1-(4-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one

• ChemBase ID: 72963
• Molecular Formular: C28H36O15
• Molecular Mass: 612.57644
• Monoisotopic Mass: 612.20542045
• SMILES: c1c(cc(c(c1O)C(=O)CCc1cc(c(cc1)OC)O)O)O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O[C@H]1[C@H](O)[C@@H]([C@H]([C@@H](O1)C)O)O)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c(c(c2)O)C(=O)CCc2ccc(c(c2)O)OC)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
• 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/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChIKey: ITVGXXMINPYUHD-CUVHLRMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-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 Traditional name: neohesperidin dihydrochalcone
• Synonyms: Nhdc; Neohesperidin dc; Neohesperidin dhc; Neohesperidin dihydrochalcone; 1-(4-((2-O-[6-Deoxy-α-L-mannopyranosyl]-β-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-methoxyphenyl]-1-propanone; Neohesperidin dihydrochalcone; 1-[4-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-1-propanone; Neohesperidine Dihydrochalcone; 新橙皮苷二氢查尔酮

Database IDs

• CAS Number: 20702-77-6
• EC Number: 243-978-6
• MDL Number: MFCD00017711
• PubChem SID: 24901889; 162037883; 24897690
• PubChem CID: 30231
• FEMA ID: 3811
• Wikipedia Title: Neohesperidin_dihydrochalcone
• Flavis Number: 16.061

CALCULATED PROPERTIES

• Acid pKa: 9.56446
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): 0.74583834
• LogD (pH = 7.4): 0.74292827
• Log P: 0.7458755
• Molar Refractivity: 143.1845 cm^3
• Polarizability: 57.317883 Å^3
• Polar Surface Area: 245.29 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >150°C (dec.); 156-158 °C(lit.)
• Sweetness: 1500 × sucrose
• Organoleptic: orange; sweet

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥85%; ≥95% (HPLC)
• Grade: Halal; Kosher
• Salt Data: Free Base
• Biological Source: from citrus fruit
• Empirical Formula (Hill Notation): C28H36O15

DETAILS

Selleck Chemicals - S2331

Research Area: Neurological Disease
Biological Activity:
Neohesperidin dihydrochalcone(Nhdc), sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus. The product is well known for having a strong synergistic effect when used in conjunction with other artificial sweeteners. As a flavour enhancer, NHDC is used in a wide range of products and is indicated by the E number E 959. It is noted particularly for enhancing sensory effects. [1]

Sigma Aldrich - N8757

Biochem/physiol Actions
Flavonoid sweetening agent with potent antioxidant activity.1

Sigma Aldrich - W381101

Packaging
1 sample in glass bottle
25, 100 g in poly bottle

Toronto Research Chemicals - N389950

Preparation from Naringen, a flavanone glycoside occurring naturally in grapefruit. It is used as sweetening agent, especially in chewing gum and dentifrices.

REFERENCES

• http://en.wikipedia.org/wiki/Neohesperidin_dihydrochalcone
• Inglett, et al.: J. Food Sci., 34, 101 (1969)
• Fisher, J.F., J. Agric. Food Chem., 25, 682 (1969)
• Pratter, P.J., Perfum. Flavor., 5, 12 (1969)
• Lina, B.A.R., et al.: Food Chem. Toxicol., 28, 507 (1969)