(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-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 155125
• Molecular Formular: C28H34O15
• Molecular Mass: 610.56056
• Monoisotopic Mass: 610.18977039
• 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(c(c1)O)OC)O)CO)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3O[C@@H](CC(=O)c3c(c2)O)c2ccc(c(c2)O)OC)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChIKey: ARGKVCXINMKCAZ-UZRWAPQLSA-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-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: neohesperidin
• Synonyms: (S)-4′-Methoxy-3′,5,7-trihydroxyflavanone-7-[2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside]; Neohesperidin

Database IDs

• CAS Number: 13241-33-3
• EC Number: 236-216-9
• MDL Number: MFCD16661259
• Beilstein Number: 74945
• PubChem SID: 162249263; 24897534
• PubChem CID: 442439

CALCULATED PROPERTIES

• Acid pKa: 9.513642
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -0.31459877
• LogD (pH = 7.4): -0.31786907
• Log P: -0.314557
• Molar Refractivity: 140.767 cm^3
• Polarizability: 56.677265 Å^3
• Polar Surface Area: 234.29 Å^2
• Rotatable Bonds: 7
• 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: 2-8°C

Product Information

• Purity: ≥90%; ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C28H34O15

DETAILS

Sigma Aldrich - N1887

Biochem/physiol Actions
Flavanone glycoside with neuroprotective and antioxidant properties.1 Does not inhibit oral carcinogenesis in a rat model unlike other citrus flavanones2, but does exert a protective effect against gastritis and gastric lesions.3
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N1887.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N1887.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 72141

Biochem/physiol Actions
Flavanone glycoside with neuroprotective and antioxidant properties.1 Does not inhibit oral carcinogenesis in a rat model unlike other citrus flavanones2, but does exert a protective effect against gastritis and gastric lesions.3