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MedKoo Cat#: 581380 | Name: Desmethyl icaritin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Desmethyl Icaritin is a metabolite of Icariin that inhibits the growth of most malignant cells. Desmethyl Icaritin has significant antiangiogenesis properties.

Chemical Structure

Desmethyl icaritin
Desmethyl icaritin
CAS# 28610-31-3

Theoretical Analysis

MedKoo Cat#: 581380

Name: Desmethyl icaritin

CAS#: 28610-31-3

Chemical Formula: C20H18O6

Exact Mass: 354.1103

Molecular Weight: 354.36

Elemental Analysis: C, 67.79; H, 5.12; O, 27.09

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Synonym
8-Prenylkaempferol; Desmethyl Icaritin; Noranhydroicaritin; Desmethylicaritin; 4'-Desmethylicaritin; De-O-methylanhydroicaritin; Noranhydroicartin; 8-c-prenylkaempferol;
IUPAC/Chemical Name
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
InChi Key
NADCVNHITZNGJU-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H18O6/c1-10(2)3-8-13-14(22)9-15(23)16-17(24)18(25)19(26-20(13)16)11-4-6-12(21)7-5-11/h3-7,9,21-23,25H,8H2,1-2H3
SMILES Code
O=C1C(O)=C(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O)=C3C/C=C(C)\C
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 354.36 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
1: Wu H, Kim M, Han J. Icariin Metabolism by Human Intestinal Microflora. Molecules. 2016 Aug 31;21(9). pii: E1158. doi: 10.3390/molecules21091158. PubMed PMID: 27589718. 2: Indran IR, Zhang SJ, Zhang ZW, Sun F, Gong Y, Wang X, Li J, Erdelmeier CA, Koch E, Yong EL. Selective estrogen receptor modulator effects of epimedium extracts on breast cancer and uterine growth in nude mice. Planta Med. 2014 Jan;80(1):22-8. doi: 10.1055/s-0033-1360112. Epub 2013 Dec 5. PubMed PMID: 24310211. 3: Wang XL, Wang N, Zheng LZ, Xie XH, Yao D, Liu MY, Yao ZH, Dai Y, Zhang G, Yao XS, Qin L. Phytoestrogenic molecule desmethylicaritin suppressed adipogenesis via Wnt/β-catenin signaling pathway. Eur J Pharmacol. 2013 Aug 15;714(1-3):254-60. doi: 10.1016/j.ejphar.2013.06.008. Epub 2013 Jun 20. PubMed PMID: 23792141. 4: 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. Review. PubMed PMID: 22777826. 5: 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. PubMed PMID: 22522037. 6: Li HF, Guan XY, Ye M, Xiang C, Lin CH, Sun C, Guo DA. Qualitative and quantitative analyses of Epimedium wushanense by high-performance liquid chromatography coupled with diode array detection and electrospray ionization tandem mass spectrometry. J Sep Sci. 2011 Jun;34(12):1437-46. doi: 10.1002/jssc.201000899. Epub 2011 May 10. PubMed PMID: 21560245. 7: 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. PubMed PMID: 19464838. 8: 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. PubMed PMID: 19083275. 9: Wo YB, Zhu DY, Hu Y, Wang ZQ, Liu J, Lou YJ. Reactive oxygen species involved in prenylflavonoids, icariin and icaritin, initiating cardiac differentiation of mouse embryonic stem cells. J Cell Biochem. 2008 Apr 1;103(5):1536-50. PubMed PMID: 17985362. 10: Shen P, Wong SP, Yong EL. Sensitive and rapid method to quantify icaritin and desmethylicaritin in human serum using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Sep 15;857(1):47-52. Epub 2007 Jul 1. PubMed PMID: 17632044. 11: Ye HY, Lou YJ. Estrogenic effects of two derivatives of icariin on human breast cancer MCF-7 cells. Phytomedicine. 2005 Nov;12(10):735-41. PubMed PMID: 16323292. 12: Ye HY, Liu J, Lou YJ. [Preparation of two derivatives from icariin and investigation of their estrogen-like effects]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2005 Mar;34(2):131-6. Chinese. PubMed PMID: 15812886. 13: Zhu DY, Lou YJ. Inducible effects of icariin, icaritin, and desmethylicaritin on directional differentiation of embryonic stem cells into cardiomyocytes in vitro. Acta Pharmacol Sin. 2005 Apr;26(4):477-85. PubMed PMID: 15780198. 14: Liu J, Ye H, Lou Y. Determination of rat urinary metabolites of icariin in vivo and estrogenic activities of its metabolites on MCF-7 cells. Pharmazie. 2005 Feb;60(2):120-5. PubMed PMID: 15739900. 15: Wang ZQ, Lou YJ. Proliferation-stimulating effects of icaritin and desmethylicaritin in MCF-7 cells. Eur J Pharmacol. 2004 Nov 19;504(3):147-53. PubMed PMID: 15541416. 16: Liu J, Lou YJ. Determination of icariin and metabolites in rat serum by capillary zone electrophoresis: rat pharmacokinetic studies after administration of icariin. J Pharm Biomed Anal. 2004 Oct 29;36(2):365-70. PubMed PMID: 15496330.

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