(TRIHYDROXY-PHENYL)-PROPAN-1-ONE (CED0042225)

Record Information
Version1.0
Creation Date2016-05-19 02:29:37 UTC
Update Date2026-05-14 18:47:19 UTC
Accession NumberCHEM007729
Identification
Common Name(TRIHYDROXY-PHENYL)-PROPAN-1-ONE
ClassSmall Molecule
Description
(TRIHYDROXY-PHENYL)-PROPAN-1-ONE belongs to the chalcones and dihydrochalcones, a subclass of linear 1,3-diarylpropanoids within the organic compounds. This compound has the chemical formula C15H14O5 and an average molecular weight of 274.27 g/mol. Industrially, it is utilized as an antioxidant, a pharmaceutical agent, and as a flavouring and nutrient. The compound is found in or released from ten recorded sources. These include food, food processing and cookware, specifically within fermentation processes for beer, food preservation, and the preparation of vinegar, wine, or sparkling wine. It is also present in household cleaning and consumer products, such as cigar cigarettes, soap detergents, and perfumes within detergents and soaps. Additionally, it is associated with electrical and electronic equipment, including electrodes and electrically stimulated smoking devices, as well as indoor air, dust and atmospheric transport. The recorded route of exposure for this substance is inhalation. Regarding its biological activity, there are two recorded protein targets for (TRIHYDROXY-PHENYL)-PROPAN-1-ONE: the solute carrier family 23 member 1 (SLC23A1) and the HTH-type transcriptional regulator TtgR (ttgR), which it inhibits. In the context of materials, the compound is unspecified in polycarbonate plastics.
Contaminant Type
  • Phenolic Antioxidant
Chemical Structure
Synonyms
ValueSource
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanoneChEBI
2,6-Dihydroxy-4-methoxyacetophenoneHMDB
4-O-MethylphloracetophenoneHMDB
DihydronaringeninHMDB
PhloretolHMDB
Chemical FormulaC15H14O5
Average Molecular Mass274.269 g/mol
Monoisotopic Mass274.084 g/mol
CAS Registry Number60-82-2
IUPAC Name3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
Traditional Namephloretin
SMILESOC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1
InChI IdentifierInChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
InChI KeyVGEREEWJJVICBM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxy-dihydrochalcones
Alternative Parents
Substituents
  • 2'-hydroxy-dihydrochalcone
  • Cinnamylphenol
  • Alkyl-phenylketone
  • Acylphloroglucinol derivative
  • Butyrophenone
  • Benzenetriol
  • Phloroglucinol derivative
  • Phenylketone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.23ALOGPS
logP3.9ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.96ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.71 m³·mol⁻¹ChemAxon
Polarizability27.75 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-002f-0915000000-2cd118505cf4ff16b664Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-002f-0915000000-2cd118505cf4ff16b664Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udi-2920000000-ce9a5fce0e77c981b6d3Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00r2-2207490000-670b5b16c28fb6b692e3Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-1900000000-b990d3eca878be81222bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-2900000000-4eb9bf83b7d70a97bd0bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0w2c-4900000000-77d3779ddd5455f0b9a3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-a2a168a2f04c479df8edNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-0090050000-15d417468db5c396463eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-bc6e2e1009d1b50ad9f7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00xr-0690000000-e5774d71d08a1df83336Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-d051b74295a78047c5f0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-0900000000-6e6539df4cbbef8d26b3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-0940000000-e06c676ae64bfbb5107bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-949e95a0767d512e3d04Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0910000000-bb2134d05e29fff0bc78Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0910000000-eb3ed13a8222a6f19622Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0910000000-667b033138f7ace9d55fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fmi-0023970000-393be1dcce343cb4741eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0umi-0023970000-3a5237456ae522f69560Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0umi-0024970000-1b94154d82b12915f577Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-0940000000-4efa4b943568aeb36bfeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-f6a73eb3753eaa9c13acNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-0c999f95c930697ca836Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-b071b34e8decf08d20cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-ed2c23e84df7f42a0a67Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-c8896aeaf8559ac26f93Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-d57cecd4ec328ffa5040Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-52e9b7bfdbff1b9771bdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-0920000000-9caa394f42bff9a3a176Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-0930000000-707d689e0109c4da44adNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05mk-0900000000-1ec430b21e18e54b2f28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-382cf9f54c36e8bc5f17Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00xr-0890000000-4be9eff64b559206bbb1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-0910000000-b1fa93a4eb0388450849Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-5cf6eb41e5f7f3cf9afbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-13aa878371a018748296Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00xr-0690000000-660bfcd514007006f3a1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-d57cecd4ec328ffa5040Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-52e9b7bfdbff1b9771bdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-0940000000-4efa4b943568aeb36bfeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-0900000000-b65859093d166694ddadNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-0af67d07416c2b9faf6aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-52cf8f591f7fe63a366eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9400000000-1a3fbea29c823ac55118Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-050bed0651a8b9c7e93dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-8f9870b6528d80605eefNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-fa91edd073ba1dcd6377Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0910000000-6054983123ad2fb284c2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-b071b34e8decf08d20cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-055ae102fbdbb687b918Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-0940000000-f5922cc5e5dc886aabccNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-f6a73eb3753eaa9c13acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0290000000-826fa92be2be280f2e5eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-0930000000-6abeede53ef1753e2613Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2900000000-a2ba5d714e72373837bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0290000000-8a18e7ae5b70f7a0683fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00b9-0930000000-66ecbda03ca96ea053b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-3910000000-831048d96d049d47cd92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0290000000-826fa92be2be280f2e5eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-0930000000-6abeede53ef1753e2613Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2900000000-a2ba5d714e72373837bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0290000000-8a18e7ae5b70f7a0683fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00b9-0930000000-66ecbda03ca96ea053b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-3910000000-831048d96d049d47cd92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004j-0960000000-d72fb5c1fc0c74102c03Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zmi-0900000000-dab0aa5eb93692520651Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ufr-4910000000-b505e802ffebb610dc59Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0290000000-c27cb44ec86fceb340d4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0g6r-0930000000-c99f542cbb81ba2e9cf1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00r6-9600000000-21235cf6af3a97f9d90fNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2556.0Log mg/kg[1400:4500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
491Industrial manufacturing & chemical processingNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)8.56341
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)41.805
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)8.64126
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)1.32344
Click to view 3D structurePhosphatidylcholine:ceramide cholinephosphotransferase 1Q86VZ5HumansPredicted (SEA)0.233548
Click to view 3D structurePhosphatidylcholine:ceramide cholinephosphotransferase 2Q8NHU3HumansPredicted (SEA)0.311397
Monocarboxylate transporter 1 structureClick to view 3D structureMonocarboxylate transporter 1P53985HumansPredicted (SEA)1.71268
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 3Q64518Mus musculusPredicted (SEA)4.82665
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)77.46
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)16.6597
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)19.2288
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)152.74
Tyrosinase structureClick to view 3D structureTyrosinaseP14679HumansPredicted (SEA)3.65891
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)155.698
Click to view 3D structureTrypanothione reductaseP39040Crithidia fasciculataPredicted (SEA)2.95827
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)160.681
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)97.8565
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)55.74
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)61.0338
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)74.5796
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)37.1341
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)180.454
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)202.486
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)276.598
Click to view 3D structurePolyphenol oxidase 1Q00024Agaricus bisporusPredicted (SEA)0.622794
Concentrations
Not Available
External Links
DrugBank IDDB07810
HMDB IDHMDB0003306
FooDB IDFDB015553
Phenol Explorer ID108
KNApSAcK IDC00007936
BiGG IDNot Available
BioCyc IDPHLORETIN
METLIN ID3405
PDB IDNot Available
Wikipedia LinkPhloretin
Chemspider ID4624
ChEBI ID17276
PubChem Compound ID4788
Kegg Compound IDC00774
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sharif NA, Crider JY, Davis TL: AL-3138 antagonizes FP prostanoid receptor-mediated inositol phosphates generation: comparison with some purported FP antagonists. J Pharm Pharmacol. 2000 Dec;52(12):1529-39.
2. Fan HT, Morishima S, Kida H, Okada Y: Phloretin differentially inhibits volume-sensitive and cyclic AMP-activated, but not Ca-activated, Cl(-) channels. Br J Pharmacol. 2001 Aug;133(7):1096-106.
3. Stangl V, Lorenz M, Ludwig A, Grimbo N, Guether C, Sanad W, Ziemer S, Martus P, Baumann G, Stangl K: The flavonoid phloretin suppresses stimulated expression of endothelial adhesion molecules and reduces activation of human platelets. J Nutr. 2005 Feb;135(2):172-8.
4. Rasmussen SE, Breinholt VM: Non-nutritive bioactive food constituents of plants: bioavailability of flavonoids. Int J Vitam Nutr Res. 2003 Mar;73(2):101-11.
5. Nielsen SE, Freese R, Kleemola P, Mutanen M: Flavonoids in human urine as biomarkers for intake of fruits and vegetables. Cancer Epidemiol Biomarkers Prev. 2002 May;11(5):459-66.
6. DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5.
7. Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9.
8. Zerbini G, Podesta F, Meregalli G, Deferrari G, Pontremoli R: Fibroblast Na+-Li+ countertransport rate is elevated in essential hypertension. J Hypertens. 2001 Jul;19(7):1263-9.
9. Park SY, Kim EJ, Shin HK, Kwon DY, Kim MS, Surh YJ, Park JH: Induction of apoptosis in HT-29 colon cancer cells by phloretin. J Med Food. 2007 Dec;10(4):581-6.
10. Tombola F, Morbiato L, Del Giudice G, Rappuoli R, Zoratti M, Papini E: The Helicobacter pylori VacA toxin is a urea permease that promotes urea diffusion across epithelia. J Clin Invest. 2001 Sep;108(6):929-37.
11. Pajor AM, Randolph KM, Kerner SA, Smith CD: Inhibitor binding in the human renal low- and high-affinity Na+/glucose cotransporters. J Pharmacol Exp Ther. 2008 Mar;324(3):985-91. Epub 2007 Dec 6.
12. Rezk BM, Haenen GR, van der Vijgh WJ, Bast A: The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem Biophys Res Commun. 2002 Jul 5;295(1):9-13.
13. Pandey RP, Li TF, Kim EH, Yamaguchi T, Park YI, Kim JS, Sohng JK: Enzymatic synthesis of novel phloretin glucosides. Appl Environ Microbiol. 2013 Jun;79(11):3516-21. doi: 10.1128/AEM.00409-13. Epub 2013 Mar 29.
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18767070
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23907072
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24487097
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7126563