ChemicalBook >> CAS DataBase List >>Phlorizin

Phlorizin

CAS No.
60-81-1
Chemical Name:
Phlorizin
Synonyms
NSC 2833;Floridzin;PHLORIZIN;Phlorinin;phlorhizin;phlorizine;PHLORIDZIN;phloridzine;phlorrhizin;Phlorrhizen
CBNumber:
CB0331801
Molecular Formula:
C21H24O10
Molecular Weight:
436.41
MDL Number:
MFCD00006591
MOL File:
60-81-1.mol
MSDS File:
SDS
Last updated:2024-11-05 19:05:58

Phlorizin Properties

Melting point 113-114 °C(lit.)
Boiling point 468.89°C (rough estimate)
Density 1.3178 (rough estimate)
refractive index -54 ° (C=3.2, 95% EtOH)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka 7.15±0.40(Predicted)
color Light Yellow to Tan
Merck 14,7327
InChIKey IOUVKUPGCMBWBT-LKLLPNDVNA-N
SMILES C(C1C(=CC(O)=CC=1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)(=O)CCC1C=CC(O)=CC=1 |&1:9,10,11,13,15,r|
LogP 0.452 (est)
CAS DataBase Reference 60-81-1(CAS DataBase Reference)
FDA UNII CU9S17279X
EPA Substance Registry System Phlorizin (60-81-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  UC2080000
3-10-23
HS Code  29389090
NFPA 704
0
2 0

Phlorizin price More Price(52)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHL80513 Phloridzin phyproof? Reference Substance 60-81-1 100mg $266 2024-03-01 Buy
Sigma-Aldrich CDS000104 Phlorizin hydrate AldrichCPR 60-81-1 100MG $61.6 2023-06-20 Buy
Cayman Chemical 11576 Phlorizin ≥98% 60-81-1 1g $73 2024-03-01 Buy
Cayman Chemical 11576 Phlorizin ≥98% 60-81-1 5g $324 2024-03-01 Buy
Cayman Chemical 11576 Phlorizin ≥98% 60-81-1 10g $575 2024-03-01 Buy
Product number Packaging Price Buy
PHL80513 100mg $266 Buy
CDS000104 100MG $61.6 Buy
11576 1g $73 Buy
11576 5g $324 Buy
11576 10g $575 Buy

Phlorizin Chemical Properties,Uses,Production

Summary

Phlorizin is the glucoside of phloretin. Its chemical name is 1- (2- (beta-D- glucopyranose oxygroup) -46- dihydroxy phenyl) -3- (4- hydroxycyclohexyl phenyl ketone) acetone, which belongs to dihydrochlcone of flavonoid. Phloridzin mainly exists in root barks, stems, leaflets and fruit of the apple tree, it can also be found in small amounts in the plants such as compositae, leguminosae, fagaceae, ericaceae, liliaceae and so on. It has many important biological activities, such as reducing blood sugar, improving memory, anti-allergy, anticancer, etc., as well as potential use values in food, beauty and health care products and other industry.

Distribution

Phloridzin exists mainly in Malus of Rosace, it has been reported in plants such as compositae, leguminosae, fagaceae, ericaceae, liliaceae and so on, but their amount is very low. In recent years, phlorizin is also found in litchi peel, leaves of pyrus betulaefolia, cynomorium songaricum, etc. though with a small amount. However, there are plenty of phloridzin in Lilhocarpus Polystachys Rehd. In general, the Malus plants are the main source of glucoside and can be used as the raw material to extract glucoside. Phloridzin is rich in branches, leaflets and barks of the apple tree. It can The distribution of phloridzin in apple fruits concentrate in seeds and rinds. The apple branches, leaves, bark and so on contain a large number of glucoside. The distribution of glucoside in apple fruit is concentrated on seeds and pericarp.

Extraction method

  1. Material crushing: The dried branches or leaves of apple trees are crushed into coarse powders (10~20 mesh or 20~30 mesh).
  2. Extraction: Put pulverized crude powders into round flask, add 70% methanol for reflux extraction for 3 times, add 6, 4 and 4BV liquid independently, keep for 1h each time and combine the extracted solutions; (three extracts are brown to tan respectively).
  3. Inspissation: The antioxidant (VC) is added into the combined extract according to 0.2% of the total weight. Methanol can be recovered by reduced pressure distillation at 60℃.( The outcome solution is brownish turbid liquid)
  4. Removing impurities: Add polymerization alumina according to 0.5% of weight into the recovered concentrated solution without alcohol, adjust pH value to 7.5 with calcium hydroxide, put in the conical flask, hold 30min at 60℃, obtain the liquor after filtration; (flocculent is generated at the bottom after adding polymerization alumina)
  5. Extraction: the extraction condensate is cooled, the ethyl acetate is extracted with 1 times the ethyl acetate 3 times and the ethyl acetate solution is obtained; (the solution is stratified rapidly).
  6. Concentration: the ethyl acetate extract is decompressed and refluxed, concentrated to 10: 1, and the concentrated solution is obtained.
  7. Purification: Dissolve the concentrated liquid with 40% methanol, filter, place the filtrate for 24h, get the crystallization after extraction filtration, obtain the phlorizin by prevailing pressure drying or reducing pressure drying. (yellow powder) The activated carbon is used to decolorize the crude products because its decolorization principle is physical adsorption without damage to the biological activity of the root bark. The activated carbon is dried in a vacuum drying box to be activated. Then the activated carbon is added into aqueous solutions of crude products. The supernatant liquid can be obtained after stir and filtration. The liquid is placed to crystalize under natural conditions and the white needle crystal occurs eventually.
Figure 1. the p technological process of the phlorizin extractionFigure 1. the p technological process of the phlorizin extraction

Synthetic method

The precusor substance used to synthetize phlorizin is Malonyl-CoA and p-coumaroyl-CoA.
Firstly, we use p-coumaroyl-CoA to generate 4-hydroxydihydrocinnamoyl-CoA by NADPH; then, phloretin is synthesized by Malonyl-CoA and 4-hydroxydihydrocinnamoyl-CoA under the action of tecatone synthetase; finally, phloridzin is generated by phloretin glucosylation. The overviews, extraction methods and synthesis methods of the phlorizin are compiled by Shi yan of Chemicalbook. (2015-12-02)

Biological activity

  • Hypoglycemic effect
Diabetes is a major disease that threatens human health and its typical symptom is hyperglycemia. Now the main drugs for the treatment of diabetes include traditional sulfonylurea, metformin and some new hypoglycemic agents such as rosiglitazone, pioglitazone, etc. The mechanisms of action are mostly used to promote insulin secretion or increase insulin sensitivity. A large number of studies have shown that phlorizin has the effect of reducing fasting blood glucose. The mechanism of decreasing glucose is competitively inhibiting the transport of glucose molecules on glucose transporters (SGLTs and GLUTs).
  • Antioxidation
Phlorizin has obvious protective effects on oxidative damage induced by high-fat diet in drosophila, as well as strong antioxidant effect, and enhance the activity of SOD and CAT to prolong life spans of drosophila significantly.
  • The physiological relationship with plants.
Phlorizin is closely related to the growth and stress resistance and other physiological phenomena of plants. It can resist various pathogenic bacterias, such as apple scab, fire blight, etc. However, it may inhibit the growth of some plants. Low concentration of phlorizin can promote the growth of Pingyi sweet tea seedlings, but high concentration will cause plant replant disorders. Phlorizin can promote the regeneration of papaya embryos and stimulate the root growth particularly. Therefore, as a plant growth regulator, its dosage is the key factor.
  • Other activities
In addition to antidiabetics, antioxidant and other biological activities, phlorizin has effects of anti-inflammatory, anti-cancer and so on.  

Application

It has many important biological activities, such as reducing blood sugar, improving memory, anti allergy, anticancer, etc., as well as potential use values in food, beauty and health care products and other industry.

  • Food
Phlorizin has been approved as a kind of food additive. It is a characteristic phenolic substance in apple. Due to species, producers and other issues, the contents of phlorizin in different apples are quite different. Therefore, its content can be used as an index to distinguish the producers and qualities of apple juice. Phlorizin can promote the absorption and utilization of genistein (inhibit the growth and metastasis of tumor cells). It has a broad market in prevention and treatment of cancer to develop functional foods which rich in phlorizin and genistein. It is a high sweet natural sweetener, which can be used as an alternative food for diabetic patients. After phlorizin is oxidized by polyphenol oxidase, the products can be converted into bright yellow dyes. The dye has strong water solubility and can be used in food processing industry instead of artificial dyes to avoid the toxic effects caused by synthetic pigments. It has potential application values in the development and utilization either as a kind of food additive or as a functional food.
  • Medicine
As phlorizin is easily hydrolyzed in human body to yield the phloretin and has lower intestinal absorption rate, it is often designed to be high molecular polymer for the development of drugs with other compounds.
  • Cosmetics
The antioxidant activity and antiaging function of phlorizin have been confirmed by modern scientific researches. The hydrolysate of phlorizin, which is called phloretin, can inhibit the tyrosinase activity competitively and interfere the synthesis of melanin. Its whitening effect is better than many whitening products on the market. However, it is important to note that phlorizin increases the expression of tyrosinase genes by activating the cAMP signaling pathway, which leads to the formation of melanin.

Chemical Properties

Light Yellow Powder

Uses

induces experimental glucosuria, antifeedant

Uses

It is a dihydrochalcone occurring in all parts of the apple tree except the mature fruit. Once thought to occur in pear, plum, cherry trees and other Rosaceae

Uses

Sodium-glucose cotransporter 1 (SGLT1) is a high affinity, low capacity transporter abundant in the small intestine, with some expression in the kidney as well. SGLT2 is a low affinity, high capacity transporter in the kidney that accounts for approximately 90% of glucose reabsorption into the blood stream. Selective inhibition of SGLT2 is a potential strategy for reducing plasma glucose levels as a treatment for diabetes. Phlorizin is a natural product, first isolated from the bark of apple trees, that reduces plasma glucose levels by blocking renal and intestinal glucose absorption through inhibition of SGLT1 and SGLT2. It competitively inhibits the initial rate of a-methyl-D-glucopyranoside (a-MDG) uptake in human COS-1 cells expressing hSGLT1 and hSGLT2 with IC50 values of 400 and 65 nM, respectively. In HEK293T cells expressing human SGLT1 and SGLT2, phlorizin exhibits Ki values of 140 and 11 nM, respectively, at 37°C.

Definition

ChEBI: An aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 2' via a glycosidic linkage.

Purification Methods

-D-glucoside] [60-81-1] M 472.5, m 110o, [] 20 -62o (c 3.2, EtOH). Phlorizin crystallises as the dihydrate from water and causes glycosuria. [Brazy & Dennis Am J Physiol 234 1279 1978, Zemplen & Bognár Chem Ber 17B 1040 1943, Beilstein 17/7 V 177.]

Phlorizin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 337)Suppliers
Supplier Tel Email Country ProdList Advantage
Shaanxi LonierHerb Bio Technology Co Ltd
+86-86-+86-86-029-87551862 +8617702909819 sales006@ingredients-lonier.com China 2604 58
Hebei Kingfiner Technology Development Co.Ltd
+86-15532196582 +86-15373005021 lisa@kingfinertech.com China 2990 58
Hebei Saisier Technology Co., LTD
+86-18400010335 +86-18034520335 admin@hbsaisier.cn China 1015 58
Shaanxi TNJONE Pharmaceutical Co., Ltd
+8618092446649 sarah@tnjone.com China 1143 58
Hebei Longbang Technology Co., LTD
+86-18633929156 +86-18633929156 admin@hblongbang.com China 941 58
HebeiShuoshengImportandExportco.,Ltd
+86-18532138899 +86-18532138899 L18532138899@163.com China 939 58
Hangzhou FandaChem Co.,Ltd.
+8615858145714 FandaChem@Gmail.com China 9215 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32951 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3619 58
career henan chemical co
+86-0371-86658258 +8613203830695 sales@coreychem.com China 29885 58

Related articles

  • Biological activity of Phlorizin
  • Phloridzin has many biological activities such asreducing blood sugar, improving memory, anti allergy, anticancer, etc., as we....
  • Nov 2,2022

View Lastest Price from Phlorizin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Phlorizin pictures 2024-11-08 Phlorizin
60-81-1
US $6.00 / kg 1kg 99% 2000KG/Month HebeiShuoshengImportandExportco.,Ltd
Phlorizin pictures 2024-11-08 Phlorizin
60-81-1
US $200.00-195.00 / kg 1kg 98%,50%Phloretin : 70%, 80%, 90%, 98% 100000 Changsha Staherb Natural Ingredients Co., Ltd.
Phlorizin pictures 2024-11-07 Phlorizin
60-81-1
US $6.00 / kg 1kg More than 99% 2000KG/Month Hebei Longbang Technology Co., Ltd
  • Phlorizin pictures
  • Phlorizin
    60-81-1
  • US $6.00 / kg
  • 99%
  • HebeiShuoshengImportandExportco.,Ltd
  • Phlorizin pictures
  • Phlorizin
    60-81-1
  • US $200.00-195.00 / kg
  • 98%,50%Phloretin : 70%, 80%, 90%, 98%
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • Phlorizin pictures
  • Phlorizin
    60-81-1
  • US $6.00 / kg
  • More than 99%
  • Hebei Longbang Technology Co., Ltd
1-propanone,1-(2-(beta-d-glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyp phlorhizin phloridzine phlorizine phlorizoside 1-Propanone, 1-[2-(β-D-glucopyranosyloxy)- 4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)- Floridzin 1-(2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-propan-1-on phlorrhizin TIMTEC-BB SBB005924 PHLORIZIN HYDRATE PHLORETIN-2'-BETA-D-GLUCOPYRANOSIDE DIHYDRATE PHLORETIN-2'-BETA-D-GLUCOSIDE PHLORETIN 2'-BETA-D-GLUCOSIDE DIHYDRATE PHLORETIN-2'-O-GLUCOSIDE DIHYDRATE PHLORIDZIN PHLORIDZIN DIHYDRATE PHLORIZIN 4',6'-DIHYDROXY-2'-(BETA-D-GLUCOSIDO)-3-(4-HYDROXYPHENYL) PROPIOPHENONE 1-[2-(BETA-D-GLUCOPYRANOSYLOXY)-4,6-DIHYDROXYPHENYL]-3-(4-HYDROXYPHENYL)-1-PROPANONE 2'-O-GLUCOSYL-4',6',4-TRIHYDROXYDIHYDROCHALCONE 2'-O-GLUCOSYL-4',6',4-TRIHYDROXYDIHYDROCHALCONE DIHYDRATE 2'-(beta-D-glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenone 1-[2-(b-D-Glucopyranosyl-oxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone Phloretin-2b-glucosid Phlorrhizen 1-(2-(beta-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-propan-1-on phloridzosid PHLORIDZIN(P) 1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyMethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one Phlorizin(Phloridzin) 1-Propanone, 1-[2-(β-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)- Phlorizin 60-81-1 Phloridzin n-Hydrate, from Apple NSC 2833 Phlorizin,>98% Phlorinin hot selling phloridzin Phlorizin (Floridzin 2'-(beta-D-glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyph... 1-Propanone,1-[2-(b-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)- 1-(2,4-Dihydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one Phloretin 2'-O-β-D-glucoside Apple Root Extract Phlorizin Floridzin|||NSC 2833|||Phloridzin Allyl Amyl Glycolate,Isogalbanate Phloridzin-RM 60-81-1 C21H24O10xH2O C21H24O10 C21H24O10H2O Glycosides Sugars Analytical Chromatography Product Catalog BioChemical Biochemicals and Reagents Analytical Standards