Fenipentol

Structural formula
	Structural formula without stereochemistry
General
Non-proprietary name	Fenipentol
other names	( RS ) -1-phenylpentan-1-ol ( IUPAC ); (±) -1-phenyl-1-hydroxy- n -pentane; ( RS ) -phenylbutylcarbinol; (±) -α-Butylbenzyl alcohol;
Molecular formula	C 11 H 16 O
Brief description	colorless to slightly yellowish liquid
External identifiers / databases
EC number	209-493-9
ECHA InfoCard	100.008.632
PubChem	3338
Wikidata	Q426345
Drug information
ATC code	A05 AX07
Drug class	Choleretic
properties
Molar mass	164.24 g · mol -1
density	0.9655 g cm −3 (20 ° C )
solubility	miscible with organic liquids, practically immiscible with water
Refractive index	1.4086 (25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 319-400
	P: 273-305 + 351 + 338
Toxicological data	2900 mg kg −1 ( LD 50 , mouse , oral ) ; 5432 mg kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Fenipentol is a drug that stimulates bile secretion and therefore belongs to the group of choleretics . The drug has a stereocenter, so it is chiral and is present as a racemate [1: 1 mixture of the ( R ) isomer and the ( S ) isomer].

It was synthetically derived from a gall-active ingredient in the turmeric plant ( Curcuma domestica ), p -Tolylmethylcarbinol [according to IUPAC : 1- (4-methylphenyl) ethanol]. Its toxicity is lower than that of the parent compound.

Structure of p -tolylmethylcarbinol

synthesis

One possible synthetic route starts from styrene epoxide . In the presence of sodium ethoxide, styrene epoxide reacts with acetoacetic ester to form α-acetyl-γ-phenyl-γ-butyrolactone, which further reacts to 5-hydroxy-5-phenyl-pentanone by heating in ethanolic hydrochloric acid , splitting off carbon dioxide . Fenipentol is produced in a Wolff-Kishner reaction by refluxing with hydrazine and potassium hydroxide .

Another synthetic route is the reaction of benzaldehyde with n -butylmagnesium bromide, the Grignard compound made of n -butylbromide and magnesium, and subsequent hydrolysis .

Trade names

Febichol (D, except trade)

literature

Hermann J. Roth et al. Helmut Fenner: Drugs . Thieme, Stuttgart a. New York 1988. pp. 598-599.

Individual evidence

^ ^A ^b The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 679, ISBN 978-0-911910-00-1 .
↑ ^a ^b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-430.
↑ ^a ^b Data sheet 1-PHENYL-1-PENTANOL from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).
^ ^A ^b ^c A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .
^ Siegfried Ebel: Hagers Handbook of Pharmaceutical Practice. Springer, 1999, ISBN 978-3-540-62644-2 , p. 500 ( limited preview in Google book search).

[MERCK_Index-1] A ^b The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 679, ISBN 978-0-911910-00-1 .

[CRC90_3_430-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-430.

[Sigma-3] Data sheet 1-PHENYL-1-PENTANOL from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).

[Kleemann-4] A ^b ^c A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .

[5] Siegfried Ebel: Hagers Handbook of Pharmaceutical Practice. Springer, 1999, ISBN 978-3-540-62644-2 , p. 500 ( limited preview in Google book search).