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dodecanedioic acid
decamethylenedicarboxylic acid

Supplier Sponsors

Name:dodecanedioic acid
CAS Number: 693-23-2Picture of molecule3D/inchi
Other(deleted CASRN):142610-44-4
ECHA EINECS - REACH Pre-Reg:211-746-3
FDA UNII:978YU42Q6I
Nikkaji Web:J43.533C
Beilstein Number:1782580
MDL:MFCD00002735
XlogP3:3.20 (est)
Molecular Weight:230.30414000
Formula:C12 H22 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:cosmetic ingredient for skin conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
DG SANTE Food Contact Materials:dodecanedioic acid
FDA Mainterm (IAUFC):693-23-2 ; DODECANEDIOIC ACID
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 128.00 °C. @ 760.00 mm Hg
Boiling Point: 393.98 °C. @ 760.00 mm Hg (est)
Flash Point: 422.00 °F. TCC ( 216.60 °C. ) (est)
logP (o/w): 2.920 (est)
Soluble in:
 water, 40 mg/L @ 20 °C (exp)
 water, 146.4 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
BOC Sciences
For experimental / research use only.
Dodecanedioic acid
EMD Millipore
For experimental / research use only.
Dodecanedioic Acid
Santa Cruz Biotechnology
For experimental / research use only.
Dodecanedioic Acid 99%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Dodecanedioic Acid 99%
Silver Fern Chemical
Dodecanedioic Acid (DDDA)
Odor: characteristic
Use: Dodecanedioic acid (DDDA) is a pure C12 dibasic acid that is mainly used in antiseptics, painting materials, top-grade coatings, corrosion inhibitors, surfactants and engineering plastics. It is available in a white, flaky form and has a long shelf life of approximately 3 years, depending on the storage methods.
TCI AMERICA
For experimental / research use only.
Dodecanedioic Acid >99.0%(GC)
United International
Dodecanedioic Acid
 
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:
cosmetic ingredient for skin conditioning
Recommendation for dodecanedioic acid usage levels up to:
 not for fragrance use.
 
Recommendation for dodecanedioic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):693-23-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :12736
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:nwg
dodecanedioic acid
Chemidplus:0000693232
RTECS:JR2370000 for cas# 693-23-2
 
References:
 dodecanedioic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:693-23-2
Pubchem (cid):12736
Pubchem (sid):134976252
 
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
FDA Indirect Additives used in Food Contact Substances:View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C02678
HMDB (The Human Metabolome Database):HMDB00623
FooDB:FDB022148
Export Tariff Code:2921.30.3000
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 corfree M2
 decamethylenedicarboxylic acid
1,10-decane dicarboxylic acid
1,10-decanedicarboxylic acid
 

Articles:

PubMed:Synthesis and Biological Evaluation of 5'-O-Dicarboxylic Fatty Acyl Monoester Derivatives of Anti-HIV Nucleoside Reverse Transcriptase Inhibitors.
PubMed:Identification of unknown impurity of azelaic acid in liposomal formulation assessed by HPLC-ELSD, GC-FID, and GC-MS.
PubMed:Peptide-based MRI contrast agent and near-infrared fluorescent probe for intratumoral legumain detection.
PubMed:Effect of ginseng polysaccharide on the urinary excretion of type 2 diabetic rats studied by liquid chromatography-mass spectrometry.
PubMed:Use of dicarboxylic acids in type 2 diabetes.
PubMed:The role of surface charge on the uptake and biocompatibility of hydroxyapatite nanoparticles with osteoblast cells.
PubMed:Direct electrospray ionization mass spectrometry quantitative analysis of sebacic and terephthalic acids in biodegradable polymers.
PubMed:Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol.
PubMed:[Effect of a novel injectable hydrogel implant on ventricular remodeling in rabbits with experimental myocardial infarction].
PubMed:Poly(glycerol-dodecanoate), a biodegradable polyester for medical devices and tissue engineering scaffolds.
PubMed:Medium-chain fatty acids and glutathione derivatives as inhibitors of S-nitrosoglutathione reduction mediated by alcohol dehydrogenase 3.
PubMed:Bone marrow stem cells implantation with alpha-cyclodextrin/MPEG-PCL-MPEG hydrogel improves cardiac function after myocardial infarction.
PubMed:Occupational asthma to gel flux containing dodecanedioic acid.
PubMed:Determination of higher carboxylic acids in snow samples using solid-phase extraction and LC/MS-TOF.
PubMed:Fabrication of supramolecular hydrogels for drug delivery and stem cell encapsulation.
PubMed:Different oxidized phospholipid molecules unequally affect bilayer packing.
PubMed:Antitumor efficacy of poly(dimer acid-dodecanedioic acid) copolymer in mice bearing Sarcoma-180 tumor.
PubMed:Dodecanedioic acid overcomes metabolic inflexibility in type 2 diabetic subjects.
PubMed:Polycondensation of dicarboxylic acids and diols in water catalyzed by surfactant-combined catalysts and successive chain extension.
PubMed:Synthesis, characterization of novel injectable drug carriers and the antitumor efficacy in mice bearing Sarcoma-180 tumor.
PubMed:Novel metabolic and molecular findings in hepatic carnitine palmitoyltransferase I deficiency.
PubMed:alpha,omega-Dicarboxylic acid accumulation by acyl-CoA oxidase deficient mutants of Yarrowia lipolytica.
PubMed:Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of alpha,omega-alkanedithiols.
PubMed:Approximate linear confidence and curvature of a kinetic model of dodecanedioic acid in humans.
PubMed:Stochastic vs. deterministic uptake of dodecanedioic acid by isolated rat livers.
PubMed:Preparation of dodecanol-tolerant strains of Yarrowia lipolytica.
PubMed:Temporal dynamics and degradation activity of an bacterial inoculum for treating waste metal-working fluid.
PubMed:Effects of fluid composition on mist composition.
PubMed:[Effect of sugars and pH on the fermentation of decane 1,10-dicarboxylic acid].
PubMed:Macrocyclic musk compounds--an absence of genotoxicity in the Ames test and the in vivo Micronucleus assay.
PubMed:Synthesis of D-mannitol and L-iditol derivatives as monomers for the preparation of new regioregular AABB-type polyamides.
PubMed:Cloning and characterization of a gene cluster for cyclododecanone oxidation in Rhodococcus ruber SC1.
PubMed:Oxidation of D-[U-(14)C] glucose and [1,12-(14)C] dodecanedioic acid by pancreatic islets from Goto-Kakizaki rats.
PubMed:Oxidation of [1,12-14C]dodecanedioic acid by rat pancreatic islets.
PubMed:Candida cloacae oxidation of long-chain fatty acids to dioic acids.
PubMed:Structure of the inclusion complex of beta-cyclodextrin with 1,12-dodecanedioic acid using synchrotron radiation data; a detailed dimeric beta-cyclodextrin structure
PubMed:Disposition of dodecanedioic acid in humans.
PubMed:A new HPLC method for the direct analysis of triglycerides of dicarboxylic acids in biological samples.
PubMed:10-Undecynoic acid, an inhibitor of cytochrome P450 4A1, inhibits ethanolamine-specific phospholipid base exchange reaction in rat liver microsomes.
PubMed:Comparison between dodecanedioic acid and long-chain triglycerides as an energy source in liquid formula diets.
PubMed:Kinetics of dodecanedioic acid triglyceride in rats.
PubMed:Positive feedback between ethanolamine-specific phospholipid base exchange and cytochrome P450 activities in rat liver microsomes. The effect of clofibric acid.
PubMed:The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients.
PubMed:Dodecanedioic acid infusion induces a sparing effect on whole-body glucose uptake, mainly in non-insulin-dependent diabetes mellitus.
PubMed:Kinetics of dodecanedioic acid and effect of its administration on glucose kinetics in rats.
PubMed:Uptake of dodecanedioic acid by isolated rat liver.
PubMed:Effects of steric bulk and conformational rigidity on fatty acid omega hydroxylation by a cytochrome P450 4A1 fusion protein.
PubMed:The omega-hydroxlyation of lauric acid: oxidation of 12-hydroxlauric acid to dodecanedioic acid by a purified recombinant fusion protein containing P450 4A1 and NADPH-P450 reductase.
PubMed:Active site structure and substrate specificity of cytochrome P450 4A1: steric control of ligand approach perpendicular to heme plane.
PubMed:Production of useful chemicals from sunflower oil by microbial biotransformation with rhizopus stolonifer NRRL 1478.
PubMed:Plasma clearance and oxidation of dodecanedioic acid in humans.
PubMed:Pharmacokinetic analysis of dodecanedioic acid in humans from bolus data.
PubMed:Extraction of mono- and dicarboxylic acids from a curative water.
PubMed:In vivo reconstitution of highly active Candida maltosa cytochrome P450 monooxygenase systems in inducible membranes of Saccharomyces cerevisiae.
PubMed:Dicarboxylic acids, an alternate fuel substrate in parenteral nutrition: an update.
PubMed:Fenofibrate: metabolism and species differences for peroxisome proliferation in cultured hepatocytes.
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:Pharmacokinetic profile of dodecanedioic acid, a proposed alternative fuel substrate.
PubMed:Cytochrome P450BM-3 (CYP102): regiospecificity of oxidation of omega-unsaturated fatty acids and mechanism-based inactivation.
PubMed:Acyl, pseudotetra-, tri- and dipeptide active-core analogs of insect neuropeptides.
PubMed:Characteristics and subcellular localization of pristanoyl-CoA synthetase in rat liver.
PubMed:Induction of omega-oxidation of monocarboxylic acids in rats by acetylsalicylic acid.
PubMed:Characterization of the binding sites for dicarboxylic acids on bovine serum albumin.
PubMed:cDNA cloning and expression of the mRNA for cytochrome P-450kd which shows a fatty acid omega-hydroxylating activity.
PubMed:Metabolic conversion of dicarboxylic acids to succinate in rat liver homogenates. A stable isotope tracer study.
PubMed:Metabolism of dicarboxylic acids in rat hepatocytes.
PubMed:The oxidation of dicarboxylic acid CoA esters via peroxisomal fatty acyl-CoA oxidase.
PubMed:Production of dodecanedioic acid from n-dodecane by yeasts.
PubMed:Free acetate production by rat hepatocytes during peroxisomal fatty acid and dicarboxylic acid oxidation.
PubMed:Rat liver metabolism of dicarboxylic acids.
PubMed:Comparison between the formation and the oxidation of dicarboxylylcarnitine esters in rat liver and skeletal muscle: possible implications for human inborn disorders of mitochondrial beta-oxidation.
PubMed:Comparison of the metabolism of dodecanedioic acid in vivo in control, riboflavin-deficient and clofibrate-treated rats.
PubMed:In situ metabolism of 1,omega medium chain dicarboxylic acids in the liver of intact rats as detected by 13C and 1H NMR.
PubMed:Metabolism of dicarboxylic acids in vivo and in the perfused kidney of the rat.
PubMed:Influence of sodium salts of saturated medium chain length (C6, C9, C10 and C12) dicarboxylic acids on the uterine horn of rat in vitro.
PubMed:Effect of acetylsalicylic acid on fatty acid omega-hydroxylation in rat liver.
PubMed:Observations on cell kinetics and viability of a human melanoma cell line exposed to dicarboxylic acids in tissue culture.
PubMed:In vitro studies on the oxidation of medium-chain dicarboxylic acids in rat liver.
PubMed:Effects of dicarboxylic acids on normal and malignant melanocytes in culture.
PubMed:Fast events in single-channel currents activated by acetylcholine and its analogues at the frog muscle end-plate.
PubMed:The microsomal dicarboxylyl-CoA synthetase.
PubMed:Effect of dicarboxylic acids on Harding-Passey and Cloudman S91 melanoma cells in tissue culture.
PubMed:Analytical, ultrastructural, autoradiographic and biochemical studies on [3H]dicarboxylic acid added to cultures of melanoma cells.
PubMed:Inhibition of cold insolubility of an IgA cryoglobulin by decanedicarboxylic acid and related compounds.
PubMed:Metabolism of straight saturated medium chain length (C9 to C12) dicarboxylic acids.
PubMed:General (medium-chain) acyl-CoA dehydrogenase deficiency (non-ketotic dicarboxylic aciduria): quantitative urinary excretion pattern of 23 biologically significant organic acids in three cases.
PubMed:Cyanide-insensitive and clofibrate enhanced beta-oxidation of dodecanedioic acid in rat liver. An indication of peroxisomal beta-oxidation of N-dicarboxylic acids.
 
Notes:
Dodecanedioic acid is a dicarboxylic acid which is water soluble and involves in a metabolic pathway intermediate to those of lipids and carbohydrates. (PMID 9591306). Dodecanedioid acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency. CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. This C12 dicarboxylic aciduria suggests that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes. (PMID: 16146704) [HMDB]
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