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

• ChemBase ID: 133413
• Molecular Formular: C6H10N2O2
• Molecular Mass: 142.1558
• Monoisotopic Mass: 142.07422757
• SMILES: CC1=N[C@@H](CCN1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1CCNC(=N1)C
• InChI: InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1
• InChIKey: WQXNXVUDBPYKBA-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
• IUPAC Traditional name: ectoine
• Synonyms: Thp(B); Ectoine; (S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid; (S)-2-甲基-1,4,5,6-四氢嘧啶-4-羧酸; 四氢嘧啶

Database IDs

• CAS Number: 96702-03-3
• EC Number: 431-910-1
• MDL Number: MFCD03419286
• Beilstein Number: 7288977
• PubChem SID: 162227690; 24894465; 24887879
• PubChem CID: 126041

CALCULATED PROPERTIES

• Acid pKa: 2.7460206
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.5263588
• LogD (pH = 7.4): -2.5260491
• Log P: -2.525868
• Molar Refractivity: 35.0427 cm^3
• Polarizability: 13.507389 Å^3
• Polar Surface Area: 61.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (HPLC); ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C6H10N2O2

DETAILS

Sigma Aldrich - E2271

Biochem/physiol Actions
An osmoprotectant in a wide variety of microorganisms including heterotrophic, halophilic bacteria and non-halophilic bacteria such as Streptomyces species and E.coli. It also exerts protective effects in E.coli during drying and storage.

Sigma Aldrich - 81619

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