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| CAS No.: | 42017-89-0 |
|---|---|
| Name: | Fenofibric acid |
| Article Data: | 25 |
| Molecular Structure: | |
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|
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| 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 |
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- 49562-28-9
fenofibrate
- 42017-89-0
fenofibric acid
| 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 | 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 | 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.; |
| 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 |
- 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 | Yield |
|---|---|
| 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 | 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 | 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 | 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 | 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% |
| 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% |
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History
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
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. |