Phlorizin
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Hodoodo CAT#: H329650

CAS#: 60-81-1

Description: Phlorizin, also referred to as phloridzin, is a glucoside of phloretin, a dihydrochalcone, a family of bicyclic flavonoids, which in turn is a subgroup in the diverse phenylpropanoid synthesis pathway in plants. Phlorizin is a competitive inhibitor of SGLT1 and SGLT2 because it competes with D-glucose for binding to the carrier; this reduces renal glucose transport, lowering the amount of glucose in the blood. Phlorizin was studied as a potential pharmaceutical treatment for type 2 diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as canagliflozin and dapagliflozin.


Chemical Structure

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Phlorizin
CAS# 60-81-1

Theoretical Analysis

Hodoodo Cat#: H329650
Name: Phlorizin
CAS#: 60-81-1
Chemical Formula: C21H24O10
Exact Mass: 436.14
Molecular Weight: 436.413
Elemental Analysis: C, 57.80; H, 5.54; O, 36.66

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
5g USD 550 2 Weeks
10g USD 850 2 Weeks
20g USD 1650 2 Weeks
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Related CAS #: 7061-54-3 (dihydrate)   60-81-1,  

Synonym: Floridzin; phloridzin; phloretin-2'-β-D-glucopyranoside; AI3-19835; NSC 2833; NSC2833; NSC-2833; Phloretin 2'-glucoside; Phloretin-2'-O-beta-glucoside; Phlorizoside; Phlorrhizin.

IUPAC/Chemical Name: 1-[2,4-Dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-3-(4-hydroxyphenyl)propan-1-one

InChi Key: IOUVKUPGCMBWBT-GHRYLNIYSA-N

InChi Code: InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19-,20-,21-/m1/s1

SMILES Code: O=C(C1=C(O[C@H]2[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O2)C=C(O)C=C1O)CCC3=CC=C(O)C=C3

Appearance: White to light yellow solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Phlorizin is a white to yellow crystalline solid with a melting point of 106–109 °C. It is of sweet taste and contains four molecules of water in the crystal. Above 200 °C, it decomposes. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Upon prolonged exposure to aqueous solutions phlorizin hydrolyzes to phloretin and glucose. Phlorizin is not an effective drug because when orally consumed, it is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine. Phlorizin is found primarily in unripe Malus (apple), root bark of apple, trace amounts have been found in strawberry. In Malus, it is most abundant in vegetative tissues (such as leaves and bark) and seeds. Closely related species, such as pear (Pyrus communis), cherry, and other fruit trees in the Rosaceae do not contain phloridzin. Phloridzin is a phytochemical that belongs to the class of polyphenols. In natural sources, it may occur with other polyphenols such as quercetin, catechin, epicatechin, procyanidins, and rutin. (https://en.wikipedia.org/wiki/Phlorizin)

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 436.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Mei X, Zhang X, Wang Z, Gao Z, Liu G, Hu H, Zou L, Li X. Insulin Sensitivity-Enhancing Activity of Phlorizin Is Associated with Lipopolysaccharide Decrease and Gut Microbiota Changes in Obese and Type 2 Diabetes (db/db) Mice. J Agric Food Chem. 2016 Oct 12;64(40):7502-7511. Epub 2016 Sep 27. PubMed PMID: 27635781.

2: Pei F, Li BY, Zhang Z, Yu F, Li XL, Lu WD, Cai Q, Gao HQ, Shen L. Beneficial effects of phlorizin on diabetic nephropathy in diabetic db/db mice. J Diabetes Complications. 2014 Sep-Oct;28(5):596-603. doi: 10.1016/j.jdiacomp.2014.04.010. Epub 2014 Apr 24. PubMed PMID: 24927646.

3: Zhai Y, Dang Y, Gao W, Zhang Y, Xu P, Gu J, Ye X. P38 and JNK signal pathways are involved in the regulation of phlorizin against UVB-induced skin damage. Exp Dermatol. 2015 Apr;24(4):275-9. doi: 10.1111/exd.12642. Epub 2015 Mar 6. PubMed PMID: 25611805.

4: Shin SK, Cho SJ, Jung UJ, Ryu R, Choi MS. Phlorizin Supplementation Attenuates Obesity, Inflammation, and Hyperglycemia in Diet-Induced Obese Mice Fed a High-Fat Diet. Nutrients. 2016 Feb 16;8(2):92. doi: 10.3390/nu8020092. PubMed PMID: 26891322; PubMed Central PMCID: PMC4772055.

5: Hirose M, Shibazaki T, Nakada T, Kashihara T, Yano S, Okamoto Y, Isaji M, Matsushita N, Taira E, Yamada M. Phlorizin prevents electrically-induced ventricular tachyarrhythmia during ischemia in langendorff-perfused guinea-pig hearts. Biol Pharm Bull. 2014;37(7):1168-76. PubMed PMID: 24989008.

6: Zhang SY, Li BY, Li XL, Cheng M, Cai Q, Yu F, Wang WD, Tan M, Yan G, Hu SL, Gao HQ. Effects of phlorizin on diabetic retinopathy according to isobaric tags for relative and absolute quantification-based proteomics in db/db mice. Mol Vis. 2013 Apr 5;19:812-21. Print 2013. PubMed PMID: 23592918; PubMed Central PMCID: PMC3626294.

7: Wang X, Zhang S, Liu Y, Spichtig D, Kapoor S, Koepsell H, Mohebbi N, Segerer S, Serra AL, Rodriguez D, Devuyst O, Mei C, Wüthrich RP. Targeting of sodium-glucose cotransporters with phlorizin inhibits polycystic kidney disease progression in Han:SPRD rats. Kidney Int. 2013 Nov;84(5):962-8. doi: 10.1038/ki.2013.199. Epub 2013 May 29. PubMed PMID: 23715121.

8: Nagata T, Suzuki M, Fukazawa M, Honda K, Yamane M, Yoshida A, Azabu H, Kitamura H, Toyota N, Suzuki Y, Kawabe Y. Competitive inhibition of SGLT2 by tofogliflozin or phlorizin induces urinary glucose excretion through extending splay in cynomolgus monkeys. Am J Physiol Renal Physiol. 2014 Jun 15;306(12):F1520-33. doi: 10.1152/ajprenal.00076.2014. Epub 2014 Apr 23. PubMed PMID: 24761001.

9: Katsuda Y, Sasase T, Tadaki H, Mera Y, Motohashi Y, Kemmochi Y, Toyoda K, Kakimoto K, Kume S, Ohta T. Contribution of hyperglycemia on diabetic complications in obese type 2 diabetic SDT fatty rats: effects of SGLT inhibitor phlorizin. Exp Anim. 2015;64(2):161-9. doi: 10.1538/expanim.14-0084. Epub 2015 Jan 22. PubMed PMID: 25736710; PubMed Central PMCID: PMC4427731.

10: Makarova E, Górnaś P, Konrade I, Tirzite D, Cirule H, Gulbe A, Pugajeva I, Seglina D, Dambrova M. Acute anti-hyperglycaemic effects of an unripe apple preparation containing phlorizin in healthy volunteers: a preliminary study. J Sci Food Agric. 2015 Feb;95(3):560-8. doi: 10.1002/jsfa.6779. Epub 2014 Jul 4. PubMed PMID: 24917557.

11: Kashiwagi Y, Nagoshi T, Yoshino T, Tanaka TD, Ito K, Harada T, Takahashi H, Ikegami M, Anzawa R, Yoshimura M. Expression of SGLT1 in Human Hearts and Impairment of Cardiac Glucose Uptake by Phlorizin during Ischemia-Reperfusion Injury in Mice. PLoS One. 2015 Jun 29;10(6):e0130605. doi: 10.1371/journal.pone.0130605. eCollection 2015. PubMed PMID: 26121582; PubMed Central PMCID: PMC4486720.

12: Lijia X, Guo J, Chen Q, Baoping J, Zhang W. Quantitation of phlorizin and phloretin using an ultra high performance liquid chromatography-electrospray ionization tandem mass spectrometric method. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jun 1;960:67-72. doi: 10.1016/j.jchromb.2014.04.007. Epub 2014 Apr 13. PubMed PMID: 24786222.

13: Raja M, Kinne RK. Identification of phlorizin binding domains in sodium-glucose cotransporter family: SGLT1 as a unique model system. Biochimie. 2015 Aug;115:187-93. doi: 10.1016/j.biochi.2015.06.003. Epub 2015 Jun 15. PubMed PMID: 26086341.

14: Shen L, You BA, Gao HQ, Li BY, Yu F, Pei F. Effects of phlorizin on vascular complications in diabetes db/db mice. Chin Med J (Engl). 2012 Oct;125(20):3692-6. PubMed PMID: 23075726.

15: Chang WT, Huang WC, Liou CJ. Evaluation of the anti-inflammatory effects of phloretin and phlorizin in lipopolysaccharide-stimulated mouse macrophages. Food Chem. 2012 Sep 15;134(2):972-9. doi: 10.1016/j.foodchem.2012.03.002. Epub 2012 Mar 7. PubMed PMID: 23107715.

16: Choi HR, Nam KM, Lee HS, Yang SH, Kim YS, Lee J, Date A, Toyama K, Park KC. Phlorizin, an Active Ingredient of Eleutherococcus senticosus, Increases Proliferative Potential of Keratinocytes with Inhibition of MiR135b and Increased Expression of Type IV Collagen. Oxid Med Cell Longev. 2016;2016:3859721. doi: 10.1155/2016/3859721. Epub 2016 Mar 6. PubMed PMID: 27042261; PubMed Central PMCID: PMC4799823.

17: Lu WD, Li BY, Yu F, Cai Q, Zhang Z, Yin M, Gao HQ. Quantitative proteomics study on the protective mechanism of phlorizin on hepatic damage in diabetic db/db mice. Mol Med Rep. 2012 May;5(5):1285-94. doi: 10.3892/mmr.2012.803. Epub 2012 Feb 21. PubMed PMID: 22367743.

18: Hamouda NN, Qureshi MA, Alkaabi JM, Oz M, Howarth FC. Reduction in the amplitude of shortening and Ca(2+) transient by phlorizin and quercetin-3-O-glucoside in ventricular myocytes from streptozotocin-induced diabetic rats. Physiol Res. 2016 Jun 20;65(2):239-50. Epub 2015 Oct 8. PubMed PMID: 26447513.

19: Huang WC, Chang WT, Wu SJ, Xu PY, Ting NC, Liou CJ. Phloretin and phlorizin promote lipolysis and inhibit inflammation in mouse 3T3-L1 cells and in macrophage-adipocyte co-cultures. Mol Nutr Food Res. 2013 Oct;57(10):1803-13. doi: 10.1002/mnfr.201300001. Epub 2013 Jun 17. PubMed PMID: 23776070.

20: Brouwers B, Pruniau VP, Cauwelier EJ, Schuit F, Lerut E, Ectors N, Declercq J, Creemers JW. Phlorizin pretreatment reduces acute renal toxicity in a mouse model for diabetic nephropathy. J Biol Chem. 2013 Sep 20;288(38):27200-7. doi: 10.1074/jbc.M113.469486. Epub 2013 Aug 11. PubMed PMID: 23940028; PubMed Central PMCID: PMC3779717.