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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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Differential in radiosensitizing potency of enantiomers of the fatty acid synthase inhibitor C75
Rae C, et al.
Chirality, 29(1), 10-13 (2017)
Song-Hyo Jin et al.
PLoS neglected tropical diseases, 11(6), e0005687-e0005687 (2017-06-22)
Leprosy is a chronic infectious disease that is caused by the obligate intracellular pathogen Mycobacterium leprae (M.leprae), which is the leading cause of all non-traumatic peripheral neuropathies worldwide. Although both myelinating and non-myelinating Schwann cells are infected by M.leprae in
Mauricio Rosas-Ballina et al.
Frontiers in immunology, 11, 131-131 (2020-03-07)
Altered lipid metabolism in macrophages is associated with various important inflammatory conditions. Although lipid metabolism is an important target for therapeutic intervention, the metabolic requirement involved in lipid accumulation during pro-inflammatory activation of macrophages remains incompletely characterized. We show here
Cheulhee Jung et al.
Analytical and bioanalytical chemistry, 408(30), 8583-8591 (2016-04-02)
There are various ways that priming can occur in nucleic acid amplification reactions. While most reactions rely on a primer to initiate amplification, a mechanism for DNA amplification has been developed in which hairpin sequences at the 3' terminus of
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)
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