hexadecane dioic acid
thapsic acid
Identification
| Name | hexadecane dioic acid |
| IUPAC | hexadecanedioic acid |
| CAS Number | 505-54-4 |
| EINECS | 208-013-5 |
| FDA UNII | Search |
| Molecular Formula | C16 H30 O4 |
| Molecular Weight | 286.41190000 |
| MDL Number | MFCD00002746 |
| Nikkaji Number | J11.794C |
| Beilstein | 1792831 |
| XlogP3 | 5.40 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 457.50 °C. @ 760.00 mm Hg (est) |
| Flash Point | 472.00 °F. TCC ( 244.60 °C. ) (est) |
| logP (o/w) | 5.050 (est) |
| Soluble in | water, 1.494 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for hexadecane dioic acid usage levels up to | not for fragrance use. |
| Recommendation for hexadecane dioic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
hexadecane-1,16-dioic acid
hexadecanedioic acid
1,14-
tetradecane dicarboxylic acid
tetradecane-omega,omega'-dicarboxylic acid
thapsic acid
PubMed:
A permeability transition in liver mitochondria and liposomes induced by α,Ï-dioic acids and Ca(2+)
PubMed:
Induction of Ca2+-Dependent Cyclosporin A-Insensitive Nonspecific Permeability of the Inner Membrane of Liver Mitochondria and Cytochrome c Release by α,Ï-Hexadecanedioic Acid in Media of Varying Ionic Strength.
PubMed:
Long-chain α,Ï-dioic acids as inducers of cyclosporin A-insensitive nonspecific permeability of the inner membrane of liver mitochondria loaded with calcium or strontium ions.
PubMed:
Lipid profiling for early diagnosis and progression of colorectal cancer using direct-infusion electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry.
PubMed:
Suppression of adipose lipolysis by long-chain fatty acid analogs.
PubMed:
Stable vesicles composed of monocarboxylic or dicarboxylic fatty acids and trimethylammonium amphiphiles.
PubMed:
Analysis of the hibernation cycle using LC-MS-based metabolomics in ground squirrel liver.
PubMed:
Synthesis and bio-evaluation of a new fatty acid derivative for myocardial imaging.
PubMed:
Amino-modified diamond as a durable stationary phase for solid-phase extraction.
PubMed:
Hexadecanedionic acid-sepharose 4B: A new tool for preparation of albumin-depleted plasma.
PubMed:
Modulation of insulin secretion by fatty acyl analogs.
PubMed:
Transcriptional regulation of human microsomal triglyceride transfer protein by hepatocyte nuclear factor-4alpha.
PubMed:
Condensation reactions and formation of amides, esters, and nitriles under hydrothermal conditions.
PubMed:
Alkyl and carboxylalkyl esters of 4'-demethyl-4-deoxypodophyllotoxin: synthesis, cytotoxic, and antitumor activity.
PubMed:
Cutin and suberin monomers are membrane perturbants.
PubMed:
Structural study on polymorphism of long-chain dicarboxylic acids using oblique transmission method for micro FT-IR spectrometers.
PubMed:
A new enzyme immunoassay for aconitine and its application to quantitative determination of aconitine levels in plasma.
PubMed:
Oxygenation cascade in conversion of n-alkanes to alpha,omega-dioic acids catalyzed by cytochrome P450 52A3.
PubMed:
Sensitization to insulin induced by beta,beta'-methyl-substituted hexadecanedioic acid (MEDICA 16) in obese Zucker rats in vivo.
PubMed:
Mode of action of peroxisome proliferators as hypolipidemic drugs. Suppression of apolipoprotein C-III.
PubMed:
Dicarboxylic acids affect the growth of dermatophytes in vitro.
PubMed:
Coordinate induction of hepatic fatty acyl-CoA oxidase and P4504A1 in rat after activation of the peroxisome proliferator-activated receptor (PPAR) by sulphur-substituted fatty acid analogues.
PubMed:
Cytochrome P450BM-3 (CYP102): regiospecificity of oxidation of omega-unsaturated fatty acids and mechanism-based inactivation.
PubMed:
On the mechanism of the hypolipidemic effect of sulfur-substituted hexadecanedioic acid (3-thiadicarboxylic acid) in normolipidemic rats.
PubMed:
Induction of peroxisomal fatty acid beta-oxidation and liver fatty acid-binding protein by peroxisome proliferators. Mediation via the cytochrome P-450IVA1 omega-hydroxylase pathway.
PubMed:
Hypocholesterolaemic effect of beta beta'-methyl-substituted hexadecanedioic acid (MEDICA 16) in the male hamster.
PubMed:
Tissue selective modulation of redox and phosphate potentials by beta,beta'-methyl-substituted hexadecanedioic acid.
PubMed:
Effect of beta, beta'-tetramethyl-substituted hexadecanedioic acid (MEDICA 16) on laying hen performance and egg yolk lipid composition.
PubMed:
Biogenesis of dicarboxylic acids in rat liver homogenate studied by 13C labeling.
PubMed:
Characterization of the binding sites for dicarboxylic acids on bovine serum albumin.
PubMed:
Hypolipidemic effect of beta, beta'-tetramethyl hexadecanedioic acid (MEDICA 16) in hyperlipidemic JCR:LA-corpulent rats.
PubMed:
Inhibition of rat liver acetyl-CoA carboxylase by beta, beta'-tetramethyl-substituted hexadecanedioic acid (MEDICA 16).
PubMed:
Alkylthio acetic acids (3-thia fatty acids)--a new group of non-beta-oxidizable peroxisome-inducing fatty acid analogues--II. Dose-response studies on hepatic peroxisomal- and mitochondrial changes and long-chain fatty acid metabolizing enzymes in rats.
PubMed:
Alkylthioacetic acids (3-thia fatty acids) as non-beta-oxidizable fatty acid analogues: a new group of hypolipidemic drugs. III. Dissociation of cholesterol- and triglyceride-lowering effects and the induction of peroxisomal beta-oxidation.
PubMed:
Alkylthioacetic acid (3-thia fatty acids)--a new group of non-beta-oxidizable, peroxisome-inducing fatty acid analogues. I. A study on the structural requirements for proliferation of peroxisomes and mitochondria in rat liver.
PubMed:
Adipose reduction by beta,beta'-tetramethyl-substituted hexadecanedioic acid (MEDICA 16).
PubMed:
Hypolipidemic, antiobesity, and hypoglycemic-hypoinsulinemic effects of beta,beta'-methyl-substituted hexadecanedioic acid in sand rats.
PubMed:
The induction of liver peroxisomal proliferation by beta,beta'-methyl-substituted hexadecanedioic acid (MEDICA 16).
PubMed:
The hypochylomicronemic effect of beta,beta'-methyl-substituted hexadecanedioic acid (MEDICA 16) is mediated by a decrease in apolipoprotein C-III.
PubMed:
Hypolipidemic effect of beta, beta'-methyl-substituted hexadecanedioic acid (MEDICA 16) in normal and nephrotic rats.
PubMed:
The biological origin of ketotic dicarboxylic aciduria. II. In vivo and in vitro investigations of the beta-oxidation of C8-C16-dicarboxylic acids in unstarved, starved and diabetic rats.
PubMed:
The biological origin of ketotic dicarboxylic aciduria. In vivo and in vitro investigations of the omega-oxidation of C6-C16-monocarboxylic acids in unstarved, starved and diabetic rats.
PubMed:
Synthesis and biologic distribution of mercapto derivatives of palmitic acid.
PubMed:
[Acyl-CoA synthetase activity of long-chain mono and dicarboxylic acid in beef liver preparations (author's transl)].
PubMed:
Subcellular localization of hexadecanedioic acid activation in human liver.
PubMed:
In vitro studies on the metabolism of hexadecanedioic acid and its mono-L-carnitine ester.