5-(Tetradecyloxy)-2-furoic acid

HCID 115175

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Basic information

CAS: 54857-86-2
Standard SMILES: CCCCCCCCCCCCCCOc1ccc(C(=O)O)o1
InChIKey: CZRCFAOMWRAFIC-UHFFFAOYSA-N
Molecular formula: C19H32O4
Average molar mass: 324.5 g/mol
Monoisotopic mass: 324.2300595

Names & identifiers

Preferred name: 5-(Tetradecyloxy)-2-furoic acid
IUPAC: 5-tetradecoxyfuran-2-carboxylic acid
English name: 5-(Tetradecyloxy)-2-furoic acid
Molecular formula: C19H32O4
Molecular weight: 324.45

Names & synonyms

TOFA54857-86-25-(Tetradecyloxy)-2-furoic acidOlumacostatRMI-145145-Tetradecyloxy-2-furonic acid5-(Tetradecyloxy)-2-furancarboxylic acid5-(tetradecyloxy)furan-2-carboxylic acid2-Furancarboxylic acid, 5-(tetradecyloxy)-RMI 14,514BI12FRY055DTXSID60203338

Show more names

mdl14514TOFA (RMI14514RMI14514MDL14514TOFA, 10 mM in DMSOTOFA (RMI14514:MDL14514)Sodium benzoate dihydrate5-tetradecyloxy-2-furonicacid5-(TETRADECYLOXY)-2-FUROIC TOFA

RMI-14,514CHEBI:77936RefChem:913224DTXCID601258295-tetradecoxyfuran-2-carboxylic acidTOFA (5-(Tetradecyloxy)-2-furoic acid)AC-8632RMI14514;MDL14514

Database identifiers

CAS: 54857-86-2
PubChem CID: 115175
DTXSID: DTXSID60203338
ChEMBL: CHEMBL1562779
ChEBI: CHEBI:77936
UNII: BI12FRY055
Nikkaji: J395.152I

Properties

Computed structural properties

XLogP: 7.8
Topological polar surface area: 59.7 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 15
Heavy atoms: 23
Formal charge: 0
Complexity: 293

Physicochemical properties

Melting point: 112 · 112-115 °C
Boiling point: 441.7 · 441.7±25.0 °C(Predicted)
Density: 1.003 · 1.003±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: 2.5 mg/mL · DMSO: 2.5 mg/mL
form: solid
pka: 3.55 · 3.55±0.10(Predicted)
color: white to beige
Stability: 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
InChI: 1S/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)
InChIKey: CZRCFAOMWRAFIC-UHFFFAOYSA-N
SMILES: CCCCCCCCCCCCCCOc1ccc(o1)C(O)=O
FDA UNII: 12 FRY055 · BI12FRY055
UNSPSC Code: 41121800 · 41121800
NACRES: 77 · NA.77
PPE: 95 · Eyeshields, Gloves, type N95 (US)
WGK Germany: 2 · 2
RTECS: 288000 · LU0288000
HS Code: 29321900 · 29321900
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 2
rtecs: LU0288000
hs_code: 29321900
Storage Class: 11 - Combustible Solids

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.

Applications · 2 items

DescriptionTOFA (54857-86-2) interferes with fatty acid synthase via inhibition of acetyl Co-A carboxylase (ACC1).1 Induces apoptosis in a variety of tumor cell lines.2,3 Stimulates neurite outgrowth and neuronal differentiation in rat pheochromocytoma cells.4 TOFA impairs glucose-stimulated insulin secretion after chronic treatment.5

UsesTOFA has been used as a lipid biosynthesis inhibitor in mesenchymal stromal cells (MSCs), human pluripotent stem cells., an acetyl-CoA carboxylase 1 inhibitor in murine adipocyte cell lines., a lipolysis inhibitor in cancer stem cells (CSCs).