(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one hydrate

• ChemBase ID: 146751
• Molecular Formular: C27H34O15
• Molecular Mass: 598.54986
• Monoisotopic Mass: 598.18977039
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1Oc1cc(c2c(c1)O[C@@H](CC2=O)c1ccc(cc1)O)O)CO)O)O)O)O)O.O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O.O
• InChI: InChI=1S/C27H32O14.H2O/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11;/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3;1H2/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+;/m0./s1
• InChIKey: CPNHAWBPPPWRLN-OSSFAINNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one hydrate
• IUPAC Traditional name: naringin hydrate
• Synonyms: Naringin hydrate

Database IDs

• CAS Number: 132203-74-8
• MDL Number: MFCD00149445
• PubChem SID: 162240943; 24853336
• PubChem CID: 6419948

CALCULATED PROPERTIES

• Acid pKa: 9.315869
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -0.15695165
• LogD (pH = 7.4): -0.16210435
• Log P: -0.15688573
• Molar Refractivity: 134.3038 cm^3
• Polarizability: 54.11746 Å^3
• Polar Surface Area: 225.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 166 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -91°, c = 1 in ethanol

Safety Information

• German water hazard class: 3

Product Information

• Grade: technical grade
• Empirical Formula (Hill Notation): C27H32O14 · xH2O

DETAILS

Sigma Aldrich - 222496

Biochem/physiol Actions
Antioxidant and anti-inflammatory found in citrus fruits.
Packaging
25 g in glass bottle