87892-6. PMID 19184583.

[1] Carle, Joergen S.; Christophersen, Carsten (July 1980). "Dogger Bank itch. The allergen is (2-hydroxyethyl)dimethylsulfoxonium ion". Journal of the American Chemical Society. 102 (15): 5107–5108. doi:10.1021/ja00535a053.

[warabi-2] Warabi, Kaoru; Nakao, Yoichi; Matsunaga, Shigeki; Fukuyama, Tohru; Kan, Toshiyuki; Yokoshima, Satoshi; Fusetani, Nobuhiro (January 2001). "Dogger Bank Itch revisited: isolation of (2-hydroxyethyl) dimethylsulfoxonium chloride as a cytotoxic constituent from the marine sponge Theonella aff. mirabilis". Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology. 128 (1): 27–30. doi:10.1016/S1096-4959(00)00316-X. PMID 11163301.

[3] Fusetani, Nobuhiro (2009). "Marine toxins: An overview". Marine Toxins as Research Tools. Progress in Molecular and Subcellular Biology. Vol. 46. pp. 1–44. Bibcode:2009mtrt.book....1F. doi:10.1007/978-3-540-87895-7_1. ISBN 978-3-540-87892-6. PMID 19184583.

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