4-methyl-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one

• ChemBase ID: 105953
• Molecular Formular: C16H18O8
• Molecular Mass: 338.30932
• Monoisotopic Mass: 338.10016754
• SMILES: O=c1oc2cc(O[C@@H]3O[C@@H]([C@H](O)[C@H](O)[C@H]3O)CO)ccc2c(c1)C
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C16H18O8/c1-7-4-12(18)23-10-5-8(2-3-9(7)10)22-16-15(21)14(20)13(19)11(6-17)24-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13+,14+,15-,16-/m1/s1
• InChIKey: YUDPTGPSBJVHCN-DZQJYWQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methyl-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
• IUPAC Traditional name: 4-methyl-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one
• Synonyms: MUG; MUGA; 4-Methylumbelliferyl β-D-galactopyranoside; 4-Methylumbelliferyl-β-D-galactopyranoside; 4-METHYLUMBELLIFERYL β-D-GALACTOSIDE; 4-Methylumbelliferyl-beta-D-galactopyranoside; 4-甲基-7-氧香豆素-β-D-吡喃半乳糖苷

Database IDs

• CAS Number: 6160-78-7
• EC Number: 228-185-5
• MDL Number: MFCD00036773
• Beilstein Number: 94673
• PubChem SID: 24896676; 162087677
• PubChem CID: 93577

CALCULATED PROPERTIES

• Acid pKa: 12.20014
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.4888793
• LogD (pH = 7.4): -0.48888606
• Log P: -0.4888792
• Molar Refractivity: 79.9559 cm^3
• Polarizability: 31.877827 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 232-236°C; 258-263 °C (dec.); ca 260°C dec.
• Optical Rotation: [α]20/D -64±2°, c = 1% in pyridine; -64 (c=1 in pyridine, 24h)
• Fluorescence: λex 360 nm; λem 447 nm in 0.05 M phosphate buffer pH 7.8 (β-Galactosidase)

Safety Information

• Storage Condition: 0°C
• Storage Warning: Light Sensitive
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); ≥99% (TLC); 98%
• Grade: for fluorescence
• Impurities: ≤1% water
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C16H18O8
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02195322

Crystalline
Purity: 98% min.

Sigma Aldrich - M1633

Substrates
Fluorescent substrate for β-galactosidase.

Sigma Aldrich - 69590

Application
Suitable as a fluorogenic substrate for β-Galactosidase (EC 3.2.1.23)
Other Notes
Substrate for β-galactosidase1