54857-86-2 Usage
Uses
Used in Pharmaceutical Industry:
5-(TETRADECYLOXY)-2-FUROIC ACID is used as a lipid biosynthesis inhibitor for mesenchymal stromal cells (MSCs) and human pluripotent stem cells. It plays a crucial role in regulating lipid metabolism and has potential applications in the development of treatments for metabolic disorders.
Used in Biochemical Research:
TOFA is used as an acetyl-CoA carboxylase 1 inhibitor in murine adipocyte cell lines. This application aids in understanding the role of ACC1 in fatty acid synthesis and its potential as a therapeutic target for obesity and related metabolic diseases.
Used in Cancer Research and Treatment:
5-(TETRADECYLOXY)-2-FUROIC ACID is used as a lipolysis inhibitor in cancer stem cells (CSCs). By targeting CSCs, TOFA may contribute to the development of novel cancer treatments that specifically target the self-renewal and tumorigenic properties of these cells.
Used in Neurological Research:
TOFA is used to stimulate neurite outgrowth and neuronal differentiation in rat pheochromocytoma cells. This application helps researchers understand the molecular mechanisms underlying neuronal development and may lead to the development of treatments for neurological disorders.
Used in Diabetes Research:
5-(TETRADECYLOXY)-2-FUROIC ACID is used to impair glucose-stimulated insulin secretion after chronic treatment. This application is valuable for studying the effects of TOFA on insulin secretion and its potential role in the development of treatments for diabetes.
Biochem/physiol Actions
5-(Tetradecyloxy)-2-furoic acid (TOFA) elicits hypolipidemic?functionality by favoring fatty acid breakdown and at the same time preventing biosynthesis. It induces apoptosis in pancreatic cancer cells and favors tumor suppression.
References
References/Citations:
1) Halvorson?et al. (1984),?Inhibition of fatty acid synthesis in isolated adipocytes by 5-tetradecyloxy)-2-furoic acid; Lipids,?19?851
2) Guseva?et al. (2011),?TOFA (5-tetradecyl-oxy-2-furoic acid) reduces fatty acid synthesis, inhibits expression of AR, neuropilin-1 and Mcl-1 and kills prostate cancer cells independent of p53 status; Cancer Biol. Ther.,?12?80
3) Zhou?et al. (2003),?Fatty acid synthesis inhibition triggers apoptosis during S phase in human cancer cells; Cancer Res.,?63?7330
4) Schmidt?et al. (1999),?Transcription control and neuronal differentiation by agents that activate the LXR nuclear receptor family; Mol. Cell. Endocrinol.,?155?51
5) Ronnebaum?et al. (2008),?Chronic suppression of acetyl-CoA carboxylase 1 in beta-cells impairs insulin secretion via inhibition of glucose rather than lipid metabolism; J. Biol. Chem.,?283?14248
Check Digit Verification of cas no
The CAS Registry Mumber 54857-86-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,8,5 and 7 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 54857-86:
(7*5)+(6*4)+(5*8)+(4*5)+(3*7)+(2*8)+(1*6)=162
162 % 10 = 2
So 54857-86-2 is a valid CAS Registry Number.
InChI:InChI=1/C19H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22-18-15-14-17(23-18)19(20)21/h14-15H,2-13,16H2,1H3,(H,20,21)
54857-86-2Relevant academic research and scientific papers
DERMATOLOGICAL FORMULATIONS OF 2-(2-ETHOXY-2-OXOETHYL)(METHYL)AMINO-2-OXOETHYL 5-(TETRADECYLOXY)FURAN-2-CARBOXYLATE
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Page/Page column 28-31, (2018/02/28)
Disclosed herein are dermatological formulations comprising low-impurity TOFA prodrug 2-(2-ethoxy-2-oxoethyl)(methyl)amino-2-oxoethyl 5-(tetradecyloxy)furan-2-carboxylate represented by Formula (la) and pharmaceutical use thereof.
SYNTHETIC PROCESS FOR PREPARING 2-FUROIC ACID DERIVATIVES
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Paragraph 0075-0081, (2016/09/12)
Disclosed herein are processes for forming 2-furoic acid derivatives represented by Formula (I):
Antiretroviral furan ketones
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, (2008/06/13)
Furan ketone derivatives thereof having antiretrovirus activity and effective in a method of treatment of a retrovirus infection, have the formula STR1 wherein Y is a bond, oxygen or divalent sulfur; n is 0 or 1; R is a straight or branched C8-20 alkyl chain or a straight or branched C8-20 alkenyl chain having from 1 to 4 double bonds; and R1 is C1-6 alkyl.
Antirhinovirus agents
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, (2008/06/13)
Compounds of the following general structure are useful as antirhinovirus agents: STR1 wherein R is a straight or branched hydrocarbon chain having from 12 to 16 carbon atoms and is saturated or is unsaturated having from 1 to 4 double bonds.
Hypolipidemic agents RO- or RS- substituted furoic acids, esters and salts
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, (2008/06/13)
Substituted furoic acids and esters and pharmaceutically acceptable salts thereof of the following general structure are useful as hypolipidemic agents: STR1 wherein Y represents oxygen or divalent sulfur; R represents a straight or branched alkyl chain containing from 10 to 20 carbon atoms and may be saturated or may be unsaturated containing from 1 to 4 double bonds; R1 represents hydrogen, straight or branched lower alkyl of from 1 to 6 carbon atoms, benzyl, phenethyl, pyridylmethyl, alkane-poly-yl containing from 3 to 6 carbon atoms, 1,2,3,4,5,6-cyclohexanehexayl, or Z; Z represents (A) the group STR2 wherein n is an integer of 2 or 3; R2 represents straight or branched lower alkyl of from 1 to 4 carbon atoms, or acyl; R3 represents hydrogen or straight or branched lower alkyl of from 1 to 4 carbon atoms with the proviso that when R3 is hydrogen, R2 is acyl; or when R2 is other than acyl, R2 and R3 taken together with the nitrogen atom to which each is attached form a monocyclic heterocyclic group, such as pyrrolidino, piperidino, morpholino, or piperazino; or (B) the group STR3 WHEREIN THE SUM OF THE INTEGERS M AND P IS EQUAL TO FROM 3 TO 5; AND R4 represents straight or branched lower alkyl of from 1 to 4 carbon atoms; X is an integer of from 1 to 6 with the proviso that when R1 is alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to from 2 to 6, and when R1 is other than alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to 1.
