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hexadecane dioic acid
thapsic acid

Supplier Sponsors

Name:hexadecanedioic acid
CAS Number: 505-54-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-013-5
FDA UNII: Search
Nikkaji Web:J11.794C
Beilstein Number:1792831
MDL:MFCD00002746
XlogP3:5.40 (est)
Molecular Weight:286.41190000
Formula:C16 H30 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
1,14-Tetradecanedicarboxylic Acid 95%
Santa Cruz Biotechnology
For experimental / research use only.
Hexadecanedioic Acid
Sigma-Aldrich: Aldrich
For experimental / research use only.
Hexadecanedioic Acid 96%
sds
TCI AMERICA
For experimental / research use only.
Hexadecanedioic Acid >97.0%(GC)(T)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):505-54-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10459
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
hexadecanedioic acid
Chemidplus:0000505544
 
References:
 hexadecanedioic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10459
Pubchem (sid):134976297
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C19615
HMDB (The Human Metabolome Database):HMDB00672
FooDB:FDB003049
Export Tariff Code:2917.12.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 cherry sweet cherry
Search Trop Picture
 potato leaf
Search Trop Picture
 
Synonyms:
 hexadecane-1,16-dioic acid
 hexadecanedioic acid
1,14-tetradecane dicarboxylic acid
 tetradecane-omega,omega'-dicarboxylic acid
 thapsic acid
 

Articles:

PubMed:A permeability transition in liver mitochondria and liposomes induced by α,ω-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,ω-Hexadecanedioic Acid in Media of Varying Ionic Strength.
PubMed:Long-chain α,ω-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.
 
Notes:
Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in liver (PMID 4372285). It has an antitumor activity (PMID 14987827).
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