(5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

• ChemBase ID: 149677
• Molecular Formular: C9H12O6
• Molecular Mass: 216.18798
• Monoisotopic Mass: 216.0633881
• SMILES: CC1(OC[C@H](O1)[C@@H]1C(=C(C(=O)O1)O)O)C
• Canonical SMILES: O=C1O[C@@H](C(=C1O)O)[C@@H]1COC(O1)(C)C
• InChI: InChI=1S/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3/t4-,7+/m0/s1
• InChIKey: POXUQBFHDHCZAD-MHTLYPKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
• IUPAC Traditional name: (5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-5H-furan-2-one
• Synonyms: (+)-5,6-O-Isopropylidene-L-ascorbic acid; 5,6-Isopropylidene-L-ascorbic acid; 5,6-Isopropylidene-L-ascorbic acid; (+)-5,6-O-Isopropylidene-L-ascorbic acid; (+)-5,6-O-异亚丙基-L-抗坏血酸; 5,6-异亚丙基-L-抗坏血酸; 5,6-异亚丙基-L-抗坏血酸; (+)-5,6-O-异亚丙基-L-抗坏血酸

Database IDs

• CAS Number: 15042-01-0
• MDL Number: MFCD00010552
• Beilstein Number: 86893
• PubChem SID: 24858183; 162243840
• PubChem CID: 54691418

CALCULATED PROPERTIES

• Acid pKa: 4.5245724
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.2290365
• LogD (pH = 7.4): -3.000189
• Log P: -0.21113425
• Molar Refractivity: 49.2391 cm^3
• Polarizability: 19.215916 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 210 °C (dec.)(lit.); 217 °C (dec.)
• Optical Rotation: [α]19/D +25.3°, c = 1 in H2O; [α]20/D +10.5±1°, c = 5% in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (sum of enantiomers, HPLC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C9H12O6

DETAILS

Sigma Aldrich - 301361

Packaging
5 g in glass bottle

Sigma Aldrich - 59435

Other Notes
Starting material for the synthesis of 3,4-isopropylidene-L-threonic acid and derivatives by oxidative cleavage1,2; Preparation of L-isopropylidene-glycerol3,4