trilobatin
phloretin 4'O-glucoside
Identification
| Name | trilobatin |
| IUPAC | (1R,2S)-3-[(2S,3R,4S,5S)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid |
| CAS Number | 4192-90-9 |
| FDA UNII | 23298I791N |
| Molecular Formula | C25 H24 O13 |
| Molecular Weight | 532.45588000 |
| Nikkaji Number | J1.875.101A |
Regulatory
| JECFA Food Flavoring | 2171 trilobatin |
| DG SANTE Food Flavourings | 16.112 trilobatin |
| FEMA Number | 4674 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 4192-90-9 ; TRILOBATIN |
Physical Properties
| Appearance | pale yellow crystalline powder (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 170.00 to 171.00 °C. @ 760.00 mm Hg |
| Boiling Point | 918.47 °C. @ 760.00 mm Hg (est) |
| Flash Point | 594.00 °F. TCC ( 312.20 °C. ) (est) |
| logP (o/w) | -1.653 (est) |
| Soluble in | water, 5.885e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor enhancers, bitter taste blockers |
| Recommendation for trilobatin usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 1200.00 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 66000 (μg/person/day) |
| Threshold of Concern | 90 (μg/person/day) |
| Structure Class | III |
| baked goods | - |
| beverages(nonalcoholic) | 100.00000 |
| beverages(alcoholic) | - |
| breakfast cereal | 100.00000 |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | 250.00000 |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
| Dairy products, excluding products of category 02.0 (01.0) | 250.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | - |
| Edible ices, including sherbet and sorbet (03.0) | - |
| Processed fruit (04.1) | - |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | - |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 100.00000 |
| Bakery wares (07.0) | - |
| Meat and meat products, including poultry and game (08.0) | - |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | - |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | - |
| Foodstuffs intended for particular nutritional uses (13.0) | - |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 100.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | - |
| Ready-to-eat savouries (15.0) | - |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | - |
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Potential Uses
Natural Occurrence
Synonyms
(1R,2S)-3-[(2S,3R,4S,5S)-2-(
carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
1-[4-(beta-D-
glucopyranosyloxy)-2,6-dihydroxyphenyl-3-(4-hydroxyphenyl)]-1-propanone
1-[4-(beta-D-
glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
4’-O-beta-D-
glucoside of phloretin
phloretin 4'-glucoside
phloretin 4'O-glucoside
prunin dihydrochalcone
trilobatin D
trilobatin natural
Google Patents:
Bitter Alkaloid Containing Consumables Comprising Bitter Blockers
WIPO Patents:
BITTER ALKALOID CONTAINING CONSUMABLES COMPRISING BITTER BLOCKERS
PubMed:
Trilobatin attenuates the LPS-mediated inflammatory response by suppressing the NF-κB signaling pathway.
Leffingwell & Associates:
Flavor Properties of FEMA GRAS List 25 flavor chemicals
PubMed:
Histolocalization and physico-chemical characterization of dihydrochalcones: Insight into the role of apple major flavonoids.
PubMed:
Identification of metabolites in human plasma and urine after consumption of a polyphenol-rich juice drink.
PubMed:
Dihydrochalcones: Implication in resistance to oxidative stress and bioactivities against advanced glycation end-products and vasoconstriction.
PubMed:
Expression of a Dianthus flavonoid glucosyltransferase in Saccharomyces cerevisiae for whole-cell biocatalysis.
PubMed:
Polyphenols are intensively metabolized in the human gastrointestinal tract after apple juice consumption.
PubMed:
Interaction of flavonoids and intestinal facilitated glucose transporters.
PubMed:
Antioxidant activities of three dihydrochalcone glucosides from leaves of Lithocarpus pachyphyllus.
PubMed:
A new sweet dihydrochalcone-glucoside from leaves of Lithocarpus pachyphyllus (Kurz) Rehd. (Fagaceae).
PubMed:
Lignan derivatives from the liverwort Bazzania trilobata.
PubMed:
Crystal structure of phlorizin and the iodothyronine deiodinase inhibitory activity of phloretin analogues.