Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2020-02-24 19:10:30 UTC
Primary IDFDB002416
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNeohesperidin dihydrochalcone
DescriptionIntensely sweet, 612 times more sweet than sucrose. ADI 5 mg/kg (1987). 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. Neohesperidin dihydrochalcone is found in sweet orange.
CAS Number20702-77-6
Structure
Thumb
Synonyms
SynonymSource
e959HMDB
FEMA 3811HMDB
Neohesperidin DCHMDB
Neohesperidin DHCHMDB
Neohesperidine dihydrochalconeHMDB, MeSH
NHDCHMDB
NHDHCHMDB
Neohesperidin dihydrochalconeMeSH
Neohesperidine DCMeSH
E959db_source
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H36O15
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
InChI IdentifierInChI=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
Isomeric SMILESCOC1=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
Average Molecular Weight612.5764
Monoisotopic Molecular Weight612.205420482
Classification
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.90%; H 5.92%; O 39.18%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNeohesperidin dihydrochalcone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06xt-8310290000-70c126cb27d33cd6a0f8Spectrum
Predicted GC-MSNeohesperidin dihydrochalcone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-8321219000-3351a2ec5ab3466ee955Spectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeohesperidin dihydrochalcone, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0000009000-affa0e0ef92b5a22a5532017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0001009000-828aa8353246f5f4043d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009103000-97bc3acb4370bf9313c92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gdi-0930000000-503a25939278999a7d882021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gdi-0930000000-2f58d84bd781c55c70892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0109000000-2f5e31c9304c57a0d0482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0926612000-6c559ef36161bac026082021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0119000000-6ebccd6901f09ecbc6b52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0000009000-842a371da79090657c352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0000009000-1c0c2ce0aeab9012ac0d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gdi-0930000000-e234c74c6290f63c36fa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0109000000-c286178708e6b654ef6e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0104009000-025c37838d966e13ad902021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0926612000-cd160b87f3e27f6a3b9a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-03di-0104009000-b0b615464d79fe5387892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0104009000-5763211fc3891fd3ff942021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mk-0347932000-1d07f46ccaee0e62e4cb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0759400000-412eb003c1a6c468a1ca2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbj-1934100000-513144f3b70ba577b2702017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ika-3529756000-348c3d61ba60c329ed2b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2a-1935410000-5647dd01a5ce5d1737a32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9857100000-9eaf26dd3ed05b6365fc2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0101139000-245a7c0ba502562d66902021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1951221000-9414417759024670db342021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0553-2910012000-67093ef1fd2eb94ba1c82021-09-24View Spectrum
NMRNot Available
ChemSpider ID4298
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID4453
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30542
CRC / DFC (Dictionary of Food Compounds) IDCLR49-U:CLR49-U
EAFUS ID2646
Dr. Duke IDNEOHESPERIDIN-DIHYDROCHALCONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1003941
SuperScent IDNot Available
Wikipedia IDNeohesperidin_dihydrochalcone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
sweetener50505 Substance that sweeten food, beverages, medications, etc.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bland
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).