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

• ChemBase ID: 155911
• Molecular Formular: C27H32O15
• Molecular Mass: 596.53398
• Monoisotopic Mass: 596.17412032
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)O[C@@H](CC2=O)c1ccc(c(c1)O)O)O)O)O)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2ccc(c(c2)O)O)O[C@@H]([C@H]1O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
• InChIKey: OMQADRGFMLGFJF-MNPJBKLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: eriocitrin
• Synonyms: (S)-3′,4′,5,7-Tetrahydroxyflavanone-7-[6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside]; Eriocitrin

Database IDs

• CAS Number: 13463-28-0
• EC Number: 236-668-7
• MDL Number: MFCD00017472
• Beilstein Number: 1304401
• PubChem SID: 162250049; 24869120
• PubChem CID: 83489

CALCULATED PROPERTIES

• Acid pKa: 9.119624
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -0.4605546
• LogD (pH = 7.4): -0.46862283
• Log P: -0.46045104
• Molar Refractivity: 136.2847 cm^3
• Polarizability: 54.79462 Å^3
• Polar Surface Area: 245.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C27H32O15

DETAILS

Sigma Aldrich - 45714

Biochem/physiol Actions
Flavone glycoside found in lemon. Administration prior to acute exercise helped to maintain the redox status of liver glutathione. Without eriocitrin, it shifts markedly toward oxidized form.1

Sigma Aldrich - 94113

Biochem/physiol Actions
Flavone glycoside found in lemon. Administration prior to acute exercise helped to maintain the redox status of liver glutathione. Without eriocitrin, it shifts markedly toward oxidized form.1