trilobatin

phloretin 4'O-glucoside

CAS: 4192-90-9 C25 H24 O13 MW: 532.45588000

Identification

Nametrilobatin
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 Number4192-90-9
FDA UNII23298I791N
Molecular FormulaC25 H24 O13
Molecular Weight532.45588000
Nikkaji NumberJ1.875.101A

Regulatory

JECFA Food Flavoring2171 trilobatin
DG SANTE Food Flavourings16.112 trilobatin
FEMA Number4674
FDANo 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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor enhancers, bitter taste blockers
Recommendation for trilobatin usage levels up tonot 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 Concern90 (μg/person/day)
Structure ClassIII
baked goods-
beverages(nonalcoholic)100.00000
beverages(alcoholic)-
breakfast cereal100.00000
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 products250.00000
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

None Found

Natural Occurrence

bazzania trilobata lithocarpus litseifolius lithocarpus pachyphyllus malus trilobata - up to 10000 mg/kg vitis piasezkii maxim. vitis saccharifera makino

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.