Phlorizin | CAS#60-81-1 | Glucoside

MedKoo Cat#: 329650 | Name: Phlorizin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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 Phlorizin was studied as a potential pharmaceutical treatment for type 2 diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as canagliflozin and dapagliflozin.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

Phlorizin

CAS#60-81-1

Theoretical Analysis

MedKoo Cat#: 329650

Name: Phlorizin

CAS#: 60-81-1

Chemical Formula: C21H24O10

Exact Mass: 436.1369

Molecular Weight: 436.41

Elemental Analysis: C, 57.80; H, 5.54; O, 36.66

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 weeks
5g	USD 550.00	2 weeks
10g	USD 850.00	2 weeks
25g	USD 1,650.00	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)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Phlorizin is a non-selective SGLT inhibitor with Kis of 300 and 39 nM for hSGLT1 and hSGLT2.

In vitro activity:

In vitro studies also confirmed the activity of phlorizin against CP BVDV. Exploration on its potential mechanism suggested that phlorizin inhibited CP BVDV-induced beclin-1 level and the conversion rate of LC3B-I to LC3B-II. Interestingly, although phlorizin also showed a protective effect on MDBK cells, which were treated with 3-methyladenine A (3-MA), the effect was significantly weakened. Furthermore, phlorizin suppressed the stage of BVDV replication but showed no effect on stages of attachment and internalization. Reference: J Agric Food Chem. 2022 Nov 30;70(47):14841-14850. https://pubmed.ncbi.nlm.nih.gov/36384297/

In vivo activity:

In the present study, blood glucose levels of female SDT fatty rats were controlled with phlorizin, a non-selective SGLT inhibitor, to examine whether and how these complications are caused by hyperglycemia. Phlorizin treatment adequately controlled plasma glucose levels during the experiment. These renal parameters tended to decrease with phlorizin; however, effects were partial. Sciatic nerve conduction velocities were significantly delayed in SDT fatty rats compared with Sprague-Dawley (SD) rats. Both nerve and eye disorders were prevented with phlorizin. Reference: Exp Anim. 2015;64(2):161-9. https://pubmed.ncbi.nlm.nih.gov/25736710/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	68.74
	DMSO	40.0	91.66
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.15
	Ethanol	5.0	11.46
	Water	1.0	2.29

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

1. Zhang Z, Huang J, Zhao Z, Yuan X, Li C, Liu S, Cui Y, Liu Y, Zhou Y, Zhu Z. In Vivo and In Vitro Antiviral Activity of Phlorizin Against Bovine Viral Diarrhea Virus. J Agric Food Chem. 2022 Nov 30;70(47):14841-14850. doi: 10.1021/acs.jafc.2c05934. Epub 2022 Nov 16. PMID: 36384297. 2. Jia Z, Xie Y, Wu H, Wang Z, Li A, Li Z, Yang Z, Zhang Z, Xing Z, Zhang X. Phlorizin from sweet tea inhibits the progress of esophageal cancer by antagonizing the JAK2/STAT3 signaling pathway. Oncol Rep. 2021 Jul;46(1):137. doi: 10.3892/or.2021.8088. Epub 2021 May 26. PMID: 34036398; PMCID: PMC8165578. 36384297. 3. 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. PMID: 25736710; PMCID: PMC4427731. 4. Rossetti L, Smith D, Shulman GI, Papachristou D, DeFronzo RA. Correction of hyperglycemia with phlorizin normalizes tissue sensitivity to insulin in diabetic rats. J Clin Invest. 1987 May;79(5):1510-5. doi: 10.1172/JCI112981. PMID: 3571496; PMCID: PMC424427.

In vitro protocol:

In vivo protocol:

1. 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. PMID: 25736710; PMCID: PMC4427731. 2. Rossetti L, Smith D, Shulman GI, Papachristou D, DeFronzo RA. Correction of hyperglycemia with phlorizin normalizes tissue sensitivity to insulin in diabetic rats. J Clin Invest. 1987 May;79(5):1510-5. doi: 10.1172/JCI112981. PMID: 3571496; PMCID: PMC424427.

1: Liu Z, Yang Y, Xu Y, Zhang Z, Tang R, Liu J, Jiang H, Zhao R. Procyanidin B1 and p-coumaric acid from whole highland barley ameliorated HFD-induced impaired glucose tolerance via small intestinal barrier and hepatic glucose metabolism. Food Funct. 2024 Aug 20. doi: 10.1039/d4fo02805h. Epub ahead of print. PMID: 39162187. 2: Yang Y, Ma S, Li A, Xia G, Li M, Ding C, Sun X, Yan L, Yang M, Zhao T. Antibacterial and antioxidant phlorizin-loaded nanofiber film effectively promotes the healing of burn wounds. Front Bioeng Biotechnol. 2024 Aug 5;12:1428988. doi: 10.3389/fbioe.2024.1428988. PMID: 39161349; PMCID: PMC11330827. 3: Almalki A, Arjun S, Harding I, Jasem H, Kolatsi-Joannou M, Jafree DJ, Pomeranz G, Long DA, Yellon DM, Bell RM. SGLT1 contributes to glucose-mediated exacerbation of ischemia-reperfusion injury in ex vivo rat heart. Basic Res Cardiol. 2024 Aug 1. doi: 10.1007/s00395-024-01071-z. Epub ahead of print. PMID: 39088085. 4: Yao Y, Zhong Q, Zhong Y, Gao Z, Zhou B, Lu C, Zheng L, Yin F, Tan M. Integrating network pharmacology and experimental verification to explore the pharmacological mechanisms of phlorizin against osteoarthritis. Naunyn Schmiedebergs Arch Pharmacol. 2024 Aug 1. doi: 10.1007/s00210-024-03324-z. Epub ahead of print. PMID: 39085510. 5: Fernando W, MacLean E, Monro S, Power Coombs MR, Marcato P, Rupasinghe HPV, Hoskin DW. Phloridzin Docosahexaenoate, an Omega-3 Fatty Acid Ester of a Flavonoid Precursor, Inhibits Angiogenesis by Suppressing Endothelial Cell Proliferation, Migration, and Differentiation. Biomolecules. 2024 Jun 27;14(7):769. doi: 10.3390/biom14070769. PMID: 39062483; PMCID: PMC11274491. 6: Meganathan MK, Ramalingam S. Green Nanoengineered Fabrics: Waste-Derived Polyphenol-Zinc@ Silica Core-Shell Reactive Janus Nanoparticles for Functional Fabrics. ACS Appl Mater Interfaces. 2024 Jul 31;16(30):40004-40017. doi: 10.1021/acsami.4c08268. Epub 2024 Jul 18. PMID: 39023009. 7: Damian-Medina K, Herrera-González A, Figueroa-Yáñez LJ, Arrizon J. Enzymatic Fructosylation of Phenolic Compounds: A New Alternative for the Development of Antidiabetic Drugs. Molecules. 2024 Jun 27;29(13):3072. doi: 10.3390/molecules29133072. PMID: 38999025; PMCID: PMC11243490. 8: Wu D, Hao L, Liu X, Li X, Zhao G. The Anti-Biofilm Properties of Phloretin and Its Analogs against Porphyromonas gingivalis and Its Complex Flora. Foods. 2024 Jun 24;13(13):1994. doi: 10.3390/foods13131994. PMID: 38998500; PMCID: PMC11241327. 9: Wang H, Jian L, Wang Z, Jiao Y, Wang Y, Ma F, Li P. Glycosylation mode of phloretin affects the morphology and stress resistance of apple plant. Plant Cell Environ. 2024 Jul 12. doi: 10.1111/pce.15031. Epub ahead of print. PMID: 38995178. 10: Deng J, Che X, Gu Y, Qu Y, Liu D. Integrated multi-omics investigation revealed the importance of phenylpropanoid metabolism in the defense response of Lilium regale Wilson to fusarium wilt. Hortic Res. 2024 May 20;11(7):uhae140. doi: 10.1093/hr/uhae140. PMID: 38988612; PMCID: PMC11233880. 11: Dai F, Lee SO, Song JH, Yoo WG, Shin EH, Bai X, Hong SJ. Glucose transporters and sodium glucose co-transporters cooperatively import glucose into energy-demanding organs in carcinogenic liver fluke Clonorchis sinensis. PLoS Negl Trop Dis. 2024 Jul 5;18(7):e0012315. doi: 10.1371/journal.pntd.0012315. PMID: 38968307; PMCID: PMC11253919. 12: Guo Q, Li TF, Huang J, Li JC, Zhang ZC, Qu YL. The protective role of phlorizin against lipopolysaccharide-induced acute orchitis in mice associated with changes in gut microbiota composition. Front Vet Sci. 2024 May 23;11:1340591. doi: 10.3389/fvets.2024.1340591. PMID: 38846786; PMCID: PMC11156221. 13: Egashira T, Ichinomiya T, Yokoyama A, Matsumoto S, Higashijima U, Sekino M, Murata H, Yoshitomi O, Sato S, Hara T. Cardioprotective Effects of Sodium- Glucose Cotransporter Subtype Inhibition on Ischemic and Pharmacological Preconditioning. Cureus. 2024 May 6;16(5):e59757. doi: 10.7759/cureus.59757. PMID: 38841006; PMCID: PMC11152766. 14: Zhao H, Zhai BW, Zhang MY, Huang H, Zhu HL, Yang H, Ni HY, Fu YJ. Phlorizin from Lithocarpus litseifolius [Hance] Chun ameliorates FFA-induced insulin resistance by regulating AMPK/PI3K/AKT signaling pathway. Phytomedicine. 2024 Jul 25;130:155743. doi: 10.1016/j.phymed.2024.155743. Epub 2024 May 15. PMID: 38824822. 15: Du P, Cao Y, Li J, Zhou S, Li Z, Zhang X, Xu J, Liang B. Dopamine Alleviates Phloridzin Toxicity in Apple by Modifying Rhizosphere Bacterial Community Structure and Function. J Agric Food Chem. 2024 Jun 12;72(23):13001-13014. doi: 10.1021/acs.jafc.4c02276. Epub 2024 May 29. PMID: 38812066. 16: Xu H, Zhang S, Liang C, Li M, Wang R, Song J, Cui Z, Yang Y, Liu J, Li D. Melatonin enhances resistance to Botryosphaeria dothidea in pear by promoting jasmonic acid and phlorizin biosynthesis. BMC Plant Biol. 2024 May 29;24(1):470. doi: 10.1186/s12870-024-05187-1. PMID: 38811892; PMCID: PMC11134937. 17: Zhang W, Sun Y, Wang H, Xu M, He C, Wang C, Yu Y, Zhang Z, Su L. Exogenous Melatonin Enhances Dihydrochalcone Accumulation in Lithocarpus litseifolius Leaves via Regulating Hormonal Crosstalk and Transcriptional Profiling. Int J Mol Sci. 2024 Apr 23;25(9):4592. doi: 10.3390/ijms25094592. PMID: 38731810; PMCID: PMC11083347. 18: Zeng S, Yu L, He P, Feng H, Wang J, Zhang H, Song Y, Liu R, Li Y. Integrated transcriptome and metabolome analysis reveals the regulation of phlorizin synthesis in Lithocarpus polystachyus under nitrogen fertilization. BMC Plant Biol. 2024 May 6;24(1):366. doi: 10.1186/s12870-024-05090-9. PMID: 38711037; PMCID: PMC11071233. 19: Wang L, Wu X, Wan Q, Yang Y, Gao C. Phlorizin Regulates Synovial Hyperplasia and Inflammation in Rats With Rheumatoid Arthritis by Regulating the mTOR Pathway. In Vivo. 2024 May-Jun;38(3):1182-1191. doi: 10.21873/invivo.13553. PMID: 38688626; PMCID: PMC11059876. 20: Sharma K, Ramachandran V, Sharma A, Mohanasundaram T, Mageshkumar H. Phloridzin's Diabetic Wound Healing Potential through DPP-4 Enzyme Inhibition: A Review Article. Curr Diabetes Rev. 2024 Apr 26. doi: 10.2174/0115733998291941240416053855. Epub ahead of print. PMID: 38676506.