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| CAS No.: | 25812-30-0 |
|---|---|
| Name: | Gemfibrozil |
| Article Data: | 19 |
| Molecular Structure: | |
|
|
|
| Formula: | C15H22O3 |
| Molecular Weight: | 250.338 |
| Synonyms: | 2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeure;Lipira;Normolip;2,2-Dimethyl-5-(2,5-xylyloxy)valeric acid;Valeric acid, 2,2-dimethyl-5-(2,5-xylyloxy)-;WL-Gemfibrozil;Gozid;Litarek;Gemfibrozilum [INN-Latin];Pentanoic acid,5-(2,5-dimethylphenoxy)-2,2- dimethyl-;Apo-Gemfibrozil;Lipazil;Regulip;Lanaterom;Gemfibromax;Low-Lip;Gevilon Uno;Gemfibrozil [USAN:BAN:INN];Decrelip;Taborcil;Micolip;CI 719;Lifibron;Sinelip;Ipolipid;Reducel;2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeure;Gemfibrozil (JAN/USP);CI-719;Fibratol;Jezil;Brozil;Gemfibrozilo [INN-Spanish];Hipolixan;Gemd;Pilder;Gem-S;Lipur;5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid;Fibrocit;Lopid;Pentanoic acid, 5-(2,5-dimethylphenoxy)-2,2-dimethyl-;Ausgem;Gemnpid;Clearol; |
| EINECS: | 247-280-2 |
| Density: | 1.044 g/cm3 |
| Melting Point: | 61-63 °C |
| Boiling Point: | 394.7 °C at 760 mmHg |
| Flash Point: | 141.6 °C |
| Solubility: | >0.5g/L(temperature not stated) |
| Appearance: | White crystalline powder |
| Hazard Symbols: |
 Xn,  Xi
|
| Risk Codes: | 22-63-62-46-36/38-21 |
| Safety: | 36-53-36/37-26-25 |
| PSA: | 46.53000 |
| LogP: | 3.57320 |
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- 169295-45-8
2,2-dimethyl-5-(2,5-dimethylphenoxy)-3-hydroxypentanoic acid β-lactone
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate In N,N-dimethyl-formamide for 12h; Ambient temperature; | 90% |
- 139483-63-9
1,3-Bis[2.2-dimethyl-5-(2,5-dimethylphenoxy)-pentanoyloxy]-propane
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| With sodium hydroxide In diethyl ether; ethanol; water | 82% |
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| With tetrabutylammomium bromide; water; sodium hydroxide at 73 - 75℃; for 3h; Inert atmosphere; | 77.6% |
| With sodium hydroxide In dimethyl sulfoxide; toluene for 4h; | 860 mg |
- 39938-97-1
5-(2,5-dimethylphenoxy)-2,2-dimethylpentanal
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; under 760.051 Torr; for 10h; Schlenk technique; | 72% |
| With potassium carbonate In n-heptane; water |
| Conditions | Yield |
|---|---|
| With copper(I) oxide; sulfuric acid at -12 - -8℃; for 1.5h; | 56% |
- 201230-82-2
carbon monoxide
- 172533-96-9
2-methyl-5-(2,5-dimethylphenoxy)-2-pentene
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| With copper(I) oxide; sulfuric acid at -12 - -8℃; | 47% |
- 201230-82-2
carbon monoxide
A
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| With copper(I) oxide; sulfuric acid at 0 - 5℃; for 4h; | A n/a B 2.0 g |
- 201230-82-2
carbon monoxide
- 172533-96-9
2-methyl-5-(2,5-dimethylphenoxy)-2-pentene
A
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| With sulfuric acid at -16℃; for 24h; | A 3.5 g B 1.5 g |
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 66.9 percent / potassium bisulfite / 1.) from 50 to 60 deg C, 5 Torr, 5 min, 2.) from 60 to 120 deg C, 20 min 2: 47 percent / 1.) 98percent H2SO4, Cu2O / -12 - -8 °C View Scheme | |
| Multi-step reaction with 2 steps 1: 66.9 percent / potassium bisulfite / 1.) from 50 to 60 deg C, 5 Torr, 5 min, 2.) from 60 to 120 deg C, 20 min 2: 3.5 g / 98percent H2SO4 / 24 h / -16 °C View Scheme |
- 95-87-4
2,5-Dimethylphenol
- 25812-30-0
gemfibrozil
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 91 percent / aq. NaOH, tetrabutylammonium hydroxide / 24 h / Heating 2: 90 percent / aq. p-TsOH / ethyl acetate / 60 °C 3: 90 percent / ZnCl2 / ethyl acetate / 30 h / 4 °C 4: 90 percent / NaBH4 / dimethylformamide / 12 h / Ambient temperature View Scheme | |
| Multi-step reaction with 4 steps 1: 90 percent / aq. NaOH, tetrabutylammonium hydroxide / Heating 2: aq. p-TsOH / ethyl acetate / 0.75 h / 60 °C 3: 90 percent / ZnCl2 / ethyl acetate / 30 h / 4 °C 4: 90 percent / NaBH4 / dimethylformamide / 12 h / Ambient temperature View Scheme |
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Specification
1. Introduction of Gemfibrozil
Gemfibrozil is one kind of white or off-white crystalline powder. The IUPAC Name of this chemical is 5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid. It belongs to Active Pharmaceutical Ingredients;APIs;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Intracellular receptor.
The Classification Code of Gemfibrozil is Antihyperlipidemic; Antilipemic agents; Antimetabolites; Drug / Therapeutic Agent; Human Data; Hypolipidemic Agents; Lipid Regulating Agents; Reproductive Effect; Tumor data.
2. Properties of Gemfibrozil
Physical properties about Gemfibrozil are:
(1)Melting point: 61-63 °C; (2)Index of Refraction: 1.511; (3)Density: 1.044 g/cm3; (4)Flash Point: 141.6 °C; (5)Enthalpy of Vaporization: 68 kJ/mol; (6)Boiling Point: 394.7 °C at 760 mmHg; (7)Vapour Pressure: 6.13E-07 mmHg at 25 °C; (8)Appearance: White crystalline powder; (9)XLogP3-AA: 3.8; (10)H-Bond Donor: 1; (11)H-Bond Acceptor: 3.
3. Structure Descriptors of Gemfibrozil
(1)InChI: InChI=1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)
(2)InChIKey: InChIKey=HEMJJKBWTPKOJG-UHFFFAOYSA-N
(3)Smiles: c1(c(ccc(c1)C)C)OCCCC(C(O)=O)(C)C
4. Toxicity of Gemfibrozil
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LDLo | oral | 2gm/kg (2000mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25, Pg. 699, 1997. |
| man | TDLo | oral | 18gm/kg/3Y-I (18000mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Archives of Internal Medicine. Vol. 151, Pg. 1873, 1991. |
| mouse | LD50 | oral | 2218mg/kg (2218mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Toksikologicheskii Vestnik. Vol. (6), Pg. 38, 1995. |
| rat | LD50 | intraperitoneal | 445mg/kg (445mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Toksikologicheskii Vestnik. Vol. (6), Pg. 38, 1995. |
| rat | LD50 | oral | 1414mg/kg (1414mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25, Pg. 645, 1997. |
5. Physical Properties of Gemfibrozil
| Physical Property | Value | Units | Temp (deg C) | Source |
|---|---|---|---|---|
| Melting Point | 62 | deg C | EXP | |
| log P (octanol-water) | 4.770 | (none) | EST | |
| Atmospheric OH Rate Constant | 8.24E-11 | cm3/molecule-sec | 25 | EST |
Or
| 1. | orl-rat LD50:4786 mg/kg | PRSMA4 Proceedings of the Royal Society of Medicine. 69 (Suppl 2)(1976),15. | ||
| 2. | orl-mus LD50:3162 mg/kg | PRSMA4 Proceedings of the Royal Society of Medicine. 69 (Suppl 2)(1976),15. |
6. Safety information of Gemfibrozil
Hazard Codes:
Xn,
Xi Risk Statements: 22-63-62-46-36/38-21
R21:Harmful in contact with skin.
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
R46:May cause heritable genetic damage.
R62:Risk of impaired fertility.
R63:Possible risk of harm to the unborn child.
Safety Statements: 36-53-36/37-26-25
S25:Avoid contact with eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S36/37:Wear suitable protective clothing and gloves.
S53:Avoid exposure - obtain special instructions before use.
7. Uses of Gemfibrozil
Gemfibrozil (CAS NO.25812-30-0) is a serum lipid regulating agent used as an antihyperlipoproteinemic. It is a serum lipid regulating agent used as an antihyperlipoproteinemic. Gemfibrozil helps reduce cholesterol and triglycerides (fatty acids) in the blood. High levels of these types of fat in the blood are associated with an increased risk of atherosclerosis (clogged arteries).
8. Production of Gemfibrozil
(1)2,5-Dimethylphenol and 1-Bromo-3-chloropropane reaction of 1-(2,5-dimethylphenoxy)-3-chloropropane. The reaction is carried out in toluene, adding new clean off reflux 5h. Just as follows:
(2)N/A can be used to manufacture Gemfibrozil.
