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W381101

Sigma-Aldrich

Neohesperidin dihydrochalcone

≥96%, FG

Synonym(s):

1-(4-((2-O-[6-Deoxy-α-L-mannopyranosyl]-β-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-methoxyphenyl]-1-propanone, NHDC

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About This Item

Empirical Formula (Hill Notation):
C28H36O15
CAS Number:
20702-77-6
Molecular Weight:
612.58
FEMA Number:
3811
EC Number:
243-978-6
MDL number:
MFCD00017711
UNSPSC Code:
12164502
PubChem Substance ID:
24901889
Flavis number:
16.061
E Number:
E 959
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 872/2012

Assay

≥96%

mp

156-158 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

odorless

storage temp.

2-8°C

SMILES string

COc1ccc(CCC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)cc2O)cc1O

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

InChI key

ITVGXXMINPYUHD-CUVHLRMHSA-N

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General description

Neohesperidin dihydrochalcone is mainly used as a sweetener and flavoring agent. It can be prepared by the hydrogenation of neohesperidin, a bitter flavonone found in citrus fruits.

Application

  • Neohesperidin dihydrochalcone down-regulates MyD88-dependent and -independent signaling by inhibiting endotoxin-induced trafficking of TLR4 to lipid rafts.: This study explores the molecular mechanisms behind the immunomodulatory effects of Neohesperidin dihydrochalcone, revealing its potential to mitigate endotoxin-induced inflammatory responses (Xia et al., 2015).

    • Pictograms

    Exclamation mark
    GHS07

    Signal Word

    Warning

    Hazard Statements

    H302

    Precautionary Statements

    P264 - P270 - P301 + P312 - P501

    Hazard Classifications

    Acute Tox. 4 Oral

    Storage Class Code

    11 - Combustible Solids

    WGK

    WGK 3

    Flash Point(F)

    Not applicable

    Flash Point(C)

    Not applicable

    Personal Protective Equipment

    dust mask type N95 (US), Eyeshields, Gloves

    Certificates of Analysis (COA)

    Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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    Neohesperidin dihydrochalcone; an updated review on a naturally derived sweetener and flavor potentiator.
    Pratter PJ
    Perfumer & Flavorist (1980)
    Alternative Sweeteners, 87-104 null
    H Montijano et al.
    Journal of chromatography. A, 758(1), 163-166 (1997-01-10)
    An analytical method to detect and quantitate neohesperidine dihydrochalcone in foodstuffs has been developed and validated in soft-drink applications. The method was shown to be sufficiently precise, accurate, selective and rugged in quantitating neohesperidine DC both at flavouring (1-5 mg/kg)
    A Ly et al.
    Chemical senses, 26(1), 41-47 (2000-12-22)
    The genetically determined ability to taste 6-n-propylthiouracil (PROP) has been linked with lowered acceptance of some bitter foods. Fifty-four women, aged 18-30 years, tasted and rated PROP-impregnated filter paper and seven solutions of PROP. Summed bitterness intensity ratings for PROP
    Annett Braune et al.
    Journal of agricultural and food chemistry, 53(5), 1782-1790 (2005-03-03)
    The degradation of neohesperidin dihydrochalcone by human intestinal microbiota was studied in vitro. Human fecal slurries converted neohesperidin dihydrochalcone anoxically to 3-(3-hydroxy-4-methoxyphenyl)propionic acid or 3-(3,4-dihydroxyphenyl)propionic acid. Two transient intermediates were identified as hesperetin dihydrochalcone 4'-beta-d-glucoside and hesperetin dihydrochalcone. These metabolites
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