(4S,5S)-5-hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid

• ChemBase ID: 156547
• Molecular Formular: C6H10N2O3
• Molecular Mass: 158.1552
• Monoisotopic Mass: 158.06914219
• SMILES: CC1=N[C@@H]([C@H](CN1)O)C(=O)O
• Canonical SMILES: O[C@H]1CNC(=N[C@@H]1C(=O)O)C
• InChI: InChI=1S/C6H10N2O3/c1-3-7-2-4(9)5(8-3)6(10)11/h4-5,9H,2H2,1H3,(H,7,8)(H,10,11)/t4-,5-/m0/s1
• InChIKey: KIIBBJKLKFTNQO-WHFBIAKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S)-5-hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
• IUPAC Traditional name: hydroxyectoine
• Synonyms: THP(A); (4S,5S)-5-Hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid; Hydroxyectoine; (4S,5S)-5-羟基-2-甲基-1,4,5,6-四氢嘧啶-4-羧酸; 羟基四氢嘧啶

Database IDs

• CAS Number: 165542-15-4
• MDL Number: MFCD01863080
• PubChem SID: 24879269; 24886115; 162250684
• PubChem CID: 12011795

CALCULATED PROPERTIES

• Acid pKa: 2.4773216
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.2163727
• LogD (pH = 7.4): -3.2219028
• Log P: -3.2163017
• Molar Refractivity: 36.1398 cm^3
• Polarizability: 14.202519 Å^3
• Polar Surface Area: 81.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95% (HPLC); ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C6H10N2O3

DETAILS

Sigma Aldrich - 55243

Other Notes
Stabilizing effect against various stress factors; used e.g. in the expression of proteins1,2

Sigma Aldrich - 70709

Other Notes
Stabilizer for enzymes and biological macromolecules1,2,3