-C75 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C14H22O4 |
| Exact Mass | 254.151 |
| CAS # | 1234694-22-4 |
| Related CAS # | C75;218137-86-1;trans-C75;191282-48-1 |
| PubChem CID | 6482234 |
| Appearance | Typically exists as solid at room temperature |
| 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]1OC(=O)C(=C)[C@H]1C(=O)O |
| InChi Key | VCWLZDVWHQVAJU-NWDGAFQWSA-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+/m0/s1 |
| Chemical Name | (2S,3R)-4-methylidene-2-octyl-5-oxooxolane-3-carboxylic acid |
| 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 | PC3 cell growth is inhibited by C75, with an IC50 of 35 μM after 24 hours. With an IC50 of 50 μM, C75 (10-50 μM) also inhibits the development of LNCaP spheroids in a concentration-dependent way [1]. Without changing food intake, (-)-C75 cytotoxically affects tumor cell lines and suppresses FAS function. Since (+)-C75 inhibits CPT1 and causes anorexia when administered, it appears that central CPT1 inhibition is necessary for C75's anorexigenic actions. The distinct actions of the C75 enantiomers could result in the creation of novel medications targeted specifically at fat and cancer [2]. |
| ln Vivo | 10–24 hours following intraperitoneal administration, C75 inhibits the expression of c-Fos caused by fasting in the paraventricular nucleus (PVN), lateral hypothalamic region (LHA), and arcuate nucleus (Arc). Within two hours, mice's food intake can be inhibited by up to 95% when given an intraperitoneal injection of 30 mg/kg body weight of C75 [3]. Fatty acid oxidation caused DIO mice administered with C75 to lose 50% of their body weight and boost their energy production by 32.9 percent. Even in the face of high amounts of malonyl-CoA, C75 treatment of rodent adipocytes, hepatocytes, and human breast cancer cells boosts fatty acid oxidation and ATP levels through boosting CPT-1 activity [4]. |
| References |
[1]. Inhibition of Carnitine Palmitoyltransferase 1A Aggravates Fatty Liver Graft Injury via Promoting Mitochondrial Permeability Transition. Transplantation. 2021 Mar 1;105(3):550-560. [2]. Inhibition of Fatty Acid Synthase Sensitizes Prostate Cancer Cells to Radiotherapy. [3]. 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. [4]. 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. [5]. 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 | (2S,3R)-C75 is a 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid that has 2S,3R-configuration. It is an enantiomer of a (2R,3S)-C75. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |