191282-48-1 Usage
Chemical Description
C75 is another compound whose in vitro FAS inhibitory activity is being studied.
Description
Trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid, also known as trans-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylic Acid, is a compound with significant biological activities. It is a well-known inhibitor of fatty acid synthase (FAS), an enzyme involved in the synthesis of fatty acids. trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid has been found to have potential applications in various fields due to its ability to modulate cellular processes and inhibit specific enzymes.
Uses
Used in Pharmaceutical Industry:
Trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid is used as a pharmaceutical agent for its potential role in the treatment of various diseases. Its ability to inhibit fatty acid synthase (FAS) makes it a promising candidate for the development of drugs targeting metabolic disorders and cancer.
Used in Cancer Research:
In cancer research, trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid is used as a cell cycle arrest inducer in hepatocellular carcinoma (HCC) cell lines. This property suggests its potential use in the development of targeted therapies for liver cancer.
Used in Metabolic Disorder Research:
Trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid is used as a research tool to study the role of fatty acid synthase (FAS) in metabolic disorders. By inhibiting FAS, this compound can help researchers understand the underlying mechanisms of these disorders and develop novel therapeutic strategies.
Used in Obesity and Lipid Metabolism Research:
Trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid has been shown to block resistin-induced increases in lipid accumulation by human macrophages. This finding indicates its potential use in the development of treatments for obesity and related metabolic complications.
Biological Activity
c 75 is an inhibitor of fatty acid synthase [1].fatty acid synthase (fas) is a multi-enzyme protein that catalyzes fatty acid synthesis. its main function is to catalyze the synthesis of palmitate from acetyl-coa and malonyl-coa. fas is a target for anticancer drug [1].in human breast cancer cells, c 75 reacted preferentially with fas and inhibited fas. the antitumor activity of c 75 is likely mediated by its inhibition of fas [1]. in primary cortical neurons, c 75 inhibited fas activity and increased the activity of carnitine palmitoyltransferase-1 (cpt-1) and fatty acid oxidation, which suggested that c 75 might influence cellular energy balance through regulation of these metabolic pathways. also, c 75 altered neuronal atp levels in a biphasic manner (decreasing initially, followed by a prolonged increase above control levels). the amp-activated protein kinase (ampk) activity was also influenced by c 75 [2]. in human melanoma a-375 cells, c 75 inhibited cell growth through activation of caspase-dependent apoptosis [3].in diet induced obese (dio) mice, chronic c 75 treatment reduced food intake and increased energy expenditure due to increased fatty acid oxidation. c 75 significantly reduced adipose tissue. the reduced food intake was accompanied by an increase in amphetamine and cocaine-related transcript expression [4].
references
[1]. kuhajda fp, pizer es, li jn, et al. synthesis and antitumor activity of an inhibitor of fatty acid synthase. proc natl acad sci u s a, 2000, 97(7): 3450-3454.[2]. landree le, hanlon al, strong dw, et al. c75, a fatty acid synthase inhibitor, modulates amp-activated protein kinase to alter neuronal energy metabolism. j biol chem, 2004, 279(5): 3817-3827.[3]. ho ts, ho yp, wong wy, et al. fatty acid synthase inhibitors cerulenin and c75 retard growth and induce caspase-dependent apoptosis in human melanoma a-375 cells. biomed pharmacother, 2007, 61(9): 578-587.[4]. thupari jn, kim ek, moran th, et al. chronic c75 treatment of diet-induced obese mice increases fat oxidation and reduces food intake to reduce adipose mass. am j physiol endocrinol metab, 2004, 287(1): e97-e104.
Check Digit Verification of cas no
The CAS Registry Mumber 191282-48-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,1,2,8 and 2 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 191282-48:
(8*1)+(7*9)+(6*1)+(5*2)+(4*8)+(3*2)+(2*4)+(1*8)=141
141 % 10 = 1
So 191282-48-1 is a valid CAS Registry Number.
InChI:InChI=1/C14H22O4/c1-3-4-5-6-7-8-9-11-12(13(15)16)10(2)14(17)18-11/h11-12H,2-9H2,1H3,(H,15,16)/t11-,12+/m1/s1
191282-48-1Relevant articles and documents
Total syntheses of paraconic acids and 1,10-seco-guaianolides via a barbier allylation/translactonization cascade of 3-(Bromomethyl)-2(5H)-furanone
Liu, Weilong,Yu, Zhimei,Winssinger, Nicolas
, p. 969 - 973 (2021/03/03)
A palladium-catalyzed Barbier allylation/translactonization cascade reaction was established for the rapid construction of β,γdisubstituted α-exo-methylene-γ-butyrolactone, an important motif in sesquiterpenes. Dimethyl zinc played significant roles in bo
The first kinetic enzymatic resolution of methyl ester of C75
Chakrabarty, Kuheli,Forzato, Cristina,Nitti, Patrizia,Pitacco, Giuliana,Valentin, Ennio
, p. 245 - 248 (2011/06/28)
Enantioselective hydrolysis of methyl ester of (±)-C75 was successfully accomplished by means of Acylase I from Aspergillus to afford (2,R,3S)-(+)-C75 with 96% e.e. The unreacted methyl ester was recovered with >99% e.e. This latter compound was either chemically or enzymatically hydrolyzed to furnish (2S,3,R)-(-)-C75 with >99% e.e.
