Methacrylic anhydride

Methacrylic anhydride
Names
	Preferred IUPAC name 2-Methylprop-2-enoic anhydride
	Other names Methacrylic anhydride
Identifiers
CAS Number	760-93-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	12434;
ECHA InfoCard	100.010.986
PubChem CID	12974;
UNII	N2RJR03340 ;
CompTox Dashboard (EPA)	DTXSID60862404 ;
	InChI InChI=1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3 Key: DCUFMVPCXCSVNP-UHFFFAOYSA-N; InChI=1/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3 Key: DCUFMVPCXCSVNP-UHFFFAOYAX;
	SMILES O=C(OC(=O)\C(=C)C)\C(=C)C;
Properties
Chemical formula	C8H10O3
Molar mass	154.165 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methacrylic anhydride is a liquid which reacts with water exothermically.^[1]

It can also react with hydroxyl- and amino-groups present in some organic compounds leading to covalent attachment of methacryloyl moieties. These functional groups could be successfully used either in subsequent polymerisation or reactions with thiols. For example, chitosan modified by methacryloylation exhibits better ability to adhere to mucosal surfaces (mucoadhesion) due to its reactivity with thiols groups present in cysteine domains of mucins ).^[2]

References

^ Methacrylic anhydride at www.chemicalbook.com.
^ Kolawole, Oluwadamilola M.; Lau, Wing Man; Khutoryanskiy, Vitaliy V. (2018-10-25). "Methacrylated chitosan as a polymer with enhanced mucoadhesive properties for transmucosal drug delivery" (PDF). International Journal of Pharmaceutics. 550 (1): 123–129. doi:10.1016/j.ijpharm.2018.08.034. ISSN 0378-5173. PMID 30130604. S2CID 52055140.

[1] Methacrylic anhydride at www.chemicalbook.com.

[2] Kolawole, Oluwadamilola M.; Lau, Wing Man; Khutoryanskiy, Vitaliy V. (2018-10-25). "Methacrylated chitosan as a polymer with enhanced mucoadhesive properties for transmucosal drug delivery" (PDF). International Journal of Pharmaceutics. 550 (1): 123–129. doi:10.1016/j.ijpharm.2018.08.034. ISSN 0378-5173. PMID 30130604. S2CID 52055140.

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