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191282-48-1,MFCD03265452
Catalog No.:AA002F2J

191282-48-1 | C75 trans

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1mg
≥98%
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$63.00   $44.00
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5mg
≥98%
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$169.00   $118.00
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10mg
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$246.00   $172.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002F2J
Chemical Name:
C75 trans
CAS Number:
191282-48-1
Molecular Formula:
C14H22O4
Molecular Weight:
254.3221
MDL Number:
MFCD03265452
SMILES:
CCCCCCCC[C@H]1OC(=O)C(=C)[C@@H]1C(=O)O
Properties
Properties
 
BP:
432.1?°C at 760 mmHg  
Form:
Solid  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
322  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
8  
XLogP3:
4  

Downstream Synthesis Route
CASUnavailable 
  191282-48-1 

[1]Chakrabarty,Kuheli;Forzato,Cristina;Nitti,Patrizia;Pitacco,Giuliana;Valentin,Ennio[LettersinOrganicChemistry,2010,vol.7,#3,p.245-248]

[1]Chakrabarty,Kuheli;Defrenza,Ivana;Denora,Nunzio;Drioli,Sara;Forzato,Cristina;Franco,Massimo;Lentini,Giovanni;Nitti,Patrizia;Pitacco,Giuliana[Chirality,2015,vol.27,#3,p.239-246]

CASUnavailable 
  191282-48-1    1800594-49-3 

[1]Chakrabarty,Kuheli;Defrenza,Ivana;Denora,Nunzio;Drioli,Sara;Forzato,Cristina;Franco,Massimo;Lentini,Giovanni;Nitti,Patrizia;Pitacco,Giuliana[Chirality,2015,vol.27,#3,p.239-246]

[2]Chakrabarty,Kuheli;Defrenza,Ivana;Denora,Nunzio;Drioli,Sara;Forzato,Cristina;Franco,Massimo;Lentini,Giovanni;Nitti,Patrizia;Pitacco,Giuliana[Chirality,2015,vol.27,#3,p.239-246]

CASUnavailable 
  191282-48-1    1800594-49-3 

[1]Chakrabarty,Kuheli;Defrenza,Ivana;Denora,Nunzio;Drioli,Sara;Forzato,Cristina;Franco,Massimo;Lentini,Giovanni;Nitti,Patrizia;Pitacco,Giuliana[Chirality,2015,vol.27,#3,p.239-246]

[2]Chakrabarty,Kuheli;Defrenza,Ivana;Denora,Nunzio;Drioli,Sara;Forzato,Cristina;Franco,Massimo;Lentini,Giovanni;Nitti,Patrizia;Pitacco,Giuliana[Chirality,2015,vol.27,#3,p.239-246]

[1]Makowski,Kamil;Mir,JoanFrancesc;Mera,Paula;Ariza,Xavier;Asins,Guillermina;Hegardt,FaustoG.;Herrero,Laura;García,Jordi;Serra,Dolors[EuropeanJournalofMedicinalChemistry,2017,vol.131,p.207-221]

Literature

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Journal: Molecular cancer 20150101

Title: U18666A, an intra-cellular cholesterol transport inhibitor, inhibits dengue virus entry and replication.

Journal: Antiviral research 20120101

Title: The effects of C75, an inhibitor of fatty acid synthase, on sleep and metabolism in mice.

Journal: PloS one 20120101

Title: Blockade of fatty acid synthase induces ubiquitination and degradation of phosphoinositide-3-kinase signaling proteins in ovarian cancer.

Journal: Molecular cancer research : MCR 20111201

Title: Fatty acid synthase expression in Barrett's esophagus: implications for carcinogenesis.

Journal: Journal of clinical gastroenterology 20110901

Title: The lipogenesis pathway as a cancer target.

Journal: Journal of medicinal chemistry 20110825

Title: Carnitine palmitoyltransferase (CPT) modulators: a medicinal chemistry perspective on 35 years of research.

Journal: Journal of medicinal chemistry 20110512

Title: Overexpression of fatty acid synthase in Middle Eastern epithelial ovarian carcinoma activates AKT and Its inhibition potentiates cisplatin-induced apoptosis.

Journal: Molecular medicine (Cambridge, Mass.) 20110101

Title: Inhibition of fatty acid synthase suppresses c-Met receptor kinase and induces apoptosis in diffuse large B-cell lymphoma.

Journal: Molecular cancer therapeutics 20100501

Title: Fatty acid synthase phosphorylation: a novel therapeutic target in HER2-overexpressing breast cancer cells.

Journal: Breast cancer research : BCR 20100101

Title: Fatty acid oxidation and meiotic resumption in mouse oocytes.

Journal: Molecular reproduction and development 20090901

Title: Interaction between fatty acid synthase- and ErbB-systems in ovarian cancer cells.

Journal: Biochemical and biophysical research communications 20090731

Title: C75 is converted to C75-CoA in the hypothalamus, where it inhibits carnitine palmitoyltransferase 1 and decreases food intake and body weight.

Journal: Biochemical pharmacology 20090315

Title: Novel fatty acid synthase (FAS) inhibitors: design, synthesis, biological evaluation, and molecular docking studies.

Journal: Bioorganic & medicinal chemistry 20090301

Title: Fatty acid synthase inhibitor, C75, blocks resistin-induced increases in lipid accumulation by human macrophages.

Journal: Diabetes, obesity & metabolism 20081201

Title: Effect of centrally administered C75, a fatty acid synthase inhibitor, on gastric emptying and gastrointestinal transit in mice.

Journal: European journal of pharmacology 20081024

Title: Fatty acid synthase and AKT pathway signaling in a subset of papillary thyroid cancers.

Journal: The Journal of clinical endocrinology and metabolism 20081001

Title: Intraperitoneal injections of low doses of C75 elicit a behaviorally specific and vagal afferent-independent inhibition of eating in rats.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20080901

Title: Fatty acid metabolism in breast cancer cells: differential inhibitory effects of epigallocatechin gallate (EGCG) and C75.

Journal: Breast cancer research and treatment 20080601

Title: Inhibiting fatty acid synthase for chemoprevention of chemically induced lung tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080415

Title: Examining the relationship between Cu-ATSM hypoxia selectivity and fatty acid synthase expression in human prostate cancer cell lines.

Journal: Nuclear medicine and biology 20080401

Title: An easy, rapid and objective mathematical method to identify fatty acid synthase (oncogenic antigen-519) modulators with potential anticancer value.

Journal: Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico 20080401

Title: Lipid bodies are reservoirs of cyclooxygenase-2 and sites of prostaglandin-E2 synthesis in colon cancer cells.

Journal: Cancer research 20080315

Title: Molecular docking study of the interactions between the thioesterase domain of human fatty acid synthase and its ligands.

Journal: Proteins 20080301

Title: Pharmacological stimulation of brain carnitine palmitoyl-transferase-1 decreases food intake and body weight.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20080201

Title: Physiological glucose is critical for optimized neuronal viability and AMPK responsiveness in vitro.

Journal: Journal of neuroscience methods 20080130

Title: Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism.

Journal: Nature chemical biology 20080101

Title: The human fatty acid synthase: a new therapeutic target for coxsackievirus B3-induced diseases?

Journal: Antiviral research 20071101

Title: Pharmacological blockade of fatty acid synthase (FASN) reverses acquired autoresistance to trastuzumab (Herceptin by transcriptionally inhibiting 'HER2 super-expression' occurring in high-dose trastuzumab-conditioned SKBR3/Tzb100 breast cancer cells.

Journal: International journal of oncology 20071001

Title: Fatty acid synthase inhibitors cerulenin and C75 retard growth and induce caspase-dependent apoptosis in human melanoma A-375 cells.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20071001

Title: FDG-PET for pharmacodynamic assessment of the fatty acid synthase inhibitor C75 in an experimental model of lung cancer.

Journal: Pharmaceutical research 20070601

Title: The GCN2 eIF2alpha kinase regulates fatty-acid homeostasis in the liver during deprivation of an essential amino acid.

Journal: Cell metabolism 20070201

Title: Inhibition of fatty acid synthase induces endoplasmic reticulum stress in tumor cells.

Journal: Cancer research 20070201

Title: DNA topoisomerase IIalpha (TOP2A) inhibitors up-regulate fatty acid synthase gene expression in SK-Br3 breast cancer cells: in vitro evidence for a 'functional amplicon' involving FAS, Her-2/neu and TOP2A genes.

Journal: International journal of molecular medicine 20061201

Title: Growth arrest induced by C75, A fatty acid synthase inhibitor, was partially modulated by p38 MAPK but not by p53 in human hepatocellular carcinoma.

Journal: Cancer biology & therapy 20060801

Title: Cancer therapy: back to metabolism.

Journal: Cancer biology & therapy 20060801

Title: Fatty acid metabolism, the central nervous system, and feeding.

Journal: Obesity (Silver Spring, Md.) 20060801

Title: Intracerebroventricular C75 decreases meal frequency and reduces AgRP gene expression in rats.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20060701

Title: Novel effect of C75 on carnitine palmitoyltransferase I activity and palmitate oxidation.

Journal: Biochemistry 20060411

Title: The connections between C75 and obesity drug-target pathways.

Journal: Trends in pharmacological sciences 20051101

Title: Characterization of the inactivation of rat fatty acid synthase by C75: inhibition of partial reactions and protection by substrates.

Journal: The Biochemical journal 20050615

Title: Pharmacological inhibition of AMP-activated protein kinase provides neuroprotection in stroke.

Journal: The Journal of biological chemistry 20050527

Title: Positive feedback regulation between AKT activation and fatty acid synthase expression in ovarian carcinoma cells.

Journal: Oncogene 20050519

Title: Fatty acid metabolism as a target for obesity treatment.

Journal: Physiology & behavior 20050519

Title: Inhibition of fatty acid synthase prevents preadipocyte differentiation.

Journal: Biochemical and biophysical research communications 20050325

Title: Disconnection between the early onset anorectic effects by C75 and hypothalamic fatty acid synthase inhibition in rodents.

Journal: European journal of pharmacology 20050321

Title: Fatty acid synthase inhibitors are chemopreventive for mammary cancer in neu-N transgenic mice.

Journal: Oncogene 20050106

Title: C75 [4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid] activates carnitine palmitoyltransferase-1 in isolated mitochondria and intact cells without displacement of bound malonyl CoA.

Journal: The Journal of pharmacology and experimental therapeutics 20050101

Title: C75 alters central and peripheral gene expression to reduce food intake and increase energy expenditure.

Journal: Endocrinology 20050101

Title: C75 activates malonyl-CoA sensitive and insensitive components of the CPT system.

Journal: Biochemical and biophysical research communications 20041217

Title: Effects of a fatty acid synthase inhibitor on adipocyte differentiation of mouse 3T3-L1 cells.

Journal: Acta pharmacologica Sinica 20040801

Title: Chronic C75 treatment of diet-induced obese mice increases fat oxidation and reduces food intake to reduce adipose mass.

Journal: American journal of physiology. Endocrinology and metabolism 20040701

Title: C75, a fatty acid synthase inhibitor, reduces food intake via hypothalamic AMP-activated protein kinase.

Journal: The Journal of biological chemistry 20040507

Title: Long-term effects of a fatty acid synthase inhibitor on obese mice: food intake, hypothalamic neuropeptides, and UCP3.

Journal: Biochemical and biophysical research communications 20040430

Title: Anorexigenic C75 alters c-Fos in mouse hypothalamic and hindbrain subnuclei.

Journal: Neuroreport 20040409

Title: C75, a fatty acid synthase inhibitor, modulates AMP-activated protein kinase to alter neuronal energy metabolism.

Journal: The Journal of biological chemistry 20040130

Title: The anorexigenic fatty acid synthase inhibitor, C75, is a nonspecific neuronal activator.

Journal: Endocrinology 20040101

Title: Fatty acid synthase inhibition triggers apoptosis during S phase in human cancer cells.

Journal: Cancer research 20031101

Title: Effect of the anorectic fatty acid synthase inhibitor C75 on neuronal activity in the hypothalamus and brainstem.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20030513

Title: C75 inhibits food intake by increasing CNS glucose metabolism.

Journal: Nature medicine 20030501

Title: Expression of FAS within hypothalamic neurons: a model for decreased food intake after C75 treatment.

Journal: American journal of physiology. Endocrinology and metabolism 20021101

Title: Comparison of central and peripheral administration of C75 on food intake, body weight, and conditioned taste aversion.

Journal: Diabetes 20021101

Title: Block the FAS, lose the fat.

Journal: Nature medicine 20020401

Title: Thin mice and fat mice respond differently to appetite suppressant.

Journal: Lancet (London, England) 20020223

Title: Green tea epigallocatechin gallate: a natural inhibitor of fatty-acid synthase.

Journal: Biochemical and biophysical research communications 20011116

Title: Increased fatty acid synthase as a therapeutic target in androgen-independent prostate cancer progression.

Journal: The Prostate 20010501

Title: Increased fatty acid synthase is a therapeutic target in mesothelioma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20010101

Title: Rae C, et al. Inhibition of Fatty Acid Synthase Sensitizes Prostate Cancer Cells to Radiotherapy.

Title: Makowski K, et al. Differential pharmacologic properties of the two C75 enantiomers: (+)-C75 is a strong anorectic drug; (-)-C75 has antitumor activity. Chirality. 2013 May;25(5):281-7.

Title: Gao S, et al. Effect of the anorectic fatty acid synthase inhibitor C75 on neuronal activity in the hypothalamus and brainstem. Proc Natl Acad Sci U S A. 2003 May 13;100(10):5628-33.

Title: Thupari JN, et al. C75 increases peripheral energy utilization and fatty acid oxidation in diet-induced obesity. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9498-502.

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SDS
Tags:191282-48-1 Molecular Formula|191282-48-1 MDL|191282-48-1 SMILES|191282-48-1 C75 trans