Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Preparation of 3,7-Bis(2-hydroxyethyl)icaritin
mr4563f2
Harmless
*




Posts: 1
Registered: 28-7-2009
Member Is Offline

Mood: No Mood

[*] posted on 28-7-2009 at 21:43
Preparation of 3,7-Bis(2-hydroxyethyl)icaritin


i would like make this preparation at home using chemicals that are available to the general public : Preparation of 3,7-Bis(2-hydroxyethyl)icaritin Potent Inhibition of Human Phosphodiesterase-5 by Icariin Derivatives
A stirred suspension of icariin 95% (250 mg, 0.7 mmol), 2-bromoethanol (210 mg, 1.7 mmol), and anhydrous K2CO3 (240 mg, 1.7 mmol) in dry acetone (75 mL) was refluxed for 8 h. The hot reaction mixture was filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (CH2Cl2/acetone, 9:1) and crystallized from EtOH to give the desired compound as a yellow crystalline powder (70 mg, purity 96.0%); 20.2% yield; mp 152−153 °C; 1H NMR (CDCl3, 300 MHz, 30 °C) δ 1.77 (3H, s, CH3-14), 1.87 (3H, s, CH3-15), 3.61 (2H, d, J = 6.8 Hz, H-11), 3.78−3.83 (2H, m, 7-OCH2O), 3.90 (3H, s, OCH3), 3.95−4.05 (4H, m, CH2OH), 4.15−4.22 (2H, m, OCH2O-3), 5.19 (1H, t, J = 6.8 Hz, H-12), 6.32 (1H, s, H-6), 7.04 (2H, d, J = 8.4 Hz, H-3′, H-5′;), 8.16 (2H, d, J = 8.4 Hz, H-2′, H-6′;); ESIMS (positive-ion mode) m/z 479 [M + Na]+; anal. C 65.82%, H 6.22%, calcd for C25H28O8, C 65.78%, H 6.18%.

[Edited on 29-7-2009 by mr4563f2]

[Edited on 29-7-2009 by mr4563f2]

[Edited on 29-7-2009 by mr4563f2]
View user's profile View All Posts By User
JohnWW
International Hazard
*****




Posts: 2849
Registered: 27-7-2004
Location: New Zealand
Member Is Offline

Mood: No Mood

[*] posted on 28-7-2009 at 22:07


What is the reference from which that preparation, and NMR and MS spectra, are extracted? An icaritin derivative? - that sounds as if it might be of use as a mosquito repellant.

P.S. Sorry; - I confused Icaridin (or Picaridin), which is used as a mosquito repellant, see:
http://en.wikipedia.org/wiki/Icaridin ,
http://www.who.int/whopes/quality/en/Icaridin_spec_eval_Oct_...
http://www.mosquitozone.com/education/Preview/assets/MZ_Post...
http://www.alanwood.net/pesticides/icaridin.html
http://wikirank.com/en/Icaridin
http://en.allexperts.com/e/i/ic/icaridin.htm
http://www.docstoc.com/docs/612187/WHO-ICARIDIN-Evaluation

with Icaritin and its derivatives which (with Icariin) are used as an anti-cancer chemotherapy drug, and for other purposes e.g. to prevent osteonecrosis, see:
http://www.faqs.org/patents/app/20080214844 and http://www.curehunter.com/public/keywordSummaryC499403-icari...
http://www.mitochondrial.net/showabstract.php?pmid=17382317
http://www.journals.elsevierhealth.com/periodicals/bon/artic...
http://www.nature.com/aps/journal/v26/n4/abs/aps200572a.html
http://www.labmeeting.com/paper/28653503/zhang-2009-a-novel-...
http://sciencestage.com/d/69441/a-novel-semisynthesized-smal...
http://www.find-health-articles.com/rec_pub_17632044-sensiti...
http://cat.inist.fr/?aModele=afficheN&cpsidt=21126265
http://www.ingentaconnect.com/content/bsc/aphs/2005/00000026...

[Edited on 29-7-09 by JohnWW]
View user's profile View All Posts By User
Bolt
Hazard to Others
***




Posts: 188
Registered: 26-3-2007
Member Is Offline

Mood: No Mood

[*] posted on 28-7-2009 at 23:32


It's actually supposed to enhance the stingers
View user's profile View All Posts By User
stoichiometric_steve
National Hazard
****




Posts: 827
Registered: 14-12-2005
Member Is Offline

Mood: satyric

[*] posted on 29-7-2009 at 11:19


Quote: Originally posted by mr4563f2  
Potent Inhibition of Human Phosphodiesterase-5 by Icariin Derivatives


Viagra.




View user's profile View All Posts By User
UnintentionalChaos
International Hazard
*****




Posts: 1454
Registered: 9-12-2006
Location: Mars
Member Is Offline

Mood: Nucleophilic

[*] posted on 29-7-2009 at 11:46


http://www.nationalpost.com/related/topics/story.html?id=845...

If I'm understanding this right, it simply has 2-hydroxyethyl groups replacing the two sugars on the natural molecule.

[Edited on 7-29-09 by UnintentionalChaos]




Department of Redundancy Department - Now with paperwork!

'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
View user's profile View All Posts By User
Arrhenius
Hazard to Others
***




Posts: 282
Registered: 17-8-2008
Location: US & A
Member Is Offline

Mood: Stochastic

[*] posted on 29-7-2009 at 23:42


I highly doubt this will work. The NMR is fishy, as 25 protons is inconsistent with the mass and formula given, and the mass is inconsistent with possible resultant structures. I would not be surprised if this method alkylates the phenol and does nothing to the two hexoses.
View user's profile View All Posts By User

  Go To Top