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C5490

Sigma-Aldrich

C75

≥98% (HPLC), powder

Synonym(s):

4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C14H22O4
CAS Number:
218137-86-1
Molecular Weight:
254.32
MDL number:
MFCD03426157
UNSPSC Code:
41121801
PubChem Substance ID:
24892789
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear

storage temp.

2-8°C

SMILES string

CCCCCCCCC1OC(=O)C(=C)C1C(O)=O

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)

InChI key

VCWLZDVWHQVAJU-UHFFFAOYSA-N

Application

C75 has been used:
  • as a fatty acid synthase (FASN) inhibitor to test its ability in the direct inhibition of FASN to attenuate mammosphere formation as compared to metformin
  • as a pharmacological inhibitor to inhibit fatty acid synthesis in glioma stem cells (GSCs)
  • as FAS inhibitor in the pre-treatment of Chang cells to inhibit lipogenesis and reverse the senescence induced by hydrogen peroxide

Biochem/physiol Actions

C75 helps to increase the cancer‐killing capability of ionizing radiation.
C75 is a novel, potent synthetic inhibitor of fatty acid synthase (FAS), which is used as a tool for studying fatty acid synthesis in metabolic disorders and cancer.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sterol regulatory element-binding protein (SREBP)-1-mediated lipogenesis is involved in cell senescence
Kim YM, et al.
Test, 285(38), 29069-29077 (2010)
Michal Matuszewski et al.
Nucleic acids research, 45(4), 2137-2149 (2016-12-04)
N6-Threonylcarbamoyladenosine (t6A) and its derivatives are universally conserved modified nucleosides found at position 37, 3΄ adjacent to the anticodon in tRNAs responsible for ANN codons. These modifications have pleiotropic functions of tRNAs in decoding and protein synthesis. In certain species
Marcelo M Samsa et al.
PLoS pathogens, 5(10), e1000632-e1000632 (2009-10-24)
Dengue virus is responsible for the highest rates of disease and mortality among the members of the Flavivirus genus. Dengue epidemics are still occurring around the world, indicating an urgent need of prophylactic vaccines and antivirals. In recent years, a
Metformin-induced killing of triple-negative breast cancer cells is mediated by reduction in fatty acid synthase via miRNA-193b
Wahdan-Alaswad RS, et al.
Hormones & Cancer, 5(6), 374-389 (2014)
Asuteka Nagao et al.
Nature structural & molecular biology, 24(9), 778-782 (2017-08-08)
The genetic code is not frozen but still evolving, which can result in the acquisition of 'dialectal' codons that deviate from the universal genetic code. RNA modifications in the anticodon region of tRNAs play a critical role in establishing such
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