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

• ChemBase ID: 175116
• Molecular Formular: C30H32N2O8
• Molecular Mass: 548.58368
• Monoisotopic Mass: 548.21586599
• SMILES: c1cncc(c1)[C@@H]1CCCN1C.c1(ccc(cc1)C(=O)O[C@H]([C@@H](OC(=O)c1ccc(cc1)C)C(=O)O)C(=O)O)C
• 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-/m10/s1
• InChIKey: GEGPCGHEPLKDLY-VZOQACJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-bis(4-methylbenzoyloxy)butanedioic acid; 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• IUPAC Traditional name: (2R,3R)-2,3-bis(4-methylbenzoyloxy)butanedioic acid; nicoderm CQ
• Synonyms: S-(-)-3-(1-Methyl-2-pyrrolidinyl)pyridinium (+)-Di-p-toluoyl Tartrate; S-(-)-Nicotine Di-p-Toluoyl-D-Tartrate Salt

Database IDs

• CAS Number: 68935-26-2
• PubChem SID: 164231026
• PubChem CID: 71751008

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 (25 mg/ 0.5 ml yields clear solution in Ethanol); Water
• Apperance: White Powder
• Melting Point: 148-149°C dec.

DETAILS

Toronto Research Chemicals - N422001

(-)-Nicotine Di-p-Toluoyl-D-Tartrate is used in the synthesis of optically pure Nicotine.

REFERENCES

• Aceto, M.D., et al.: J. Med. Chem., 22, 174 (1979)