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phloretin
3-(4-hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-one

Supplier Sponsors

Name:3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
CAS Number: 60-82-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:200-488-7
FDA UNII: S5J5OE47MK
Nikkaji Web:J4.808I
Beilstein Number:1887240
MDL:MFCD00002288
XlogP3-AA:2.60 (est)
Molecular Weight:274.27258000
Formula:C15 H14 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:cosmetic and flavor agents
 
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:2022 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-propan-1-one
DG SANTE Food Flavourings:16.109 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
FEMA Number:4390 3-(4-hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-one
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):60-82-2 ; (TRIHYDROXY-PHENYL)-PROPAN-1-ONE
 
Physical Properties:
Appearance:white to pale yellow powder (est)
Assay: 99.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 262.00 to 263.50 °C. @ 760.00 mm Hg
Boiling Point: 534.00 to 535.00 °C. @ 760.00 mm Hg
Flash Point: 556.00 °F. TCC ( 291.11 °C. )
logP (o/w): 2.514 (est)
Shelf Life: 8.00 month(s) or longer if stored properly.
Storage:refrigerate in tightly sealed containers.
Soluble in:
 alcohol, slightly
 water, 123 mg/L @ 16C (exp)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Strength:none
Odor Description:at 100.00 %. odorless
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antioxidants
antiseborrhoeic agents
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Phloretin 98%
Aromiens International
Phloretin Natural
BOC Sciences
For experimental / research use only.
Phloretin
ExtraSynthese
For experimental / research use only.
Phloretin (HPLC) ≥95%
Glentham Life Sciences
Phloretin
Jiangyin Healthway
Phloretin
New functional food ingredients
Jiangyin Healthway
Phloretin
Layn Natural ingredients
Apple Bark Extract Phloretin
Penta International
DIHYDRONARINGENIN
Sigma-Aldrich: Sigma
For experimental / research use only.
Phloretin ≥99%
Skyherb Technologies
Phloretin 98%
TCI AMERICA
For experimental / research use only.
Phloretin >98.0%(HPLC)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
 
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:
oral-rat LD50 [sex: M,F] > 2000 mg/kg
(Vaeth, 2006)

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
cosmetic and flavor agents
Recommendation for phloretin usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 61.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 14000 (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: 23. Update in publication number(s): 26, 30
Click here to view publication 23
 average usual ppmaverage maximum ppm
baked goods: 50.00000150.00000
beverages(nonalcoholic): 50.00000100.00000
beverages(alcoholic): 15.0000050.00000
breakfast cereal: 50.00000100.00000
cheese: 10.0000050.00000
chewing gum: --
condiments / relishes: 10.00000100.00000
confectionery froastings: 20.00000100.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 10.0000050.00000
fruit ices: 20.0000050.00000
gelatins / puddings: 10.00000100.00000
granulated sugar: 20.00000100.00000
gravies: 10.00000100.00000
hard candy: 20.00000100.00000
imitation dairy: 50.00000100.00000
instant coffee / tea: 15.0000050.00000
jams / jellies: 20.0000050.00000
meat products: --
milk products: 10.0000050.00000
nut products: 20.0000050.00000
other grains: 50.00000100.00000
poultry: --
processed fruits: 20.0000050.00000
processed vegetables: 20.0000050.00000
reconstituted vegetables: 50.00000150.00000
seasonings / flavors: 10.00000100.00000
snack foods: 50.00000100.00000
soft candy: 20.00000100.00000
soups: 10.00000100.00000
sugar substitutes: 20.00000100.00000
sweet sauces: 10.00000100.00000
 
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): 40.00000300.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 40.00000300.00000
Edible ices, including sherbet and sorbet (03.0): 30.00000300.00000
Processed fruit (04.1): --
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 20.00000200.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 30.00000300.00000
Bakery wares (07.0): 30.00000300.00000
Meat and meat products, including poultry and game (08.0): 20.00000200.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 30.00000300.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 30.00000300.00000
Foodstuffs intended for particular nutritional uses (13.0): --
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 20.00000300.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 40.00000300.00000
Ready-to-eat savouries (15.0): 30.00000300.00000
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
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :4788
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
Chemidplus:0000060822
 
References:
 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):4788
Pubchem (sid):134970708
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C00774
HMDB (The Human Metabolome Database):HMDB03306
FooDB:FDB015553
Export Tariff Code:2914.50.3000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
FAO:3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-one
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 apple juice - 3-223 mg/l
Search PMC Picture
 apple peel - 80-420 mg/kg
Search PMC Picture
 strawberry wild strawberry fruit - 2-5 mg/kg
Search Trop Picture
 
Synonyms:
 dihydronaringenin
3-(4-hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-one
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl) propan-1-one
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-propan-1-one
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
b-(p-hydroxyphenyl)-2,4,6-trihydroxypropiophenone
beta-(p-hydroxyphenyl)-2,4,6-trihydroxypropiophenone
beta-(para-hydroxyphenyl)-2,4,6-trihydroxypropiophenone
b-(p-hydroxyphenyl)phloropropiophenone
 naringenin dihydrochalcone
1-propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-
 propiophenone, 2',4',6'-trihydroxy-3-(p-hydroxyphenyl)-
2',4',6'-trihydroxy-3-(4-hydroxyphenyl)propiophenone
2',4',6'-trihydroxy-3-(p-hydroxyphenyl) propiophenone
2',4',6'-trihydroxy-3-(p-hydroxyphenyl)propiophenone
2',4',6'-trihydroxy-3-(para-hydroxyphenyl) propiophenone
2',4',6'-trihydroxy-3-(para-hydroxyphenyl)propiophenone
1-(2,4,6-trihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
 

Articles:

PubMed:Identification of enterodiol as a masker for caffeine bitterness by using a pharmacophore model based on structural analogues of homoeriodictyol.
PubMed:Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple.
PubMed:Phloretin promotes osteoclast apoptosis in murine macrophages and inhibits estrogen deficiency-induced osteoporosis in mice.
PubMed:Three-Year Comparative Study of Polyphenol Contents and Antioxidant Capacities in Fruits of Tomato (Lycopersicon esculentum Mill.) Cultivars Grown under Organic and Conventional Conditions.
PubMed:Biochemical and antimicrobial activity of phloretin and its glycosilated derivatives present in apple and kumquat.
PubMed:Essential Structural Requirements and Additive Effects for Flavonoids to Scavenge Methylglyoxal.
PubMed:Immunomodulation of phloretin by impairing dendritic cell activation and function.
PubMed:Hepatoprotective effects and antioxidant, antityrosinase activities of phloretin and phloretin isonicotinyl hydrazone.
PubMed:The estrogenic effects of apigenin, phloretin and myricetin based on uterotrophic assay in immature Wistar albino rats.
PubMed:Phloretin suppresses thrombin-mediated leukocyte-platelet-endothelial interactions.
PubMed:A closed-loop synthetic gene circuit for the treatment of diet-induced obesity in mice.
PubMed:Nonanthocyanin secondary metabolites of black raspberry (Rubus occidentalis L.) fruits: identification by HPLC-DAD, NMR, HPLC-ESI-MS, and ESI-MS/MS analyses.
PubMed:Glucose transport by epithelia prepared from harvested enterocytes.
PubMed:Impacts of selected dietary polyphenols on caramelization in model systems.
PubMed:Post-oral appetite stimulation by sugars and nonmetabolizable sugar analogs.
PubMed:Inhibitory effect of phloretin and biochanin A on IgE-mediated allergic responses in rat basophilic leukemia RBL-2H3 cells.
PubMed:Major active components in grapefruit, orange, and apple juices responsible for OATP2B1-mediated drug interactions.
PubMed:Phloretin and phlorizin promote lipolysis and inhibit inflammation in mouse 3T3-L1 cells and in macrophage-adipocyte co-cultures.
PubMed:Indirect homologous competitive enzyme-linked immunosorbent assay for the detection of a class of glycosylated dihydrochalcones.
PubMed:Flavonoids profiles, antioxidant, acetylcholinesterase inhibition activities of extract from Dryoathyrium boryanum (Willd.) Ching.
PubMed:Transepithelial transport of 6-O-caffeoylsophorose across Caco-2 cell monolayers.
PubMed:Gastrointestinal absorption and metabolism of apple polyphenols ex vivo by the pig intestinal mucosa in the Ussing chamber.
PubMed:Food ingredient extracts of Cyclopia subternata (Honeybush): variation in phenolic composition and antioxidant capacity.
PubMed:Major active components in grapefruit, orange, and apple juices responsible for OATP2B1-mediated drug interactions.
PubMed:Syzygium aqueum leaf extract and its bioactive compounds enhances pre-adipocyte differentiation and 2-NBDG uptake in 3T3-L1 cells.
PubMed:Evaluation of the anti-inflammatory effects of phloretin and phlorizin in lipopolysaccharide-stimulated mouse macrophages.
PubMed:Chemical markers of shiikuwasha juice adulterated with calamondin juice.
PubMed:In vitro attenuation of acrolein-induced toxicity by phloretin, a phenolic compound from apple.
PubMed:Novel antiosteoclastogenic activity of phloretin antagonizing RANKL-induced osteoclast differentiation of murine macrophages.
PubMed:Identification of enterodiol as a masker for caffeine bitterness by using a pharmacophore model based on structural analogues of homoeriodictyol.
PubMed:Evaluation of flavonoids and enterolactone in overnight urine as intake biomarkers of fruits, vegetables and beverages in the Inter99 cohort study using the method of triads.
PubMed:Phloretin inhibits phorbol ester-induced tumor promotion and expression of cyclooxygenase-2 in mouse skin: extracellular signal-regulated kinase and nuclear factor-κB as potential targets.
PubMed:Tiliroside, a glycosidic flavonoid, inhibits carbohydrate digestion and glucose absorption in the gastrointestinal tract.
PubMed:Phloridzin reduces blood glucose levels and improves lipids metabolism in streptozotocin-induced diabetic rats.
PubMed:Impact of phloretin and phloridzin on the formation of Maillard reaction products in aqueous models composed of glucose and L-lysine or its derivatives.
PubMed:Flavonoids in tropical citrus species.
PubMed:Roasting affects phenolic composition and antioxidative activity of hazelnuts (Corylus avellana L.).
PubMed:Colonic availability of polyphenols and D-(-)-quinic acid after apple smoothie consumption.
PubMed:Intestinal transit and systemic metabolism of apple polyphenols.
PubMed:Free fruit at workplace intervention increases total fruit intake: a validation study using 24 h dietary recall and urinary flavonoid excretion.
PubMed:Butein up-regulates the expression of the π class of glutathione S-transferase in rat primary hepatocytes through the ERK/AP-1 pathway.
PubMed:Identification of metabolites in human plasma and urine after consumption of a polyphenol-rich juice drink.
PubMed:No effect of the farming system (organic/conventional) on the bioavailability of apple (Malus domestica Bork., cultivar Golden Delicious) polyphenols in healthy men: a comparative study.
PubMed:Influence of apple polyphenols on inflammatory gene expression.
PubMed:Natural polyphenols as direct trapping agents of lipid peroxidation-derived acrolein and 4-hydroxy-trans-2-nonenal.
PubMed:Phloretin induces apoptosis in H-Ras MCF10A human breast tumor cells through the activation of p53 via JNK and p38 mitogen-activated protein kinase signaling.
PubMed:Phloridzin-induced melanogenesis is mediated by the cAMP signaling pathway.
PubMed:Interspecific variability of antioxidant activities and phenolic composition in Mesembryanthemum genus.
PubMed:Absorption, metabolism, and excretion of cider dihydrochalcones in healthy humans and subjects with an ileostomy.
PubMed:Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple.
PubMed:Fractionation of polyphenol-enriched apple juice extracts to identify constituents with cancer chemopreventive potential.
PubMed:The flavonoids of tomatoes.
PubMed:Induction of apoptosis in HT-29 colon cancer cells by phloretin.
PubMed:Polyphenols are intensively metabolized in the human gastrointestinal tract after apple juice consumption.
PubMed:Comparison of the relative recovery of polyphenolics in two fruit extracts from a model of degradation during digestion and metabolism.
PubMed:Urine flavonoids and plasma carotenoids in the validation of fruit, vegetable and tea intake during pregnancy in the Norwegian Mother and Child Cohort Study (MoBa).
PubMed:Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake.
PubMed:Physiological effects of extraction juices from apple, grape, and red beet pomaces in rats.
PubMed:Cytochrome P450 1A1 expression and activity in Caco-2 cells: modulation by apple juice extract and certain apple polyphenols.
PubMed:Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.
PubMed:Modulation of key elements of the Wnt pathway by apple polyphenols.
PubMed:Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods.
PubMed:The flavonol quercetin-3-glucoside inhibits cyanidin-3-glucoside absorption in vitro.
PubMed:Piceid (resveratrol glucoside) synthesis in stilbene synthase transgenic apple fruit.
PubMed:Use of the 1H nuclear magnetic resonance spectra signals from polyphenols and acids for chemometric characterization of cider apple juices.
PubMed:Phenolic profile of Asturian (Spain) natural cider.
PubMed:Polyphenolic apple juice extracts and their major constituents reduce oxidative damage in human colon cell lines.
PubMed:Colonic availability of apple polyphenols--a study in ileostomy subjects.
PubMed:Interactive effects of polyphenols, tocopherol and ascorbic acid on the Cu2+-mediated oxidative modification of human low density lipoproteins.
PubMed:Degradation of neohesperidin dihydrochalcone by human intestinal bacteria.
PubMed:Role of glucose in modulating Mg2+ homeostasis in liver cells from starved rats.
PubMed:Effects of phenolics in Empire apples on hydrogen peroxide-induced inhibition of gap-junctional intercellular communication.
PubMed:Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context.
PubMed:Major phenolics in apple and their contribution to the total antioxidant capacity.
PubMed:Polyphenolic profiles in eight apple cultivars using high-performance liquid chromatography (HPLC).
PubMed:Response of scab-susceptible (McIntosh) and scab-resistant (Liberty) apple tissues to treatment with yeast extract and Venturia inaequalis.
PubMed:Non-nutritive bioactive food constituents of plants: bioavailability of flavonoids.
PubMed:Dihydrochalcones: evaluation as novel radical scavenging antioxidants.
PubMed:Dietary exposure to xenoestrogens in New Zealand.
PubMed:Detection of phloridzin in strawberries (Fragaria x ananassa Duch.) by HPLC-PDA-MS/MS and NMR spectroscopy.
PubMed:Flavonoids in human urine as biomarkers for intake of fruits and vegetables.
PubMed:Plasma membrane aquaporins in the motor cells of Samanea saman: diurnal and circadian regulation.
PubMed:Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans.
PubMed:Isolation and characterization of stelladerol, a new antioxidant naphthalene glycoside, and other antioxidant glycosides from edible daylily (hemerocallis) flowers.
PubMed:Low temperature metabolism of apple phenolics and quiescence of Phlyctaena vagabunda.
PubMed:Bioavailability of phloretin and phloridzin in rats.
PubMed:Glucose tolerance and peripheral glucose utilization in rainbow trout (Oncorhynchus mykiss), American eel (Anguilla rostrata), and black bullhead catfish (Ameiurus melas).
PubMed:Phloretin glycosides: bioactive compounds in apple fruit, purées, and juices.
PubMed:Inhibition of beta-carotene-15,15'-dioxygenase activity by dietary flavonoids.
PubMed:Phloretin-induced apoptosis in B16 melanoma 4A5 cells and HL60 human leukemia cells.
PubMed:Urea transport processes are induced in rat IMCD subsegments when urine concentrating ability is reduced.
PubMed:Detection of weak estrogenic flavonoids using a recombinant yeast strain and a modified MCF7 cell proliferation assay.
PubMed:Phloretin-induced apoptosis in B16 melanoma 4A5 cells by inhibition of glucose transmembrane transport.
PubMed:[Flavonoid intake of adults in a Bavarian subgroup of the national food consumption survey].
PubMed:Evidence for sodium-dependent active urea secretion in the deepest subsegment of the rat inner medullary collecting duct.
PubMed:Radioprotective effect of antioxidative flavonoids in gamma-ray irradiated mice.
PubMed:Absorption of N4-D-glucopyranosylsulphamethazine by rat everted intestinal sacs.
PubMed:[Detection of fruit juice adulteration in apple and pear juice].
 
Notes:
Phloretin is a dihydrochalcone, a type of natural phenols. It is the phloroglucin ester of paraoxyhydratropic acid. It can be found in apple tree leaves. (Wikipedia)
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