Isorhamnetin 3-O-neohesperidoside
Basic information
- CAS
55033-90-4- Standard SMILES
COc1cc(-c2oc3cc(O)cc(O)c3c(=O)c2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)ccc1O- InChIKey
QHLKSZBFIJJREC-SPSUIZEHSA-N- Molecular formula
- C28H32O16
- Average molar mass
- 624.5 g/mol
- Monoisotopic mass
- 624.16903493
Overview
Isorhamnetin-3-O-nehesperidine is a glycoside and a member of flavonoids.
Names & identifiers
- Preferred name
- Isorhamnetin 3-O-neohesperidoside
- IUPAC
- 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
- English name
- Isorhamnetin 3-O-neohesperoside
- Molecular formula
- C28H32O16
- Molecular weight
- 624.55
Names & synonyms
55033-90-4isorhamnetin 3-O-neohesperidosideDTXSID201298666RefChem:1087813DTXCID601728809Isorhamnetin-3-O-neohespeidosideIsorhamnetin-3-O-nehesperidineIsorhamnetin 3-O-neohesperosideCALENDOFLAVOSIDEIsorhamnetin 3-O-neohesperidinIsorhamnetin 3-O-neohespeidosideMFCD11042252
Show more names
Hesperidin Impurity 8Isorhamnetin-3-O-neohesperosidIsorhamnetin 3-neohesperidoside-RMIsorhamnetin-3-O-neohespeidoside (Standard)Isorhamnetin-3-O-neohespeidoside, 10 mM in DMSOIsorhamnetin 3-O-neohesperidin|||Isorhamnetin 3-O-neohesperoside|||Calendoflavoside
3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-oneIsorhamnetin 3-neohesperidoside3-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-oneIsorhamnetin 3-O-neohesperidineisorhamnetin-3-neohesperidoseIsorhamnetin 3-neohesperosideCHEMBL442566orb1224700
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 255 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 16
- Rotatable bonds
- 7
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 1,040
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Physicochemical properties
- Melting point
- 195 oC · >195oC (dec.)
- Boiling point
- 956.8 · 956.8±65.0 °C(Predicted)
- Density
- 1.74 · 1.74
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
- pka
- 6.17 · 6.17±0.40(Predicted)
- form
- Solid
- color
- Light Yellow to Yellow
- Stability
- Hygroscopic
- Major Application
- food and beverages
- InChIKey
- QHLKSZBFIJJREC-PSKHSWTNNA-N
- SMILES
- O1C(C(C(C(C1C)O)O)O)OC2C(OC(C(C2O)O)CO)OC3=C(Oc5c(c(cc(c5)O)O)C3=O)c4cc(c(cc4)O)OC
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319
- Precautionary statements
- P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Chemistry & industry
Applications
UsesIsorhamnetin 3-O-neohesperidine is a flavonol glycoside extract used as an anti-oxidant.
UsesIsorhamnetin 3-O-neohesperidine is a flavonol glycoside extract used as an anti-oxidant.
Preparation methods
PreparationISORHAMNETIN 3-O-NEOHESPEROSIDE can be generated from typhain (TYP) in the gut microbiota via sequential deglycosylation catalyzed by α-rhamnosidase (Rha) and β-glucosidase (Glu).
Additional notes
DefinitionChEBI: Isorhamnetin-3-O-nehesperidine is a member of flavonoids and a glycoside.
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Compound notes
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