| Identification | Back Directory | [Name]
C75 | [CAS]
191282-48-1 | [Synonyms]
C75
C75 (trans)
C75 (racemic)
C 75 trC-75 trans-racemic
4-METHYLENE-2-OCTYL-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID
TETRAHYDRO-4-METHYLENE-2-OCTYL-5-OXO-3-FURANCARBOXYLIC ACID
(2R,3S)-4-METHYLIDENE-5-OXO-2-N-OCTYL-OXOLANE-3-CARBOXYLIC ACID
trans-4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid
trans-Tetrahydro-4-Methylene-2-octyl-5-oxo-3-furancarboxylic Acid
(2S,3R)-4-methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid
(2R*,3S*)-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylicacid
(2R,3S)-rel-Tetrahydro-4-Methylene-2-octyl-5-oxo-3-furancarboxylic Acid
3-Furancarboxylic acid, tetrahydro-4-methylene-2-octyl-5-oxo-, (2R,3S)-rel-
trans-C 75 (trans-4-Methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid) | [Molecular Formula]
C14H22O4 | [MDL Number]
MFCD03426157 | [MOL File]
191282-48-1.mol | [Molecular Weight]
254.32 |
| Chemical Properties | Back Directory | [Boiling point ]
432.1±45.0 °C(Predicted) | [density ]
1.08±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: 18 mg/mL
| [form ]
solid
| [pka]
3.08±0.40(Predicted) | [color ]
off-white
|
| Hazard Information | Back Directory | [Uses]
trans-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylic Acid is a well-known fatty acid synthase (FAS) inhibitor. Studies show that trans-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylic Ac
id is a cell cycle arrest inducer in hepatocellular carcinoma (HCC) cell lines. It has also been shown to blocks resistin-induced increases in lipid accumulation by human macrophages. | [Definition]
ChEBI: (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. | [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]. | [storage]
Store at +4°C | [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. |
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