(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 127292
• Molecular Formular: C15H12O6
• Molecular Mass: 288.25218
• Monoisotopic Mass: 288.0633881
• SMILES: O=C1c2c(O[C@H](c3ccc(O)c(O)c3)C1)cc(O)cc2O
• Canonical SMILES: Oc1cc2O[C@@H](CC(=O)c2c(c1)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2/t13-/m0/s1
• InChIKey: SBHXYTNGIZCORC-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: eriodictyol
• Synonyms: Eriodictiol; Eriodictyol; (S)-3′,4′,5,7-Tetrahydroxyflavanone; Eriodictyol

Database IDs

• CAS Number: 552-58-9
• EC Number: 209-016-4
• MDL Number: MFCD00135890
• Beilstein Number: 5104930
• PubChem SID: 24886695; 162221613
• PubChem CID: 440735
• Chemspider ID: 389606
• Unique Ingredient Identifier: Q520486B8Y
• Wikipedia Title: Eriodictyol

CALCULATED PROPERTIES

• Acid pKa: 7.847641
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.5296102
• LogD (pH = 7.4): 2.3976264
• Log P: 2.5315428
• Molar Refractivity: 73.2707 cm^3
• Polarizability: 27.938951 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• 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

Pharmacology Properties

• Gene Information: mouse ... Hexa(15211)

Product Information

• Purity: ≥95.0% (HPLC); 98.0
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C15H12O6

DETAILS

Sigma Aldrich - 74565

Biochem/physiol Actions
The flavanone eriodictyol is a metabolite in the flavonoid biosynthesis pathway. Eriodictyol has anti-inflammatory and antioxidant activities1 and taste-modifying properties; it is extracted from plants such as Eriodictyon californicum2, the twigs of Millettia duchesnei,3 in Eupatorium arnottianum,4 lemons and as glycoside in rose hips (Rosa canina).5