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

• ChemBase ID: 129041
• Molecular Formular: C28H34O14
• Molecular Mass: 594.56116
• Monoisotopic Mass: 594.19485577
• 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(=O)C[C@H](Oc2c1)c1ccc(cc1)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(cc2)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/C28H34O14/c1-11-21(32)23(34)25(36)27(38-11)42-26-24(35)22(33)19(10-29)41-28(26)39-14-7-15(30)20-16(31)9-17(40-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-30,32-36H,9-10H2,1-2H3/t11-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChIKey: NLAWPKPYBMEWIR-SKYQDXIQSA-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-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: poncirin
• Synonyms: Isosakuranetin-7-neohesperidoside; Poncirin; (S)-5,7-Dihydroxy-4′-methoxyflavanone-7-[2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside]; Poncirin

Database IDs

• CAS Number: 14941-08-3
• EC Number: 239-020-1
• MDL Number: MFCD00017476
• Beilstein Number: 74301
• PubChem SID: 162223342; 24887785
• PubChem CID: 442456
• CHEMBL: 451050
• Wikipedia Title: Poncirin

CALCULATED PROPERTIES

• Acid pKa: 9.836656
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -0.011011509
• LogD (pH = 7.4): -0.01256503
• Log P: -0.010991666
• Molar Refractivity: 138.7861 cm^3
• Polarizability: 56.003212 Å^3
• Polar Surface Area: 214.06 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

Product Information

• Purity: ≥96.0% (HPLC)
• Empirical Formula (Hill Notation): C28H34O14

DETAILS

Sigma Aldrich - 81467

Application
Poncirin (with other flavonoids of the bitter orange) was tested as a control agent for mosquito infestation, and was found to be larvacidal, to repel females from egg-laying on treated water, and to repel insects from biting topically treated human volunteers.1