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Category:pharmaceuticals / chemical synthisis
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Melting Point: | 106.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 342.00 °C. @ 760.00 mm Hg
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| Flash Point: | 359.00 °F. TCC ( 181.90 °C. ) (est)
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| logP (o/w): | 0.610 |
| Soluble in: |
| | water, 5.00E+04 mg/L @ 20 °C (exp) | | | water, 5.112e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
oral-mouse LD50 4800 mg/kg
Biochemical Journal. Vol. 34, Pg. 1196, 1940.
oral-rat LD50 7000 mg/kg
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 477, 1969.
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | pharmaceuticals / chemical synthisis |
| Recommendation for pimelic acid usage levels up to: | | | not for fragrance use.
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| Recommendation for pimelic acid flavor usage levels up to: |
| | not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
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Scientific Report of EFSA on the risk assessment of salts of authorised acids, phenols or alcohols for use in food contact materials [1]
View page or View pdf
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| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):111-16-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :385 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| heptanedioic acid |
| Chemidplus:0000111160 |
| RTECS:TK3677000 for cas# 111-16-0 |
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| 6- | carboxyhexanoic acid | | | dimelic acid | | | heptandioic acid | | | heptane dioic acid | | | heptane-1,7-dioic acid | | | heptanedioic acid | | 1,7- | heptanedioic acid | | | heptanedioicacid | | 1,5- | pentane dicarboxylic acid | | | pentane-1,5-dicarboxylic acid | | 1,5- | pentanedicarboxylic acid | | | pileric acid | | | pimelate |
Articles:
| PubMed:Arabidopsis ENHANCED DISEASE SUSCEPTIBILITY1 promotes systemic acquired resistance via azelaic acid and its precursor 9-oxo nonanoic acid. |
| PubMed:Engineering biotin prototrophic Corynebacterium glutamicum strains for amino acid, diamine and carotenoid production. |
| PubMed:Salt and cocrystals of sildenafil with dicarboxylic acids: solubility and pharmacokinetic advantage of the glutarate salt. |
| PubMed:Size dependence of the structure of organic aerosol. |
| PubMed:Reducing mechanical activation-induced amorphisation of salbutamol sulphate by co-processing with selected carboxylic acids. |
| PubMed:Eight Zn(II) coordination networks based on flexible 1,4-di(1H-imidazol-1-yl)butane and different dicarboxylates: crystal structures, water clusters, and topologies. |
| PubMed:Development of biotin-prototrophic and -hyperauxotrophic Corynebacterium glutamicum strains. |
| PubMed:Lipid profiling of the Arabidopsis hypersensitive response reveals specific lipid peroxidation and fragmentation processes: biogenesis of pimelic and azelaic acid. |
| PubMed:Contributions of the peroxisome and β-oxidation cycle to biotin synthesis in fungi. |
| PubMed:Pimelic acid-urea (1/2). |
| PubMed:A Fast Degrading Odd-Odd Aliphatic Polyester-5,7 Made by Condensation Polymerization for Biomedical Applications. |
| PubMed:UPLC-MS-based urine metabolomics reveals indole-3-lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. |
| PubMed:Two dimensional self-assembly of bis-acylureas having various functional end groups. |
| PubMed:Atomic layer deposition of organic-inorganic hybrid materials based on saturated linear carboxylic acids. |
| PubMed:Synthesis of the α,ω-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway. |
| PubMed:Biotin synthesis begins by hijacking the fatty acid synthetic pathway. |
| PubMed:Selectivity in a barren landscape: the P450(BioI)-ACP complex. |
| PubMed:Identification of noninvasive biomarkers for alcohol-induced liver disease using urinary metabolomics and the Ppara-null mouse. |
| PubMed:Aerosol volatility and enthalpy of sublimation of carboxylic acids. |
| PubMed:Tetralin-induced and ThnR-regulated aldehyde dehydrogenase and beta-oxidation genes in Sphingomonas macrogolitabida strain TFA. |
| PubMed:Intrapituitary expression and regulation of the gp130 cytokine interleukin-6 and its implication in pituitary physiology and pathophysiology. |
| PubMed:Three polymorphic forms of the co-crystal 4,4'-bipyridine/pimelic acid and their structural, thermal, and spectroscopic characterization. |
| PubMed:Fermentation characteristics and microbial growth promoted by diets including two-phase olive cake in continuous fermenters. |
| PubMed:(Heptanedioato-κO,O')bis-(1,10-phenanthroline-κN,N')zinc(II) hexa-hydrate. |
| PubMed:A dinuclear lanthanide complex for the recognition of bis(carboxylates): formation of terbium(III) luminescent self-assembly ternary complexes in aqueous solution. |
| PubMed:Synthesis and monoamine transporter binding properties of 2,3-cyclo analogues of 3beta-(4'-aminophenyl)-2beta-tropanemethanol. |
| PubMed:Biological significance and development of practical synthesis of biotin. |
| PubMed:Carbon-carbon bond cleavage by cytochrome p450(BioI)(CYP107H1). |
| PubMed:X-ray studies on crystalline complexes involving amino acids and peptides. XLI. Commonalities in aggregation and conformation revealed by the crystal structures of the pimelic acid complexes of L-arginine and DL-lysine. |
| PubMed:Structural phases of hexamethylenetetramine-pimelic acid (1/1): a unified description based on a stacking model. |
| PubMed:Gas chromatography-mass spectrometry profile of urinary organic acids of Wistar rats orally treated with ozonized unsaturated triglycerides and ozonized sunflower oil. |
| PubMed:Infrared spectra of the hydrogen bond in pimelic acid crystals: polarization and temperature effects. |
| PubMed:Selective nucleation and discovery of organic polymorphs through epitaxy with single crystal substrates. |
| PubMed:Expression, purification, and characterization of BioI: a carbon-carbon bond cleaving cytochrome P450 involved in biotin biosynthesis in Bacillus subtilis. |
| PubMed:Purification, characterization, DNA sequence and cloning of a pimeloyl-CoA synthetase from Pseudomonas mendocina 35. |
| PubMed:Cloning, sequencing, and characterization of the Bacillus subtilis biotin biosynthetic operon. |
| PubMed:Origin of carbon atoms of biotin. 13C-NMR studies on biotin biosynthesis in Escherichia coli. |
| PubMed:Anaerobic degradation of pimelate by newly isolated denitrifying bacteria. |
| PubMed:Biotin biosynthesis in higher plant cells. Identification of intermediates. |
| PubMed:Biotin formation by recombinant strains of Escherichia coli: influence of the host physiology. |
| PubMed:In vivo metabolism of 2,2'-diaminopimelic acid from gram-positive and gram-negative bacterial cells by ruminal microorganisms and ruminants and its use as a marker of bacterial biomass. |
| PubMed:Metabolism of deuterium-labeled nonanoic acids in the riboflavin-deficient rat model of multiple acyl-CoA dehydrogenase deficiency. |
| PubMed:Biosynthesis of biotin-vitamers by family Enterobacteriaceae. |
| PubMed:[10-Acyldithranol dimers; new derivatives of the antipsoriatic dithranol; synthesis, characterization and biochemical properties]. |
| PubMed:Humoral immune response to Bacteroides gingivalis fimbrial antigen in mice. |
| PubMed:The "survival hormones": azelaic and pimelic acids, suppress the stress elicited by isolation conditions on the steroids and phospholipids of adult worker honeybees. |
| PubMed:Determination of murein precursors during the cell cycle of Escherichia coli. |
| PubMed:Azelaic acid--biochemistry and metabolism. |
| PubMed:In vitro metabolism of 2,2'-diaminopimelic acid from gram-positive and gram-negative bacterial cells by ruminal protozoa and bacteria. |
| PubMed:Formation of a biotin precursor, pimelic acid, in yeasts from C18 fatty acids. |
| PubMed:Complement activation in experimental IgA nephropathy: an antigen-mediated process. |
| PubMed:Composition of IgA immune complexes precipitated with polyethylene glycol. A model for isolation and analysis of immune complexes. |
| PubMed:Neurotoxic action of kainic acid in the isolated toad and goldfish retina: II. Mechanism of action. |
| PubMed:The analysis of thiodiglycollic acid by selected ion monitoring. |
| PubMed:[The effect of cellulose on endogenous nitrogen excretion in rats, evaluated using N-15 technics]. |
| PubMed:[Protein and amino acid metabolism in the digestive tract growing young bulls. 1. Flow of bacterial raw protein in the duodenum determined by 2,6-diaminopimelic acid as a marker]. |
| PubMed:Biosynthesis of biotin-vitamers from unsaturated higher fatty acids by bacteria. |
| PubMed:Turnover of the cell wall peptidoglycan during growth of Neisseria gonorrhoeae and Escherichia coli. Relative stability of newly synthesized material. |
| PubMed:[The bacterial fraction in swine feces]. |
| PubMed:Metabolism of alpha-terpineol by Pseudomonas incognita. |
| PubMed:[Determination of fecal bacterial nitrogen in rats]. |
| PubMed:[Effect of guar flour on endogenous nitrogen excretion in rats determined by the 15N-tracer technic]. |
| PubMed:Urinary metabolites of some alicyclic nitrosamines. |
| PubMed:On the effect of aliphatic saturated dicarboxylic acids on anaerobic glycolysis in chicken embryo. |
| PubMed:[Protein and amino acid digestibility in various sections of the intestines in swine. 3. Amino acid composition of chyme and fecal proteins]. |
| PubMed:[Effect of the content of plant crude protein in the ration on the utilization of urea by the milk cow. 1. Nitrogen digestibility and utilization of urea for bacterial protein synthesis in the rumen]. |
| PubMed:[Amino acid composition of the fecal bacteria in the pig]. |
| PubMed:Colicin M is an inhibitor of murein biosynthesis. |
| PubMed:Structure-activity studies on an excitatory receptor for glutamate on leech Retzius neurones. |
| PubMed:[Difference of uptake of 2,6-diamino (G-3H) pimelic acid dihydrochloride among Mycobacterium, Rhodococcus, and Nocardia (author's transl)]. |
| PubMed:Synthesis of pimeloyl coenzyme A. |
| PubMed:Pattern of aliphatic dicarboxylic acids in uremic serum including a new organic acid, 2,4-dimethyladipic acid. |
| PubMed:Action of 5-(2-thienyl)valeric acid as a biotin antagonist. |
| PubMed:Rat urinary metabolites of [9,10-methylene-14C] sterculic acid. |
| PubMed:Anaerobic degradation of benzoate to methane by a microbial consortium. |
| PubMed:Glucosamine-labelled envelope proteins of Escherichia coli K-12. I. Electrophoretic studies and partial fractionation of phenol-soluble proteins. |
| PubMed:Physiological function of the Pseudomonas putida PpG6 (Pseudomonas oleovorans) alkane hydroxylase: monoterminal oxidation of alkanes and fatty acids. |
| PubMed:The antagonist effect of alpha-amino-pimelic acid on glutamate-induced inhibitions of Helix neurones. |
| PubMed:Biological studies of amiclenomycin. |
| PubMed:Growth of a wild strain and of a pimelic acid-utilizing mutant of Pseudomonas azelaica on aliphatic dicarboxylic acids. |
| PubMed:The direction of glycan synthesis in a bacterial peptidoglycan. |
| PubMed:Synthesis of biotin-vitamers from pimelic acid and coenzyme A by cell-free extracts of various bacteria. |
| PubMed:Two new antimetabolites of biotin: alpha-methyldethiobiotin and alpha-methylbiotin. |
| PubMed:Biological studies with alpha-dehydrobiotin. |
| PubMed:[The antimicrobial properties of some derivatives of pimelic acid and nitrobenzene]. |
| PubMed:Uptake of pimelic acid by Escherichia coli and Pseudomonas denitrificans. |
| PubMed:Synthesis of desthiobiotin from 7,8-diaminopelargonic acid in biotin auxotrophs of Escherichia coli K-12. |
| PubMed:Synthesis of 7-oxo-8-aminopelargonic acid, a biotin vitamer, in cell-free extracts of Escherichia coli biotin auxotrophs. |
| PubMed:An early intermediate in the biosynthesis of biotin: Incorporation studies with [1,7-C(2)]pimelic acid. |
| PubMed:The biosynthesis of biotin in growing yeast cells: The formation of biotin from an early intermediate. |
| PubMed:PURIFICATION AND PROPERTIES OF DIAMINOPIMELATE DECARBOXYLASE FROM ESCHERICHIA COLI. |
| PubMed:INTERACTION OF ASPARTATE AMINOTRANSFERASE WITH AMINO ACIDS. |
| PubMed:[A THIN-LAYER CHROMATOGRAPHIC METHOD FOR THE QUANTITATIVE DETERMINATION OF AMINO ACIDS AND AMINOSUGARS IN MICROMEASURES]. |
| PubMed:EXTENT OF CROSS LINKAGE IN THE MUREIN SACCULUS OF ESCHERICHIA COLI B CELL WALL. |
| PubMed:CHEMICAL COMPOSITION OF CELL-WALL PREPARATIONS FROM STRAINS OF VARIOUS FORM-GENERA OF AEROBIC ACTINOMYCETES. |
| PubMed:[ETHYLENE GLYCOL-GAMMA-KETOPIMELATE POLYESTER AS THE FLUID PHASE IN GAS-LIQUID-DISTRIBUTION CHROMATOGRAPHY]. |
| PubMed:AMINO ACIDS OF COLON AND RECTUM. POSSIBLE INVOLVEMENT OF DIAMINOPIMELIC ACID OF INTESTINAL BACTERIA IN ANTIGENICITY OF ULCERATIVE COLITIS COLON. |
| PubMed:[ON THE MECHANISM OF ACTION OF PENICILLIN. I. ISOLATION AND CHARACTERIZATION OF PEPTIDES CONTAINING LOW MOLECULAR 2,6-DIAMINOPIMELIC ACID FROM PENICILLIN SPHEROPLASTS OF ESCHERICHIA COLI B]. |
| PubMed:[STEREOSPECIFIC SYNTHESIS OF A MONO-N-ACYLATED DERIVATIVE OF ALPHS-MESO, ALPHA'-DIAMINOPIMELIC ACID]. |
| PubMed:DEPENDENCE OF THE CONTENT OF CELL ENVELOPES ON THE GROWTH RATE OF BACILLUS MEGATERIUM. |
| PubMed:PIMELIC ACID AS A BY-PRODUCT OF AZELAIC ACID DEGRADATION BY PSEUDOMONAS SP. |
| PubMed:D-ORNITHINE AS A CONSTITUENT OF A BACTERIAL CELL WALL. |
| PubMed:BIOSYNTHESIS OF DIPICOLINIC ACID AND OF LYSINE IN PENICILLIUM CITREO-VIRIDE. |
| PubMed:ON THE "ACTIVATION" OF MESO-ALPHA,EPSILON-DIAMINOPIMELIC ACID BY ESCHERICHIA COLI. |
| PubMed:[DEMONSTRATION OF THE CONSTITUENTS OF THE MUCOPEPTIDE OF THE BACTERIAL WALL IN A STABLE L FORM]. |
| PubMed:NOTES ON THE PHYLOGENETIC BACKGROUND TO LACTOBACILLUS TAXONOMY. |
| PubMed:EFFECT OF AMINO ACIDS ON UPTAKE OF L-HISTIDINE BY RAT BRAIN SLICES. |
| PubMed:PRODUCTS OF THE OXIDATION OF SELECTED ALKANES BY A GRAM-NEGATIVE BACTERIUM. |
| PubMed:THE BIOTIN ENZYMES. |
| PubMed:DEGRADATION AND TURNOVER OF BACTERIAL CELL WALL MUCOPEPTIDES IN GROWING BACTERIA. |
| PubMed:[BEHAVIOR OF MESO-A,A'-DIAMINOPIMELIC ACID PEPTIDES IN THE COURSE OF THEIR CHROMATOGRAPHY ON PAPER]. |
| PubMed:STUDIES ON THE ACTIONS OF PYRAZOLOPYRIMIDINES IN MICROORGANISMS. II. 4-AMINOPYRAZOLOPYRIMIDINE. |
| PubMed:[STRUCTURE AND METABOLISM OF E. COLI SUPPORTING MEMBRANES]. |
| PubMed:A STUDY OF CELL WALL COMPONENTS OF PLEUROPNEUMONIA-LIKE ORGANISMS. |
| PubMed:[ISOLATION OF PEPTIDO-GLYCOLIPID FRACTIONS FROM WAX D OF BOVINE, ATYPICAL, AVIAN AND SAPROPHYTIC STRAINS OF MYCOBACTERIA]. |
| PubMed:BIOTIN BIOSYNTHESIS. I. BIOTIN YIELDS AND BIOTIN VITAMERS IN CULTURES OF PHYCOMYCES BLAKESLEEANUS. |
| PubMed:[VARIABILITY OF CL. PERFRINGENS. III. COMPARATIVE STUDY OF THE CHARACTERISTIC CHEMICAL CONSTITUENTS OF THE CELL WALL OF THE B.P.6K STRAIN AND THE B.P.6K-P.1000 VARIANT]. |
| PubMed:THE ACCUMULATION OF NUCLEOTIDES BY ESCHERICHIA COLI STRAIN 26-26. |
| PubMed:DIAMINOPIMELIC ACID DECARBOXYLASE OF THE AGENT OF MENINGOPNEUMONITIS. |
| PubMed:[Action of leucine-aminopeptidase on symmetrical peptides of meso-alpha,alpha'-diaminopimelic acid]. |
| PubMed:Ribonucleic acid in a "membrane" fraction of Escherichia coli and its relation to cell-wall synthesis. |
| PubMed:The incorporation of 1,7 C14 pimelic acid into biotin vitamers. |
| PubMed:N-succinyl-L-diamino-pimelic acid, an intermediate in the biosynthesis of diaminopimelic acid. |
| PubMed:[Some derivatives of 4-keto pimelic acid, and their antituberculotic activities]. |
| PubMed:[Pimelic acid and adipic acid derivatives, and their antituberculotic activities]. |
| PubMed:PIMELIC ACID, BIOTIN AND CERTAIN FUNGI. |
| PubMed:THE GROWTH-STIMULATING EFFECT OF BIOTIN FOR THE DIPHTHERIA BACILLUS IN THE ABSENCE OF PIMELIC ACID. |
| PubMed:The water-soluble B-vitamins: Alloxazine-adenine-dinucleotide, adenylic acid, nicotinamide and pimelic acid in the nutrition of the rat. |
| PubMed:Studies on Cultural Requirements of Bacteria: X. Pimelic Acid as a Growth Stimulant for C. diphtheriae. |
| PubMed:PIMELIC ACID AS A GROWTH ACCESSORY FACTOR FOR A STRAIN OF THE DIPHTHERIA BACILLUS. |
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A group of compounds that are derivatives of heptanedioic acid with the general formula R-C7H11O4.
Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one methylene longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides.
Pimelic acid has been synthesized from cyclohexanone and from salicylic acid.[1] In the former route, the additional carbon is suppled by dimethyloxalate, which reacts with the enolate. (Wikipedia) [HMDB]
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3D/inchi