EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

trilobatin
phloretin 4'O-glucoside

Supplier Sponsors

Name:(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: 4192-90-9Picture of molecule3D/inchi
FDA UNII: 23298I791N
Nikkaji Web:J1.875.101A
XlogP3-AA:-0.10 (est)
Molecular Weight:532.45588000
Formula:C25 H24 O13
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:flavor enhancers, bitter taste blockers
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:2171 trilobatin
DG SANTE Food Flavourings:16.112 trilobatin
FEMA Number:4674 trilobatin
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)
 alcohol
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Trilobatin 98%
Aromiens International
Trilobatin Natural
BOC Sciences
For experimental / research use only.
p-Phlorizin
Carbosynth
For experimental / research use only.
Trilobatin
Coompo
For experimental / research use only.
Trilobatin from Plants ≥96%
Odor: characteristic
Use: The IC50 (50% inhibitory concentration) values for trilobatin of lipid peroxidation in rat liver homogenate was 88 µm. Trilobatin increased superoxide dismutase (SOD) activity with EC50 (50% effective concentration) values of 128 µm, and glutathione peroxidase (GSH-Px) activity with EC50 values of 129 µm, and showed only weak DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity. The inhibitory activities of trilobatin against a-glucosidase and a-amylase were evaluated, and the inhibition mechanism was analysed with Lineweaver–Burk plots. Also the antioxidant activity evaluation of trilobatin was conducted by DPPH radical scavenging assay. Comparing with acarbose, trilobatin showed a strong inhibitory activity against a-glucosidase and a moderate inhibitory activity against a-amylase. The Lineweaver–Burk plots analysis elucidated that trilobatin inhibited the enzyme non-competitively. DPPH scavenging activity of trilobatin (IC50 = 0.57 mg/ml) was higher than rutin (IC50 = 0.72 mg/ml), which indicated that trilobatin had a moderate antioxidant potential. These results suggest that trilobatin is a potential effective a-glucosidase inhibitor for management of postprandial hyperglycemia with less side effect, and provide strong rationale for further animal and clinical studies.
ExtraSynthese
For experimental / research use only.
Trilobatin (HPLC) ≥99%
Jiangyin Healthway
Trilobatin
New functional food ingredients
Jiangyin Healthway
Trilobatin
Parchem
trilobatin
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 25
Click here to view publication 25
 average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): 100.0000010.00000
beverages(alcoholic): --
breakfast cereal: 100.00000100.00000
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: 250.00000750.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 250.00000750.00000
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): 100.00000100.00000
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): 100.00000100.00000
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): --
 
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 32 (FGE.32): Flavonoids (Flavanones and dihydrochalcones) from chemical groups 25 and 30
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :637238
National Institute of Allergy and Infectious Diseases:Data
(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
Chemidplus:0004192909
 
References:
 (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
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):637238
Pubchem (sid):53431190
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
HMDB (The Human Metabolome Database):HMDB37505
FooDB:FDB016580
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bazzania trilobata
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 lithocarpus litseifolius
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 lithocarpus pachyphyllus
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 malus trilobata - up to 10000 mg/kg
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 vitis piasezkii maxim.
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 vitis saccharifera makino
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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
 

Articles:

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-ÎşB 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.
 
Notes:
Isol. from apple leaves
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