Clinofibrate

Last updated
Clinofibrate
Clinofibrate.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 2-(4-{1-[4-(1-carboxy-1-methylpropoxy)phenyl]cyclohexyl}phenoxy)-2-methylbutanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C28H36O6
Molar mass 468.590 g·mol−1
3D model (JSmol)
  • CCC(C)(C(=O)O)OC1=CC=C(C=C1)C2(CCCCC2)C3=CC=C(C=C3)OC(C)(CC)C(=O)O
  • InChI=1S/C28H36O6/c1-5-26(3,24(29)30)33-22-15-13-20(14-16-22)28(17-8-7-9-18-28)21-11-10-12-23(19-21)34-27(4,6-2)25(31)32/h10-16,19H,5-9,17-18H2,1-4H3,(H,29,30)(H,31,32) X mark.svgN
  • Key:OGGAHXJZRRGBTK-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Clinofibrate (INN) (trade name Lipoclin) is a fibrate and a derivative of Bisphenol Z. [1]

Synthesis

Clinofibrate synthesis.svg

The reaction between cyclohexanone and phenol gives Bisphenol Z (3). [2] This is treated with chloroform and methyl ethyl ketone in the presence of base. The resulting Bargellini reaction gives clinofibrate. [3]

Related Research Articles

In calculus, the chain rule is a formula that expresses the derivative of the composition of two differentiable functions f and g in terms of the derivatives of f and g. More precisely, if is the function such that for every x, then the chain rule is, in Lagrange's notation, or, equivalently,

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Polycarbonate</span> Family of polymers

Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, tough materials, and some grades are optically transparent. They are easily worked, molded, and thermoformed. Because of these properties, polycarbonates find many applications. Polycarbonates do not have a unique resin identification code (RIC) and are identified as "Other", 7 on the RIC list. Products made from polycarbonate can contain the precursor monomer bisphenol A (BPA).

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.

<span class="mw-page-title-main">Bisphenol A</span> Chemical compound used in plastics manufacturing

Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes.

In organic chemistry, the Hammett equation describes a linear free-energy relationship relating reaction rates and equilibrium constants for many reactions involving benzoic acid derivatives with meta- and para-substituents to each other with just two parameters: a substituent constant and a reaction constant. This equation was developed and published by Louis Plack Hammett in 1937 as a follow-up to qualitative observations in his 1935 publication.

<span class="mw-page-title-main">Cefmenoxime</span> Chemical compound

Cefmenoxime is a third-generation cephalosporin antibiotic.

<span class="mw-page-title-main">Fullerene chemistry</span>

Fullerene chemistry is a field of organic chemistry devoted to the chemical properties of fullerenes. Research in this field is driven by the need to functionalize fullerenes and tune their properties. For example, fullerene is notoriously insoluble and adding a suitable group can enhance solubility. By adding a polymerizable group, a fullerene polymer can be obtained. Functionalized fullerenes are divided into two classes: exohedral fullerenes with substituents outside the cage and endohedral fullerenes with trapped molecules inside the cage.

The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxyacids to give the corresponding α-hydroxy carbonyl product. The mechanism of the reaction was proposed in its original disclosure by A.G. Brook with further evidence later supplied by George M. Rubottom. After a Prilezhaev-type oxidation of the silyl enol ether with the peroxyacid to form the siloxy oxirane intermediate, acid-catalyzed ring-opening yields an oxocarbenium ion. This intermediate then participates in a 1,4-silyl migration to give an α-siloxy carbonyl derivative that can be readily converted to the α-hydroxy carbonyl compound in the presence of acid, base, or a fluoride source.

The Kulinkovich reaction describes the organic synthesis of substituted cyclopropanols through reaction of esters with dialkyl­dialkoxy­titanium reagents, which are generated in situ from Grignard reagents containing a hydrogen in beta-position and titanium(IV) alkoxides such as titanium isopropoxide. This reaction was first reported by Oleg Kulinkovich and coworkers in 1989.

<span class="mw-page-title-main">Tetrabromobisphenol A</span> Chemical compound

Tetrabromobisphenol A (TBBPA) is a brominated flame retardant. The compound is a white solid, although commercial samples appear yellow. It is one of the most common flame retardants.

The bisphenols are a group of industrial chemical compounds related to diphenylmethane; commonly used in the creation of plastics and epoxy resins. Most are based on two hydroxyphenyl functional groups linked by a methylene bridge. Exceptions include bisphenol S, P, and M. "Bisphenol" is a common name; the letter following denotes the variant, which depends on the additional substituents. Bisphenol A is the most popular representative of the group, with millions of metric tons produced globally in the past decade, often simply called "bisphenol".

<span class="mw-page-title-main">Pinacolone</span> Chemical compound

Pinacolone (3,3-dimethyl-2-butanone) is an important ketone in organic chemistry. It is a colorless liquid and has a slight peppermint- or camphor- odor. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. The molecule is an unsymmetrical ketone. The α-methyl group can participate in condensation reactions. The carbonyl group can undergo the usual reactions. It is a Schedule 3 compound under the Chemical Weapons Convention 1993, due to being related to pinacolyl alcohol, which is used in the production of soman. It is also a controlled export in Australia Group member states.

<span class="mw-page-title-main">Estrogen-related receptor gamma</span> Protein-coding gene in the species Homo sapiens

Estrogen-related receptor gamma (ERR-gamma), also known as NR3B3, is a nuclear receptor that in humans is encoded by the ESRRG gene. It behaves as a constitutive activator of transcription.

<span class="mw-page-title-main">Bisphenol S</span> Chemical compound

Bisphenol S (BPS) is an organic compound with the formula (HOC6H4)2SO2. It has two phenol functional groups on either side of a sulfonyl group. It is commonly used in curing fast-drying epoxy resin adhesives. It is classified as a bisphenol, and a close molecular analog of bisphenol A (BPA). BPS differentiates from BPA by possessing a sulfone group (SO2) as the central linker of the molecule instead of a dimethylmethylene group (C 2), which is the case of bisphenol A.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

<span class="mw-page-title-main">Xylylene</span>

In organic chemistry, a xylylene (sometimes quinone-dimethide) is any of the constitutional isomers having the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene are best known, although neither is stable in solid or liquid form. The meta form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, such as tetracyanoquinodimethane and the xylylene dichlorides.

<span class="mw-page-title-main">4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene</span> Chemical compound

4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene (MBP) is a metabolite of bisphenol A (BPA). MBP has potent estrogenic activity in vitro and in vivo, up to thousandfold stronger than BPA. It may also play a role in neuronal cell apoptosis and may increase risk for several forms of cancer.

In organic chemistry, the hexadehydro-Diels–Alder (HDDA) reaction is an organic chemical reaction between a diyne and an alkyne to form a reactive benzyne species, via a [4+2] cycloaddition reaction. This benzyne intermediate then reacts with a suitable trapping agent to form a substituted aromatic product. This reaction is a derivative of the established Diels–Alder reaction and proceeds via a similar [4+2] cycloaddition mechanism. The HDDA reaction is particularly effective for forming heavily functionalized aromatic systems and multiple ring systems in one synthetic step.

<span class="mw-page-title-main">Bisphenol Z</span> Chemical compound

Bisphenol Z is an organic compound with the formula (HOC6H4)2C(CH2)5. This white, water-insoluble solid is classified as a bisphenol. It is a precursor to specialty polycarbonate plastics. It is prepared by the condensation on phenol and cyclohexanone:

References

  1. Takeuchi N, Kukita H, Kajiyama G, Fujiyama M, Ishikawa K, Miki H, Mishima T, Murata K, Asano T (April 1982). "Effect of clinofibrate, a new hypolipidemic agent, on biliary and serum lipids in patients with hyperlipidemia". Atherosclerosis. 42 (2–3): 129–39. doi:10.1016/0021-9150(82)90145-9. PMID   7073798.
  2. Patil LS, Suryawanshi VS, Pawar OB, Shinde ND (2011). "An Improved, Highly Efficient Method for the Synthesis of Bisphenols". e-Journal of Chemistry. 8 (4): 2016–2019. doi: 10.1155/2011/372673 .
  3. US 3716583,Nakamura Y, Aono S, Agatsuma K, Tanaka Y,"Phenoxy carboxylic acid derivative",issued 13 February 1973, assigned to Sumitomo Chemical Company