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Phlorizin

Phlorizin structure

CAS No:
60-81-1
Formula:
C21H24O10
Chemical Name:
Phlorizin
Synonyms:
1-propanone,1-(2-(beta-d-glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyp;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
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

Phlorizin is a non-selective SGLT inhibitor with Kis of 300 and 39 nM for hSGLT1 and hSGLT2, respectively. Phlorizin is also a Na+/K+-ATPase inhibitor.

Solid

Phlorizin is an aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 2' via a glycosidic linkage. It has a role as a plant metabolite and an antioxidant. It is an aryl beta-D-glucoside, a member of dihydrochalcones and a monosaccharide derivative. It derives from a phloretin.

Light Yellow Powder

-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 Basic Attributes

Molecular Weight：

436.41

Exact Mass：

436.41

EC Number：

200-487-1

UNII：

CU9S17279X

DSSTox ID：

DTXSID3075339

Color/Form：

Light Yellow to Tan

HScode：

29389090

Characteristics

PSA：

177

XLogP3：

1.2

Appearance：

Solid

Density：

1.3178 (rough estimate)

Melting Point：

113-114 °C(lit.)

Boiling Point：

468.89°C (rough estimate)

Flash Point：

270.7±26.4 °C

Refractive Index：

-54 ° (C=3.2, 95% EtOH)

Water Solubility：

1 mg/mL at 22 °C

Storage Conditions：

2-8°C

PKA：

7.15±0.40(Predicted)

Collision Cross Section：

194.4 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Critical Temperature & Pressure：

Keep in dark place,Sealed in dry,Room Temperature

Safety Information

wgk germany：

hazard class code：

safety instructions：

26-36

RTECS Number：

UC2080000

Marks：

Hazard Statements：

36/37/38

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 69 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

Phlorhizin

Phlorizin Use and Manufacturing

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.

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

induces experimental glucosuria, antifeedant

Computed Properties

Molecular Weight:436.4
XLogP3:1.2
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:7
Exact Mass:436.13694696
Monoisotopic Mass:436.13694696
Topological Polar Surface Area:177
Heavy Atom Count:31
Complexity:581
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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