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Basic Information

Molecular Structure:
CAS No.:	42017-89-0
Name:	Fenofibric acid
Article Data:	25

Formula:	C₁₇H₁₅ClO₄
Molecular Weight:	318.757
Synonyms:	2-[4'-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid;2-[p-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid;FNF acid;LF 153;LF 178 acid;NSC 281318;Procetofenic acid;a-1081;2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoic acid;Propanoic acid,2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-;
EINECS:	255-626-9
Density:	1.287 g/cm³
Melting Point:	177-179 °C
Boiling Point:	486.457 °C at 760 mmHg
Flash Point:	248.001 °C
Appearance:	white to off-white solid
Hazard Symbols:	2058973
Risk Codes:	36/37/38
Safety:	26-36/37/39
PSA:	63.60000
LogP:	3.81300

Synthetic route

: 49562-28-9
fenofibrate

: 42017-89-0
fenofibric acid

Conditions

Conditions	Yield
With water; triethylamine; lithium bromide In acetonitrile for 7h; Heating;	99%
With iodine; aluminium In acetonitrile at 80℃; for 18h;	97%
With sodium hydroxide In methanol at 69.85℃; for 4h;	85%

: 1159999-13-9
benzyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate

: 42017-89-0
fenofibric acid

Conditions

Conditions	Yield
Stage #1: benzyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate With potassium hydroxide In ethanol for 16h; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1;	91%

: 2052-01-9
2-bromo-2-methylpropionic acid

: 42019-78-3
4-chloro-4'-hydroxybenzophenone

: 42017-89-0
fenofibric acid

Conditions

Conditions	Yield
Stage #1: 4-chloro-4'-hydroxybenzophenone With sodium hydroxide In butanone at 50℃; for 1h; Stage #2: 2-bromo-2-methylpropionic acid In butanone at 50℃; for 16h;	87%
Multistep reaction.;

: 67-66-3
chloroform

: 42019-78-3
4-chloro-4'-hydroxybenzophenone

: 67-64-1
acetone

: 42017-89-0
fenofibric acid

Conditions

Conditions	Yield
Stage #1: 4-chloro-4'-hydroxybenzophenone; acetone With sodium hydroxide for 2h; Heating / reflux; Stage #2: chloroform In acetone for 8h; Heating / reflux;	73%
With sodium hydroxide
With sodium hydroxide

...Expand

: 67-66-3
chloroform

: 37404-23-2
2-(4-iodophenoxy)-2-methylpropanoic acid

: 1679-18-1
4-Chlorophenylboronic acid

: 42017-89-0
fenofibric acid

Conditions

Conditions	Yield
With cesiumhydroxide monohydrate; sodium carbonate; sodium iodide; Trimethylacetic acid In ethylene glycol at 120℃; for 48h; Sealed tube; Green chemistry;	72%

...Expand

: 42019-08-9
2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid ethyl ester

: 42017-89-0
fenofibric acid

Conditions

Conditions	Yield
With water; sodium hydroxide In ethanol at 25℃; Temperature;	0.95 g

: 122-01-0
4-chloro-benzoyl chloride

: 42017-89-0
fenofibric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminium trichloride 2: sodium hydroxide View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / toluene / 1.5 h / 0 °C / Inert atmosphere; Reflux 2.1: sodium hydroxide / butanone / 1 h / Reflux 2.2: 8 h / Reflux 3.1: sodium hydroxide / 4 h / Reflux View Scheme

: 100-66-3
methoxybenzene

: 42017-89-0
fenofibric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminium trichloride 2: sodium hydroxide View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / toluene / 1.5 h / 0 °C / Inert atmosphere; Reflux 2.1: sodium hydroxide / butanone / 1 h / Reflux 2.2: 8 h / Reflux 3.1: sodium hydroxide / 4 h / Reflux View Scheme

: 49715-04-0
chlorosulfuric acid chloromethyl ester

: 42017-89-0
fenofibric acid

: 1094101-30-0
chloromethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Conditions

Conditions	Yield
Stage #1: fenofibric acid With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In water at 20℃; for 0.25h; Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃; Cooling with ice;	100%

: 42017-89-0
fenofibric acid

: 67-63-0
isopropyl alcohol

: 49562-28-9
fenofibrate

Conditions

Conditions	Yield
With magneticnanosolidsuperacid In cyclohexane; water at 83 - 85℃; Reagent/catalyst; Temperature;	97%
Stage #1: fenofibric acid; isopropyl alcohol With thionyl chloride for 7h; Reflux; Stage #2: With potassium carbonate In water at 60 - 65℃;	96.6%
With macroporous strong acid cation exchange resin D001 In water; toluene at 110℃;	92.4%

Raw Materials

42019-78-3

67-64-1

122-01-0

67-66-3

100-66-3

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History

From the Department of Biochemistry, Cell Biology, and Metabolism (R.A., S.Y.), Nagoya City University Graduate School of Medical Sciences, Japan; Research and Development Institute (R.A.), Grelan Pharmaceutical Co., Tokyo, Japan; Division of Biosignaling (N.T., T.N.-M.), National Institute of Health Sciences, Tokyo, Japan; and Division of Applied Life Sciences (K.U.), Graduate School of Agriculture, Kyoto University, Japan.

Consensus Reports

Fenofibric acid increased transcription of ABCA1 gene in a liver X receptor–dependent manner. Fibrates are widely used drugs to reduce plasma triglyceride and increase high-density lipoprotein. Their active forms, fibric acids, are peroxisome proliferator-activated receptor- activators, but no direct evidence has been demonstrated for their activation of ATP-binding cassette transporter A1 (ABCA1) in relation to clinically used fibrates. We investigated the reaction of fenofibric acid in this regard, finding that fenofibric acid increased transcription of ABCA1 gene in n liver X receptor–dependent manner.

Analytical Methods

Fenofibric acid was examined for the effect of increase of ABCA1 activity. It enhanced ABCA1 gene transcription and its protein level in macrophage cell line cells and fibroblasts and increased apolipoprotein A-I–mediated cellular lipid release, all in a dose-dependent manner. Enhancement of the gene transcription was examined by using a reporter assay system for liver X receptor responsive element (LXRE) and its inactive mutant. The results demonstrated that the effect of fenofibric acid is dependent on active LXRE.

Specification

The Fenofibric acid belongs to the product categories of Pharmacetical; Various Metabolites and Impurities; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; Aromatics. Its EINECS number is 255-626-9. What's more, its systematic name is 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid. Its classification codes are: (1)Anticholesteremic Agents; (2)Antilipemic agents; (3)Antimetabolites; (4)Drug / Therapeutic Agent. This chemical is used as pharmaceutical intermediates and intermediate of fenofibrate. It is the active metabolite of fenofibrate.

Physical properties of Fenofibric acid are:
(1)ACD/LogP: 3.992; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.60; (4)ACD/LogD (pH 7.4): 0.35; (5)ACD/BCF (pH 5.5): 2.55; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 14.17; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 63.6 Å²; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 83.048 cm³; (15)Molar Volume: 247.696 cm³; (16)Polarizability: 32.923×10^-24cm³; (17)Surface Tension: 49.10 dyne/cm; (18)Density: 1.287 g/cm³; (19)Flash Point: 248.001 °C; (20)Enthalpy of Vaporization: 79.223 kJ/mol; (21)Boiling Point: 486.457 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Safety Information of Fenofibric acid:
When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection.

You could convert the following datas into the molecular structure:
(1)SMILES: O=C(c1ccc(Cl)cc1)c2ccc(OC(C(=O)O)(C)C)cc2
(2)Std. InChI: InChI=1S/C17H15ClO4/c1-17(2,16(20)21)22-14-9-5-12(6-10-14)15(19)11-3-7-13(18)8-4-11/h3-10H,1-2H3,(H,20,21)
(3)Std. InChIKey: MQOBSOSZFYZQOK-UHFFFAOYSA-N

Toxicity of Fenofibric acid are as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	500mg/kg (500mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 885, 1976.
mouse	LD50	oral	1200mg/kg (1200mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 885, 1976.
rat	LD50	intravenous	313mg/kg (313mg/kg)	LUNGS, THORAX, OR RESPIRATION: PLEURAL THICKENING BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 23.
rat	LD50	oral	1242mg/kg (1242mg/kg)		Drugs of the Future. Vol. 7, Pg. 229, 1982.