(2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid; 3-[(2R)-1-methylpyrrolidin-2-yl]pyridine

• ChemBase ID: 153516
• Molecular Formular: C30H32N2O8
• Molecular Mass: 548.58368
• Monoisotopic Mass: 548.21586599
• SMILES: Cc1ccc(cc1)C(=O)O[C@@H]([C@@H](C(=O)O)OC(=O)c1ccc(cc1)C)C(=O)O.CN1CCC[C@@H]1c1cccnc1
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)OC(=O)c1ccc(cc1)C)OC(=O)c1ccc(cc1)C.CN1CCC[C@@H]1c1cccnc1
• InChI: InChI=1S/C20H18O8.C10H14N2/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14;1-12-7-3-5-10(12)9-4-2-6-11-8-9/h3-10,15-16H,1-2H3,(H,21,22)(H,23,24);2,4,6,8,10H,3,5,7H2,1H3/t15-,16-;10-/m01/s1
• InChIKey: GEGPCGHEPLKDLY-CERGLLGESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid; 3-[(2R)-1-methylpyrrolidin-2-yl]pyridine
• IUPAC Traditional name: (-)-nicotine; (2S,3S)-2,3-bis(4-methylbenzoyloxy)butanedioic acid
• Synonyms: R(+)-3-(1-Methyl2-pyrrolidinyl)pyridinium (+)di-p-toluoyl tartrate; (+)-Nicotine (+)-di-p-toluoyltartrate salt

Database IDs

• CAS Number: 68935-27-3
• MDL Number: MFCD00079531
• PubChem SID: 162247655; 24278600
• PubChem CID: 15991598

CALCULATED PROPERTIES

• Acid pKa: 2.8210018
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.7829022
• LogD (pH = 7.4): -1.8656341
• Log P: 4.1886425
• Molar Refractivity: 95.9398 cm^3
• Polarizability: 37.12853 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble; H2O: soluble
• Apperance: white to off-white powder
• Optical Rotation: [α]25/D +94.2°, c = 0.9 in methanol(lit.)

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-36/37/38-40
• Safety Statements: 22-36-45
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C10H14N2 · C20H18O8

DETAILS

Sigma Aldrich - N9765

Biochem/physiol Actions
Less active enantiomer of naturally-occurring (-)-nicotine.