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Phlorizin

Item № 11576
CAS № 60-81-1
Purity ≥98%
product image
                (CAS 60-81-1)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 g $56.00 0.00
     5 g $252.00 0.00
     10 g $448.00 0.00

Pricing updated 2019-07-17. Prices are subject to change without notice.

Description
Synonyms
  • Floridzin
  • NSC 2833

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.1 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 SGLT2.2,3 It competitively inhibits the initial rate of α-methyl-D-glucopyranoside (α-MDG) uptake in human COS-1 cells expressing hSGLT1 and hSGLT2 with IC50 values of 400 and 65 nM, respectively.4 In HEK293T cells expressing human SGLT1 and SGLT2, phlorizin exhibits Ki values of 140 and 11 nM, respectively, at 37°C.4,5

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Technical Information
Formal Name
1-[2-(β-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
CAS Number
60-81-1
Synonyms
  • Floridzin
  • NSC 2833
Molecular Formula
C21H24O10
Formula Weight
436.4
Purity
≥98%
Formulation
A crystalline solid
λmax
224, 285 nm
SMILES
O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](OC2=CC(O)=CC(O)=C2C(CCC3=CC=C(O)C=C3)=O)[C@@H]1O
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
InChI Key
IOUVKUPGCMBWBT-QNDFHXLGSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

1. Chao, E.C., and Henry, R.R. SGLT2 inhibition - A novel strategy for diabetes treatment Nature Reviews.Drug Discovery 9(7), 551-559 (2010).

2. White, J.R., Jr. Apple trees to sodium glucose co-transporter inhibitors: A review of SGLT2 inhibition Clinical Diabetes 28(1), 5-10 (2010).

3. Ehrenkranz, J.R.L., Lewis, N.G., Kahn, C.R., et al. Phlorizin: A review Diabetes/Metabolism Research and Reviews 21, 31-38 (2005).

4. Hummel, C.S., Lu, C., Liu, J., et al. Structural selectivity of human SGLT inhibitors American Journal of Physiology.Cell Physiology 302(2), C373-C382 (2012).

5. Hummel, C.S., Lu, C., Loo, D.D.F., et al. Glucose transport by human renal Na+/D-glucose cotransporters SGLT1 and SGLT2 American Journal of Physiology.Cell Physiology 300, C14-C21 (2011).

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