C75 trans [(±)-C75] is an isomer/enantiomer of C75 which is a synthetic fatty-acid synthase (FASN) inhibitor. It has weight loss and feeding inhibition in both high-fat diet wild type obese and leptin-deficient ob/ob mice.
Physicochemical Properties
| Molecular Formula | C₁₄H₂₂O₄ |
| Molecular Weight | 254.32 |
| Exact Mass | 254.151 |
| CAS # | 191282-48-1 |
| Related CAS # | C75;218137-86-1;(−)-C75;1234694-22-4 |
| PubChem CID | 9881506 |
| Appearance | White to off-white solid powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 432.1±45.0 °C at 760 mmHg |
| Flash Point | 159.2±22.2 °C |
| Vapour Pressure | 0.0±2.2 mmHg at 25°C |
| Index of Refraction | 1.489 |
| LogP | 3.65 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 18 |
| Complexity | 322 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CCCCCCCC[C@@H]1[C@H](C(=C)C(=O)O1)C(=O)O |
| InChi Key | CWLZDVWHQVAJU-JHJMLUEUSA-N |
| InChi Code | InChI=1S/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 |
| Chemical Name | tetrahydro-4-methylene-2R-octyl-5-oxo-3S-furancarboxylic acid |
| Synonyms | (±)-C75 C75 C75 FASN inhibitor |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | trans-C75 ((±)-C75) inhibits PC3 cell growth with an IC50 of 35 μM at 24 hours. trans-C75 ((±)-C75) (10-50 μM) still decreases the development of LNCaP spheres at concentrated concentrations trans-C75 ((±)-C75) is active in inhibiting FAS and has cytotoxic effects on tumor cell types. Does not alter culture media. trans-C75 ((±)-C75) inhibits CPT1, and the differential activity of its C75 on enantiomers may lead to the development of possible novel cancer and luminescence medicines [2]. |
| ln Vivo | Ten to twenty-four hours after intraperitoneal injection, C75 inhibited the expression of c-Fos caused by fasting in the paraventricular nucleus (PVN), hypothalamic ischemia region (LHA), and arcuate nucleus (Arc). After intraperitoneal injection of 30 mg/kg C75, within 2 hours, ≥ 95% of the suspended mice had eaten [3]. Mice treated with C75 showed a 50% reduction in body weight and a 32.9% increase in output as a result of mild oxidation. Even in the face of increased amounts of malonyl-CoA, C75 treatment of animal adipocytes, hepatocytes, and human mammary tissue methanol enhances plant oxidation and ATP levels via raising CPT-1 activity [4]. |
| References |
[1]. Inhibition of Fatty Acid Synthase Sensitizes Prostate Cancer Cells to Radiotherapy. [2]. 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. [3]. 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. [4]. 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. |
| Additional Infomation | (2R,3S)-C75 is a 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid that has 2R,3S-configuration. It is an enantiomer of a (2S,3R)-C75. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~83.3 mg/mL (~327.53 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9321 mL | 19.6603 mL | 39.3205 mL | |
| 5 mM | 0.7864 mL | 3.9321 mL | 7.8641 mL | |
| 10 mM | 0.3932 mL | 1.9660 mL | 3.9321 mL |