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42017-89-0

Basic Information
CAS No.: 42017-89-0
Name: Fenofibric acid
Molecular Structure:
Molecular Structure of 42017-89-0 (Fenofibric acid)
Formula: C17H15ClO4
Molecular Weight: 318.75
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
Solubility:
Appearance: white to off-white solid
Hazard Symbols:
Risk Codes: 36/37/38
Safety: 26-36/37/39
Transport Information:
PSA: 63.60000
LogP: 3.81300
Synthetic route
49562-28-9

fenofibrate

42017-89-0

fenofibric acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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
ConditionsYield
With cesiumhydroxide monohydrate; sodium carbonate; sodium iodide; Trimethylacetic acid In ethylene glycol at 120℃; for 48h; Sealed tube; Green chemistry;72%
42019-08-9

2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid ethyl ester

42017-89-0

fenofibric acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
42017-89-0

fenofibric acid

1-Phenylethynyl-1H-1λ3-benzo[d][1,2]iodoxol-3-one

(4-chlorophenyl)(4-((2-methyl-4-phenylbut-3-yn-2-yl)oxy)phenyl)methanone

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 25℃; for 16h; Catalytic behavior; Irradiation; Inert atmosphere; Sealed tube;97%
847682-00-2

1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

42017-89-0

fenofibric acid

1043468-87-6

1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;96%
42017-89-0

fenofibric acid

75-26-3

isopropyl bromide

49562-28-9

fenofibrate

Conditions
ConditionsYield
Stage #1: fenofibric acid With potassium carbonate In Isopropyl acetate; dimethyl sulfoxide at 20 - 90℃; for 0.75h; Industry scale; Inert atmosphere;
Stage #2: isopropyl bromide In Isopropyl acetate; dimethyl sulfoxide at 80 - 95℃; for 5.83333h;
94.9%
42017-89-0

fenofibric acid

72577-81-2

2-(4-((4-chlorophenyl)(hydroxy)methyl)phenoxy)-2-methylpropan-1-ol

Conditions
ConditionsYield
Stage #1: fenofibric acid With borane-THF In tetrahydrofuran at 0 - 50℃; for 3h; Inert atmosphere;
Stage #2: With methanol In tetrahydrofuran at 0℃;
94%
With borane-THF In tetrahydrofuran at 0 - 50℃; for 3h; Inert atmosphere;94%
42017-89-0

fenofibric acid

C16H14(2)HClO2

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; 2,4,6-Triisopropylthiophenol; water-d2; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane for 16h; Irradiation;94%
42017-89-0

fenofibric acid

80841-78-7

4-chloromethyl-5-methyl-1,3-dioxol-2-one

1319719-25-9

(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl-2‑(4‑(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 65℃;93%
With sodium carbonate In N,N-dimethyl acetamide at 30℃; for 17h; Inert atmosphere;83%
42017-89-0

fenofibric acid

C6H11ClO2

(2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoyloxy) methylpivalate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 65℃;93%
42017-89-0

fenofibric acid

54419-30-6

2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanamide

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran at 20℃; for 1h;93%
42017-89-0

fenofibric acid

30379-58-9

benzyl glycolate

2-(benzyloxy)-2-oxoethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;92.31%
42017-89-0

fenofibric acid

65178-90-7

2-[4-(4-chlorobenzoyl)-phenoxy]-2-methylpropionyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h;91.4%
With thionyl chloride In Petroleum ether; benzene83.2%
With thionyl chloride In benzene Heating;
42017-89-0

fenofibric acid

71630-31-4, 7738-22-9

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

852056-04-3

C29H36ClNO8

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h;87%
42017-89-0

fenofibric acid

ethyl (R)-2-((mesitylsulfinyl)imino)acetate

C29H32ClNO5S

Conditions
ConditionsYield
With 9-mesityl-2,7-dimethyl-10-phenylacridin-10-ium tetrafluoroborate; potassium carbonate at 20℃; Inert atmosphere; Irradiation; diastereoselective reaction;87%
524-38-9

N-hydroxyphthalimide

42017-89-0

fenofibric acid

1,3-dioxoisoindolin-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;86%
In dichloromethane
42017-89-0

fenofibric acid

53064-79-2

iodomethyl pivaloate

42019-36-3

2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid pivaloyloxymethyl ester

Conditions
ConditionsYield
Stage #1: fenofibric acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -5℃; for 0.333333h; Inert atmosphere;
Stage #2: iodomethyl pivaloate In N,N-dimethyl acetamide at -5℃; for 0.25h; Inert atmosphere;
85%
42017-89-0

fenofibric acid

84089-73-6, 91508-00-8

1-iodoethyl isopropyl carbonate

1319719-22-6

2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid 1-isopropoxy carbonyloxyethyl ester

Conditions
ConditionsYield
Stage #1: fenofibric acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -5℃; for 0.333333h; Inert atmosphere;
Stage #2: 1-iodoethyl isopropyl carbonate In N,N-dimethyl acetamide at -5℃; for 0.75h; Inert atmosphere;
85%
542-58-5

2-chloro-1-acetoxyethane

42017-89-0

fenofibric acid

2-acetoxyethyl-2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 65℃;85%
109-83-1

(2-hydroxyethyl)(methyl)amine

42017-89-0

fenofibric acid

2-[4-(4-chlorobenzoyl)phenoxy]-N-(2-hydroxyethyl)-N,2-dimethylpropanamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;85%
258841-42-8

isopropyloxycarbonyloxymethyl iodide

42017-89-0

fenofibric acid

1319719-24-8

2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid isopropoxycarbonyl oxymethyl ester

Conditions
ConditionsYield
Stage #1: fenofibric acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: isopropyloxycarbonyloxymethyl iodide In N,N-dimethyl acetamide at 0℃; for 0.5h; Inert atmosphere;
83%
42017-89-0

fenofibric acid

140-88-5

ethyl acrylate

C22H21ClO6

Conditions
ConditionsYield
With tert-Amyl alcohol; t-Boc-L-valine; oxygen; palladium diacetate; potassium hydrogencarbonate at 90℃; for 24h; Schlenk technique;83%
42017-89-0

fenofibric acid

30588-71-7

N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester

852056-05-4

C30H38ClNO8

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 96h;82%
42017-89-0

fenofibric acid

613-89-8

2-Aminoacetophenone

2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl-N-(2-oxo-2-phenylethyl)propanamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;82%
89774-36-7

morpholine-4-carboxylic acid 2-chloro-ethyl ester

42017-89-0

fenofibric acid

(2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoyloxy)ethylmorpholine-4-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 65℃;82%
42017-89-0

fenofibric acid

berberine hemisulfate salt

berberine salt of fenofibric acid

Conditions
ConditionsYield
With sodium hydroxide In water82%
42017-89-0

fenofibric acid

633-65-8

berberine chloride

berberine salt of fenofibric acid

Conditions
ConditionsYield
Stage #1: fenofibric acid With sodium hydroxide In water
Stage #2: berberine chloride In water Solvent; Temperature; Heating;
82%
3240-94-6

N-(2-chlorethyl)morpholine

42017-89-0

fenofibric acid

2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid 2-(morpholin-4-yl)ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 65℃;81%
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    Name:Fenofibric acid Synonyms : 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid; 2-[4'-(p-Chlorobenzoyl)phenoxy]-2-methylpropionic acid Molecular Formula : C17H15ClO4 Molecular Weight : 318.76 CAS:42017-89-0 Appearance:White powde

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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.