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Phlorizin dihydrate

CAS# 7061-54-3

Phlorizin dihydrate

Catalog No. BCN2584----Order now to get a substantial discount!

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Chemical structure

Phlorizin dihydrate

3D structure

Chemical Properties of Phlorizin dihydrate

Cas No. 7061-54-3 SDF Download SDF
PubChem ID 9912668 Appearance Powder
Formula C21H28O12 M.Wt 472.44
Type of Compound Chalcones Storage Desiccate at -20°C
Synonyms Phloridzin dihydrat
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one;dihydrate
SMILES C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)O.O.O
Standard InChIKey XQWBNXSENPTIDY-YXMARJSJSA-N
Standard InChI InChI=1S/C21H24O10.2H2O/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;2*1H2/t16-,18-,19+,20-,21-;;/m1../s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Phlorizin dihydrate

The herbs of Prunus armeniaca L.

Biological Activity of Phlorizin dihydrate

DescriptionPhlorizin dihydrate can significantly inhibit oxidative DNA damage.
TargetsNO | PGE | NOS | COX
In vitro

Crystal structure of phlorizin and the iodothyronine deiodinase inhibitory activity of phloretin analogues[Reference: WebLink]

Biochemical Pharmacology Volume 35, Issue 13, 1 July 1986, Pages 2221–2227

Phloretin, a 7,8-dihydrochalcone of plant origin, and the high molecular weight (<15,000) polyphloretinphosphate (PPP) polymers are potent inhibitors of iodothyronine monodeiodinase activity from rat liver microsomal preparations, whereas phlorizin, the 2′-O-glucoside of phloretin, is inactive.
METHODS AND RESULTS:
The polymers, differing in degree of phosphorylation-dependent polymerization, exhibited a concentration-dependent, and ultimately complete, inhibition of deiodinase activity with an IC50 between 0.2 and 0.5 μg PPP/ml. Phloretin inhibition, on the other hand, was cofactor (DTE) competetive, with a Ki = 0.75 μM. 2′,4′,6′,3,4-Pentahydroxychalcone, which has a substitution pattern in the A-ring identical to that of phloretin, was the only active inhibitor (IC50= 8 μM) among several derivatives tested. The phloretin biodegradation products, phloretic acid and phloroglucinol, and its biosynthetic precursors, monomeric cinnamic acid and cinnamic acid derivatives, were inactive in concentrations up to 100 μM. The X-ray crystal structure analysis of Phlorizin dihydrate showed that the molecule is planar and fully extended, similar to the conformation observed in chalcone structures that are characterized by an α, β-unsaturated bond between phenol rings.
CONCLUSIONS:
Comparison of the planar phlorizin crystal structure with a skewed or antiskewed thyroid hormone conformation revealed that the β-D-glucose moiety does not share any of the thyroid hormone's conformational space, and that the best structural homology is found with the antiskewed conformation of 3′,5′,3-triiodothyronine, the natural deiodinase substrate that also inhibits further deiodination.

Inhibitory Effect of the Phenolic Compounds from Apples Against Oxidative Damage and Inflammation[Reference: WebLink]

Korean Journal of Plant Resources Vol.23 No.6, 2010.12, 487-497

ROS have been associated with pathogenic processes including carcinogenesis through direct effect on DNA and play an important role in the pathogenesis of inflammation. Because of many types of phenolic acid derivatives and flavonoids, apples have been one of the human diet since ancient times and are one of the most commonly consumed fruits in worldwide.
METHODS AND RESULTS:
In this study, catechin, chlorogenic acid and Phlorizin dihydrate were purified and identified by HPLC and GC/MS. The contents of catechin, chlorogenic acid and Phlorizin dihydrate were 1.01 ㎎, 7.01 ㎎ and 3.67 ㎎/ ㎏ wet weight, respectively. Catechin and Phlorizin dihydrate were found to significantly inhibit oxidative DNA damage, while chlorogenic did not affect. Also, catechin inhibits NO and PGE₂ production via suppressing iNOS and COX-2 expression. However, chlorogenic acid and Phlorizin dihydrate did not affect.
CONCLUSIONS:
Our results show that catechin may be the most active phenolic compound in anti-oxidative damage and anti-inflammatory effect.

Phlorizin dihydrate Dilution Calculator

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Phlorizin dihydrate Molarity Calculator

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Preparing Stock Solutions of Phlorizin dihydrate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1167 mL 10.5834 mL 21.1667 mL 42.3334 mL 52.9168 mL
5 mM 0.4233 mL 2.1167 mL 4.2333 mL 8.4667 mL 10.5834 mL
10 mM 0.2117 mL 1.0583 mL 2.1167 mL 4.2333 mL 5.2917 mL
50 mM 0.0423 mL 0.2117 mL 0.4233 mL 0.8467 mL 1.0583 mL
100 mM 0.0212 mL 0.1058 mL 0.2117 mL 0.4233 mL 0.5292 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Phlorizin dihydrate

Crystal structure of phlorizin and the iodothyronine deiodinase inhibitory activity of phloretin analogues.[Pubmed:3729977]

Biochem Pharmacol. 1986 Jul 1;35(13):2221-7.

Phloretin, a 7,8-dihydrochalcone of plant origin, and the high molecular weight (less than 15,000) polyphloretinphosphate (PPP) polymers are potent inhibitors of iodothyronine monodeiodinase activity from rat liver microsomal preparations, whereas phlorizin, the 2'-O-glucoside of phloretin, is inactive. The polymers, differing in degree of phosphorylation-dependent polymerization, exhibited a concentration-dependent, and ultimately complete, inhibition of deiodinase activity with an IC50 between 0.2 and 0.5 micrograms PPP/ml. Phloretin inhibition, on the other hand, was cofactor (DTE) competitive, with a Ki = 0.75 microM. 2',4',6',3,4- Pentahydroxychalcone, which has a substitution pattern in the A-ring identical to that of phloretin, was the only active inhibitor (IC50 = 8 microM) among several derivatives tested. The phloretin biodegradation products, phloretic acid and phloroglucinol, and its biosynthetic precursors, monomeric cinnamic acid and cinnamic acid derivatives, were inactive in concentrations up to 100 microM. The X-ray crystal structure analysis of Phlorizin dihydrate showed that the molecule is planar and fully extended, similar to the conformation observed in chalcone structures that are characterized by an alpha, beta-unsaturated bond between phenol rings. Comparison of the planar phlorizin crystal structure with a skewed or antiskewed thyroid hormone conformation revealed that the beta-D-glucose moiety does not share any of the thyroid hormone's conformational space, and that the best structural homology is found with the antiskewed conformation of 3',5',3-triiodothyronine, the natural deiodinase substrate that also inhibits further deiodination.

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