2-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl 2-methylprop-2-enoate

• ChemBase ID: 142928
• Molecular Formular: C12H20O8
• Molecular Mass: 292.2824
• Monoisotopic Mass: 292.1158176
• SMILES: CC(=C)C(=O)OCCOC1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1OC(OCCOC(=O)C(=C)C)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H20O8/c1-6(2)11(17)18-3-4-19-12-10(16)9(15)8(14)7(5-13)20-12/h7-10,12-16H,1,3-5H2,2H3/t7-,8-,9+,10-,12?/m1/s1
• InChIKey: KUQRLZZWFINMDP-BGNLRFAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl 2-methylprop-2-enoate
• IUPAC Traditional name: 2-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl 2-methylprop-2-enoate
• Synonyms: GEMA; Glycosyloxyethyl methacrylate solution; 糖基氧乙基甲基丙烯酸酯 溶液

Database IDs

• MDL Number: MFCD00085263
• PubChem SID: 24884433; 162237154
• PubChem CID: 3083177

CALCULATED PROPERTIES

• Acid pKa: 12.210874
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.1532125
• LogD (pH = 7.4): -1.1532192
• Log P: -1.1532124
• Molar Refractivity: 65.1232 cm^3
• Polarizability: 26.7444 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 13 °C; 55.4 °F
• Density: 0.808 g/mL at 25 °C
• Refractive Index: n20/D 1.366

Safety Information

• European Hazard Symbols: Flammable (F); Nature polluting (N); Harmful (Xn)
• UN Number: 1170
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-20/21/22-51/53-68/20/21/22
• Safety Statements: 16-36/37-61
• GHS Pictograms: GHS02; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H371-H411
• GHS Precautionary statements: P210-P260-P273
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2

Product Information

• Concentration: 5 % (w/v) in ethanol
• Linear Formula: (C6H11O5)OCH2CH2OCOC(=CH2)CH3

DETAILS

Sigma Aldrich - 659576

Application
Forms copolymer with butyl acrylate which acts as a pressure-sensitive biomedical adhesive.1,2
Monomer for hydrogels used in drug delivery.
Packaging
25 mL in glass bottle