Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:22 UTC |
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Update date | 2020-02-24 19:10:30 UTC |
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Primary ID | FDB002416 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Neohesperidin dihydrochalcone |
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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. |
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CAS Number | 20702-77-6 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C28H36O15 |
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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 |
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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 |
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InChI Key | ITVGXXMINPYUHD-UHFFFAOYSA-N |
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Isomeric 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 |
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Average Molecular Weight | 612.5764 |
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Monoisotopic Molecular Weight | 612.205420482 |
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Classification |
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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). |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavones |
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Direct Parent | Flavones |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Neohesperidin dihydrochalcone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-06xt-8310290000-70c126cb27d33cd6a0f8 | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01b9-8321219000-3351a2ec5ab3466ee955 | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Neohesperidin dihydrochalcone, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-03di-0000009000-affa0e0ef92b5a22a553 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-03di-0001009000-828aa8353246f5f4043d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-0udi-0009103000-97bc3acb4370bf9313c9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0gdi-0930000000-503a25939278999a7d88 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0gdi-0930000000-2f58d84bd781c55c7089 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0udi-0109000000-2f5e31c9304c57a0d048 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0926612000-6c559ef36161bac02608 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0udi-0119000000-6ebccd6901f09ecbc6b5 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-03di-0000009000-842a371da79090657c35 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-03di-0000009000-1c0c2ce0aeab9012ac0d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0gdi-0930000000-e234c74c6290f63c36fa | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-0udi-0109000000-c286178708e6b654ef6e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-03di-0104009000-025c37838d966e13ad90 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-004i-0926612000-cd160b87f3e27f6a3b9a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Negative | splash10-03di-0104009000-b0b615464d79fe538789 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-03di-0104009000-5763211fc3891fd3ff94 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05mk-0347932000-1d07f46ccaee0e62e4cb | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-0759400000-412eb003c1a6c468a1ca | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pbj-1934100000-513144f3b70ba577b270 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ika-3529756000-348c3d61ba60c329ed2b | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0w2a-1935410000-5647dd01a5ce5d1737a3 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-9857100000-9eaf26dd3ed05b6365fc | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0101139000-245a7c0ba502562d6690 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1951221000-9414417759024670db34 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0553-2910012000-67093ef1fd2eb94ba1c8 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4298 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 4453 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB30542 |
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CRC / DFC (Dictionary of Food Compounds) ID | CLR49-U:CLR49-U |
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EAFUS ID | 2646 |
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Dr. Duke ID | NEOHESPERIDIN-DIHYDROCHALCONE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1003941 |
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SuperScent ID | Not Available |
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Wikipedia ID | Neohesperidin_dihydrochalcone |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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