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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:31 UTC
Update Date2017-12-07 03:05:43 UTC
HMDB IDHMDB0030542
Secondary Accession Numbers
  • HMDB30542
Metabolite Identification
Common NameNeohesperidin dihydrochalcone
DescriptionNeohesperidin dihydrochalcone is found in sweet orange. Intensely sweet, 612 times more sweet than sucrose. Acceptable daily intake: 5 mg/kg (1987). Neohesperidin dihydrochalcone is a permitted in EU at low concs. (=10 ppm) for certain applications, e.g. low-alcohol beer. Generally recognised as safe (GRAS) in the USA. Practical use limited by slow development of taste sensation and peculiar aftertaste Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus. The European Union approved NHDC's use as a sweetener in 1994. It has not been approved as a sweetener in the United States. It is sometimes said that NHDC is considered a Generally Recognized as Safe flavour enhancer by the Flavour and Extract Manufacturers' Association, which is a trade group with no legal standing. NHDC has never appeared on the FDA's GRAS listing
Structure
Thumb
Synonyms
ValueSource
e959HMDB
FEMA 3811HMDB
Neohesperidin DCHMDB
Neohesperidin DHCHMDB
Neohesperidine dihydrochalconeHMDB
NHDCHMDB
NHDHCHMDB
Chemical FormulaC28H36O15
Average Molecular Weight612.5764
Monoisotopic Molecular Weight612.205420482
IUPAC Name1-(4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
Traditional Name1-(4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
CAS Registry Number20702-77-6
SMILES
COC1=C(O)C=C(CCC(=O)C2=C(O)C=C(OC3OC(CO)C(O)C(O)C3OC3OC(C)C(O)C(O)C3O)C=C2O)C=C1
InChI Identifier
InChI=1S/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3
InChI KeyITVGXXMINPYUHD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • 2'-hydroxy-dihydrochalcone
  • Phenolic glycoside
  • Linear 1,3-diarylpropanoid
  • Cinnamylphenol
  • Alkyl-phenylketone
  • Butyrophenone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • Phenylketone
  • Anisole
  • Benzoyl
  • Phenoxy compound
  • Phenol ether
  • Resorcinol
  • Methoxybenzene
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Polyol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.04 g/LALOGPS
logP0.05ALOGPS
logP0.75ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area245.29 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity143.18 m³·mol⁻¹ChemAxon
Polarizability61.16 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06xt-8310290000-70c126cb27d33cd6a0f8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-8321219000-3351a2ec5ab3466ee955View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0000009000-affa0e0ef92b5a22a553View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0001009000-828aa8353246f5f4043dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009103000-97bc3acb4370bf9313c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mk-0347932000-1d07f46ccaee0e62e4cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0759400000-412eb003c1a6c468a1caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbj-1934100000-513144f3b70ba577b270View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ika-3529756000-348c3d61ba60c329ed2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2a-1935410000-5647dd01a5ce5d1737a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9857100000-9eaf26dd3ed05b6365fcView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002416
KNApSAcK IDNot Available
Chemspider ID4298
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeohesperidin dihydrochalcone
METLIN IDNot Available
PubChem Compound4453
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .