1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one dihydrate

• ChemBase ID: 133856
• Molecular Formular: C21H28O12
• Molecular Mass: 472.43982
• Monoisotopic Mass: 472.15807634
• SMILES: c1cc(ccc1CCC(=O)c1c(cc(cc1O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O.O.O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)cc(c2C(=O)CCc2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O.O.O
• InChI: InChI=1S/C21H24O10.2H2O/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10;;/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2;2*1H2/t16-,18-,19+,20-,21-;;/m1../s1
• InChIKey: XQWBNXSENPTIDY-YXMARJSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one dihydrate
• IUPAC Traditional name: phlorizin dihydrate
• Synonyms: 1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone; Phloretin 2′-β-D-glucopyranoside; Phloretin 2′-β-D-glucoside; Phlorizin dihydrate; Phloridzin dihydrate; 1-[2-(β-D-吡喃葡糖基氧)-4,6-二羟基苯基]-3-(4-羟基苯基)-1-丙酮; 根皮素2′-β-D-吡喃葡萄糖苷; 根皮素2′-β-D-葡萄糖苷; 根皮苷 二水合物; 弗罗利辛 二水合物

Database IDs

• CAS Number: 7061-54-3
• EC Number: 200-487-1
• MDL Number: MFCD00149438
• Beilstein Number: 66621
• PubChem SID: 24898413; 162228133; 24856580
• PubChem CID: 9912668

CALCULATED PROPERTIES

• Acid pKa: 7.8912544
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.97572434
• LogD (pH = 7.4): 0.8561777
• Log P: 0.9774724
• Molar Refractivity: 105.8517 cm^3
• Polarizability: 41.671455 Å^3
• Polar Surface Area: 177.14 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 113-114 °C(lit.)
• Optical Rotation: [α]20/D -50±2°, c = 3.2% in ethanol; [α]20/D -52°, c = 3 in ethanol

Safety Information

• RTECS: UC2080000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); ≥99% (HPLC); 99%
• Salt Data: 2 H2O
• Empirical Formula (Hill Notation): C21H24O10 · 2H2O
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - P3449

Features and Benefits
用于诱导实验性糖尿。
Other Notes
Dihydrochalcone glycoside found in apple tree

Sigma Aldrich - 274313

Features and Benefits
Used to induce experimental glycosuria.
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 79320

Features and Benefits
Used to induce experimental glycosuria.
Other Notes
Blocks reabsorption of glucose from kidney tubules producing glycosuria1