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Basic Information

Molecular Structure:
CAS No.:	25812-30-0
Name:	Gemfibrozil
Article Data:	19

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

Synthetic route

: 169295-45-8
2,2-dimethyl-5-(2,5-dimethylphenoxy)-3-hydroxypentanoic acid β-lactone

: 25812-30-0
gemfibrozil

Conditions

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

Conditions	Yield
With sodium hydroxide In diethyl ether; ethanol; water	82%

: methyl 5-(2,5-dimethylphenoxy)-2,2-dimethyl-pentanoate

: 25812-30-0
gemfibrozil

Conditions

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

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

: 201230-82-2
carbon monoxide

: 5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

: 25812-30-0
gemfibrozil

Conditions

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

Conditions	Yield
With copper(I) oxide; sulfuric acid at -12 - -8℃;	47%

: 201230-82-2
carbon monoxide

: 5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

A: 25812-30-0
gemfibrozil

B: 2,2-dimethyl-5-(2,5-dimethyl-4-sulfophenoxy)pentanoic acid

Conditions

Conditions	Yield
With copper(I) oxide; sulfuric acid at 0 - 5℃; for 4h;	A n/a B 2.0 g

...Expand

: 201230-82-2
carbon monoxide

: 172533-96-9
2-methyl-5-(2,5-dimethylphenoxy)-2-pentene

A: 25812-30-0
gemfibrozil

B: 2,2-dimethyl-5-(2,5-dimethyl-4-formylphenoxy)pentanoic acid

Conditions

Conditions	Yield
With sulfuric acid at -16℃; for 24h;	A 3.5 g B 1.5 g

...Expand

: 5-(2,5-dimethylphenoxy)-2-methylpentan-2-ol

: 25812-30-0
gemfibrozil

Conditions

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

1-p-xylyl-4-methyl-1.2.3-triazole: 1-p-xylyl-4-methyl-1.2.3-triazole

: 25812-30-0
gemfibrozil

Conditions

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

Raw Materials

71-36-3

95-87-4

Total:194 Page 1 of 6 1 2 3 4 5 6 Next>>

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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

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: Harmful

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.

Production of Gemfibrozil