Icariside I
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MedKoo CAT#: 463979

CAS#: 56725-99-6

Description: Icariside I is a flavonoid glycoside and an active metabolite of icariin that has been found in Epimedium and has osteogenic and anticancer activities. It is formed from icariin in rats by intestinal microbiota. It stimulates the proliferation and differentiation of isolated rat osteoblasts in a concentration-dependent manner. Icariside I increases the cytotoxicity of adriamycin in multidrug-resistant MCF-7/adr breast cancer cells with an IC50 value of 60.78 µM.


Chemical Structure

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Icariside I
CAS# 56725-99-6

Theoretical Analysis

MedKoo Cat#: 463979
Name: Icariside I
CAS#: 56725-99-6
Chemical Formula: C27H30O11
Exact Mass: 530.1788
Molecular Weight: 530.526
Elemental Analysis: C, 61.13; H, 5.70; O, 33.17

Price and Availability

Size Price Availability Quantity
1.0mg USD 230.0 2 Weeks
5.0mg USD 500.0 2 Weeks
10.0mg USD 830.0 2 Weeks
25.0mg USD 1440.0 2 Weeks
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Synonym: Icariside I; Icariside-I;

IUPAC/Chemical Name: 3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

InChi Key: IYCPMVXIUPYNHI-WPKKLUCLSA-N

InChi Code: InChI=1S/C27H30O11/c1-12(2)4-9-15-17(36-27-24(34)22(32)20(30)18(11-28)37-27)10-16(29)19-21(31)23(33)25(38-26(15)19)13-5-7-14(35-3)8-6-13/h4-8,10,18,20,22,24,27-30,32-34H,9,11H2,1-3H3/t18-,20-,22+,24-,27-/m1/s1

SMILES Code: C/C(C)=C\CC1=C2C(C(C(O)=C(O2)C3=CC=C(OC)C=C3)=O)=C(O)C=C1O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

Appearance: 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

Preparing Stock Solutions

The following data is based on the product molecular weight 530.526 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.

Recalculate based on batch purity %
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

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1: Wang M, Gao H, Li W, Wu B. Icariin and its metabolites regulate lipid metabolism: From effects to molecular mechanisms. Biomed Pharmacother. 2020 Nov;131:110675. doi: 10.1016/j.biopha.2020.110675. Epub 2020 Aug 28. PMID: 32861069.

2: Tang XY, Dai ZQ, Wu QC, Zeng JX, Gao MX, Xiao HH, Yao ZH, Dai Y, Yao XS. Simultaneous determination of multiple components in rat plasma and pharmacokinetic studies at a pharmacodynamic dose of Xian-Ling-Gu-Bao capsule by UPLC-MS/MS. J Pharm Biomed Anal. 2020 Jan 5;177:112836. doi: 10.1016/j.jpba.2019.112836. Epub 2019 Aug 26. PMID: 31473481.

3: Teo YL, Cheong WF, Cazenave-Gassiot A, Ji S, Logan S, Lee ZXK, Li J, Seng KY, Lee LS, Yong EL. Pharmacokinetics of Prenylflavonoids following Oral Ingestion of Standardized Epimedium Extract in Humans. Planta Med. 2019 Mar;85(4):347-355. doi: 10.1055/a-0806-7673. Epub 2018 Dec 6. PMID: 30522143.

4: Liu M, Xu H, Ma Y, Cheng J, Hua Z, Huang G. Osteoblasts Proliferation and Differentiation Stimulating Activities of the Main Components of Epimedii folium. Pharmacogn Mag. 2017 Jan-Mar;13(49):90-94. doi: 10.4103/0973-1296.197654. PMID: 28216889; PMCID: PMC5307921.

5: Cheng T, Sheng T, Yi Y, Zhang T, Han H. Metabolism profiles of icariin in rats using ultra-high performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry and in vitro enzymatic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Oct 15;1033-1034:353-360. doi: 10.1016/j.jchromb.2016.09.010. PMID: 27620672.

6: Wu H, Kim M, Han J. Icariin Metabolism by Human Intestinal Microflora. Molecules. 2016 Aug 31;21(9):1158. doi: 10.3390/molecules21091158. PMID: 27589718; PMCID: PMC6273050.

7: Sun E, Xu F, Qian Q, Cui L, Tan X, Jia X. Metabolite Profiles of Icariin in Rat Feces, Bile and Urine by Ultraperformance Liquid-Chromatography/Quadrupole- Time-of-Flight Mass Spectrometry. J Chromatogr Sci. 2016 Feb;54(2):158-64. doi: 10.1093/chromsci/bmv121. PMID: 26792083.

8: Ming LG, Chen KM, Xian CJ. Functions and action mechanisms of flavonoids genistein and icariin in regulating bone remodeling. J Cell Physiol. 2013 Mar;228(3):513-21. doi: 10.1002/jcp.24158. PMID: 22777826.

9: Qian Q, Li SL, Sun E, Zhang KR, Tan XB, Wei YJ, Fan HW, Cui L, Jia XB. Metabolite profiles of icariin in rat plasma by ultra-fast liquid chromatography coupled to triple-quadrupole/time-of-flight mass spectrometry. J Pharm Biomed Anal. 2012 Jul;66:392-8. doi: 10.1016/j.jpba.2012.03.053. Epub 2012 Apr 5. PMID: 22522037.

10: Wong SP, Shen P, Lee L, Li J, Yong EL. Pharmacokinetics of prenylflavonoids and correlations with the dynamics of estrogen action in sera following ingestion of a standardized Epimedium extract. J Pharm Biomed Anal. 2009 Sep 8;50(2):216-23. doi: 10.1016/j.jpba.2009.04.022. Epub 2009 May 3. PMID: 19464838.

11: Shen P, Wong SP, Li J, Yong EL. Simple and sensitive liquid chromatography- tandem mass spectrometry assay for simultaneous measurement of five Epimedium prenylflavonoids in rat sera. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jan 1;877(1-2):71-8. doi: 10.1016/j.jchromb.2008.11.030. Epub 2008 Nov 27. PMID: 19083275.

12: Qin L, Han T, Zhang Q, Cao D, Nian H, Rahman K, Zheng H. Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula. J Ethnopharmacol. 2008 Jul 23;118(2):271-9. doi: 10.1016/j.jep.2008.04.009. Epub 2008 Apr 15. PMID: 18501540.

13: Park JS, Park HY, Rho HS, Ahn S, Kim DH, Chang IS. Statistically designed enzymatic hydrolysis for optimized production of icariside II as a novel melanogenesis inhibitor. J Microbiol Biotechnol. 2008 Jan;18(1):110-7. PMID: 18239426.

14: Huang H, Liang M, Zhang X, Zhang C, Shen Z, Zhang W. Simultaneous determination of nine flavonoids and qualitative evaluation of Herba Epimedii by high performance liquid chromatography with ultraviolet detection. J Sep Sci. 2007 Dec;30(18):3207-13. doi: 10.1002/jssc.200700262. PMID: 18008281.

15: Xu W, Zhang Y, Yang M, Shen Z, Zhang X, Zhang W, Li H. LC-MS/MS method for the simultaneous determination of icariin and its major metabolites in rat plasma. J Pharm Biomed Anal. 2007 Nov 30;45(4):667-72. doi: 10.1016/j.jpba.2007.07.007. Epub 2007 Jul 10. PMID: 17706393.

16: Liang HR, Yan WM, Li L, Jiang L, Dai L. [Studies on the chemical constituents of Epimedium acuminatum Franch]. Zhongguo Zhong Yao Za Zhi. 1993 Nov;18(11):677-9, 703. Chinese. PMID: 8003229.