<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:22 UTC</creation_date>
  <update_date>2025-11-18 22:37:19 UTC</update_date>
  <accession>FDB002416</accession>
  <name>Neohesperidin dihydrochalcone</name>
  <description>Intensely 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.</description>
  <synonyms>
    <synonym>E959</synonym>
    <synonym>FEMA 3811</synonym>
    <synonym>Neohesperidin DC</synonym>
    <synonym>Neohesperidin DHC</synonym>
    <synonym>Neohesperidine dihydrochalcone</synonym>
    <synonym>NHDC</synonym>
    <synonym>NHDHC</synonym>
  </synonyms>
  <chemical_formula>C28H36O15</chemical_formula>
  <average_molecular_weight>612.5764</average_molecular_weight>
  <monisotopic_moleculate_weight>612.205420482</monisotopic_moleculate_weight>
  <iupac_name>1-(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</iupac_name>
  <traditional_iupac>1-(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_iupac>
  <cas_registry_number>20702-77-6</cas_registry_number>
  <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</smiles>
  <inchi>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>
  <inchikey>ITVGXXMINPYUHD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <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).</description>
    <direct_parent>Flavones</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Flavonoids</class>
    <sub_class>Flavones</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>4'-hydroxyflavonoids</alternative_parent>
      <alternative_parent>5-hydroxyflavonoids</alternative_parent>
      <alternative_parent>7-hydroxyflavonoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Chromones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyranones and derivatives</alternative_parent>
      <alternative_parent>Resorcinols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>4'-hydroxyflavonoid</substituent>
      <substituent>5-hydroxyflavonoid</substituent>
      <substituent>7-hydroxyflavonoid</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromone</substituent>
      <substituent>Flavone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyflavonoid</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyranone</substituent>
      <substituent>Resorcinol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Flavones and Flavonols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.04e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.56</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-(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</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>612.5764</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>612.205420482</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>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</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C28H36O15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>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</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>ITVGXXMINPYUHD-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>245.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>143.18</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>61.16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>10</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>41982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527995</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527996</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527997</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527998</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527999</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>528000</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>528001</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>528002</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>528003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>528004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>528005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313226</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313227</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358669</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358670</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358671</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440362</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440363</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440364</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2229752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2232033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2232181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2234576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2236270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2237097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2238364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2239232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2240348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2241336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2243394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2251620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2777291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2777292</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2777293</spectrum_id>
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  </spectra>
  <hmdb_id>HMDB30542</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce33044438&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Sweet orange</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus sinensis</name_scientific>
      <ncbi_taxonomy_id>2711</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
    <flavor>
      <name>bland</name>
    </flavor>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Sweetener</name>
      <id>1341</id>
      <definition>Substance that sweeten food, beverages, medications, etc.</definition>
    </health_effect>
  </health_effects>
</compound>
