(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanoic acid

• ChemBase ID: 128007
• Molecular Formular: C12H22O12
• Molecular Mass: 358.29588
• Monoisotopic Mass: 358.11112614
• SMILES: O[C@@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C(=O)O)O[C@@H]1CO
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@H](C(=O)O)O)O)O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O
• InChI: InChI=1S/C12H22O12/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h3-10,12-20H,1-2H2,(H,21,22)/t3-,4-,5+,6+,7-,8-,9-,10-,12+/m1/s1
• InChIKey: JYTUSYBCFIZPBE-AMTLMPIISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanoic acid
• IUPAC Traditional name: lactobionic acid
• Synonyms: Galactosylgluconic acid; Lactobionic acid; 4-O-β-D-Galactopyranosyl-D-gluconic acid; Lactobionic acid; 4-O-β-D-吡喃半乳糖基-D-葡萄糖酸; 乳糖酸

Database IDs

• CAS Number: 96-82-2
• EC Number: 202-538-3
• MDL Number: MFCD00078147
• Beilstein Number: 95054
• PubChem SID: 162222323; 24896313
• PubChem CID: 7314; 16219560
• Chemspider ID: 7040
• Wikipedia Title: Lactobionic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.2613704
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -7.400029
• LogD (pH = 7.4): -8.614589
• Log P: -5.18058
• Molar Refractivity: 70.6843 cm^3
• Polarizability: 29.630531 Å^3
• Polar Surface Area: 217.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Syrup
• Melting Point: 113-118 °C(lit.)
• Density: 1.791 g/mL
• Optical Rotation: [α]20/D +25°, c = 10 in H2O; [α]20/D +26±3°, 24 hr, c = 10% in H2O

Safety Information

• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Grade: purum
• Ignition Residue: ≤0.1%
• Loss on Drying: ≤5% loss on drying
• Empirical Formula (Hill Notation): C12H22O12

DETAILS

Sigma Aldrich - L2398

Application
Cell impermeant agent used for organ preservation
Biochem/physiol Actions
Reported to inhibit production of hydroxyl radicals.1 Cryptic inhibitor of matrix metalloproteinases (MMP).2 Resistant to dietary metabolism but stimulates intestinal calcium absorption in rat.3
Packaging
100 g in poly bottle

Sigma Aldrich - 153516

Packaging
25, 100 g in poly bottle
Application
Lactobionic acid, an α-hydroxyacid (AHA) with antioxidation activity, is used in the development of cosmeceuticals for skin. Lactobionic acid is used in the development of targeting drug delivery systems, such as microcapsules.