709-55-7

Usage

Therapeutic Function

Tranquilizer

InChI:InChI=1S/C10H15NO2/c1-2-11-7-10(13)8-4-3-5-9(12)6-8/h3-6,10-13H,2,7H2,1H3

Upstream product

• 22510-12-9 2-ethylamino-1-(3-hydroxy-phenyl)-ethanone 
• 536-21-0 norfenefrine 
• 75-07-0 acetaldehyde 
• 425-75-2 trifluoromethanesulfonic acid ethyl ester 
• 620-18-8 3-hydroxystyrene 
• 100-83-4 meta-hydroxybenzaldehyde 
• 1415155-47-3 3-(non-8-enyl)phenol 
• 38396-89-3 2-bromo-3-acetyloxylacetophenone 

Downstream Products

• 81104-39-4 3-hydroxyphenylacetaldehyde 
• 132034-26-5 C-((S)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-N-ethyl-N-[2-hydroxy-2-(3-hydroxy-phenyl)-ethyl]-methanesulfonamide 
• 2259-99-6 (R)-N-ethylnorphenylephrine 
• 95585-90-3 (S)-etilefrine 

Relevant academic research and scientific papers

Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid

Cardanol from cashew nut shell liquid extracted from cashew nut shells was successfully converted into various useful pharmaceutical drugs, such as norfenefrine, rac-phenylephrine, etilefrine and fenoprofene. 3-Vinylphenol, the key intermediate for the synthesis of these drugs, was synthesised from cardanol by ethenolysis to 3-non-8-enylphenol followed by isomerising ethenolysis. The metathesis reaction worked very well using DCM, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. Hydroxyamination of 3-vinylphenol with an iron porphyrin catalyst afforded norfenefrine in over 70% yield. Methylation and ethylation of norfenefrine afforded rac-phenylephrine and etilefrine respectively. A sequence of C-O coupling, isomerising metathesis and selective methoxycarbonylation afforded fenoprofene in good yield. A comparison of the routes described in this paper with some standard literature syntheses of 3-vinylphenol and of the drug molecules shows significant environmental advantages in terms of precursors, yields, number of steps, conditions and the use of catalysts. The Atom Economy of our processes is generally similar or significantly superior to those of the literature processes mainly because the side products produced during synthesis of 3-vinylphenol (1-octeme, 1,4-cyclohexadiene and propene) are easily separable and of commercial value, especially as they are bio-derived. The E Factor for the production of 2-vinylphenol by our process is also very low compared with those of previously reported syntheses.

Pharmaceutical formula

The present invention concerns a pharmacological vehicle or carrier system, which makes possible administration of the active ingredient with a high absorption thereof in the blood circulation of the patient treated therewith, in particular also in the case of oral administration. The pharmacological vehicle system according to the invention comprises ultrafine particles of a reaction product of a reactive derivative of an at least dibasic inorganic acid or an alkane-carboxylic acid having 2 or 3 carboxyl groups and optionally one or two hydroxy groups, wherein one bond of the dibasic inorganic acid or one carboxy group of the alkane-carboxylic acid is bonded to a pharmacological active ingredient containing a hydroxy group, SH group and/or a primary or secondary amino group having a ractive hydrogen atom on this group, and the other bond is bonded to the free hydroxy group of a glycerolipid having at least one free hydroxy group on the glycerol. The invention further concerns these reaction products and a process for the preparation of ultrafine particles of these reaction products.