Sebacic acid (CHEM003839)

Record Information
Version1.0
Creation Date2014-09-11 05:20:45 UTC
Update Date2026-05-14 18:43:35 UTC
Accession NumberCHEM003839
Identification
Common NameSebacic acid
ClassSmall Molecule
Description
Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD) or glutaric aciduria type II (GAII) are a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic Acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials. (2, 3, 4, 5).
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Cosmetic Toxin
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plasticizer
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,10-Decanedioic acidChEBI
1,8-DicarboxyoctaneChEBI
Decanedioic acidChEBI
SebacinsaeureChEBI
1,10-DecanedioateGenerator
DecanedioateGenerator
SebacateGenerator
1,8-OctanedicarboxylateHMDB
1,8-Octanedicarboxylic acidHMDB
4,7-Dioxosebacic acidHMDB
4-OxodecanedioateHMDB
4-Oxodecanedioic acidHMDB
Acide sebaciqueHMDB
Decanedicarboxylic acidHMDB
Dicarboxylic acid C10HMDB
Ipomic acidHMDB
N-DecanedioateHMDB
N-Decanedioic acidHMDB
Sebacic acidsHMDB
SebacinsaureHMDB
Seracic acidHMDB
Sebacic acid, aluminum saltHMDB
Sebacic acid, monocadmium saltHMDB
Sebacic acid, sodium saltHMDB
Chemical FormulaC10H18O4
Average Molecular Mass202.248 g/mol
Monoisotopic Mass202.121 g/mol
CAS Registry Number111-20-6
IUPAC Namedecanedioic acid
Traditional Namesebacic acid
SMILESOC(=O)CCCCCCCCC(O)=O
InChI IdentifierInChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)
InChI KeyCXMXRPHRNRROMY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point130.8 °C
Boiling Point294.4°C
Solubility1.0 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP1.93ALOGPS
logP2.27ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity51.14 m³·mol⁻¹ChemAxon
Polarizability22.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB07645
HMDB IDHMDB0000792
FooDB IDFDB022247
Phenol Explorer IDNot Available
KNApSAcK IDC00001202
BiGG IDNot Available
BioCyc IDCPD-3623
METLIN ID4240
PDB IDNot Available
Wikipedia LinkSebacic_acid
Chemspider ID5004
ChEBI ID41865
PubChem Compound ID5192
Kegg Compound IDC08277
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceLi, Aimin; Jiang, Zhenmao; Cai, Jianguo; Zhang, Xiao; Shi, Hongyan; Zhou, Jiayan; Zhang, Quanxing; Long, Chao; Liu, Fuqiang; Chen, Jinlong. Environmental friendly method for producing sebacic acid using anion exchangers and polymer adsorbents. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=9439441
3. Li, Aimin; Jiang, Zhenmao; Cai, Jianguo; Zhang, Xiao; Shi, Hongyan; Zhou, Jiayan; Zhang, Quanxing; Long, Chao; Liu, Fuqiang; Chen, Jinlong. Environmental friendly method for producing sebacic acid using anion exchangers and polymer adsorbents. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.
4. Fleming AB, Saltzman WM: Pharmacokinetics of the carmustine implant. Clin Pharmacokinet. 2002;41(6):403-19.
5. Gregersen N, Kolvraa S, Mortensen PB, Rasmussen K: C6-C10-dicarboxylic aciduria: biochemical considerations in relation to diagnosis of beta-oxidation defects. Scand J Clin Lab Invest Suppl. 1982;161:15-27.
6. Bertuzzi A, Finotti E, Mingrone G, Greco AV: Sebacic acid binding to human plasma albumin. Biochem Pharmacol. 1993 Feb 9;45(3):697-702.
7. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38.
8. Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7.
9. Capristo E, Mingrone G, De Gaetano A, Addolorato G, Greco AV, Gasbarrini G: A new HPLC method for the direct analysis of triglycerides of dicarboxylic acids in biological samples. Clin Chim Acta. 1999 Nov;289(1-2):11-21.
10. Mingrone G, Tacchino RM, Castagneto M, Finotti E, Greco AV: Use of even-numbered carbon atom dicarboxylic salts in parenteral nutrition as fuel substrate. JPEN J Parenter Enteral Nutr. 1992 Jan-Feb;16(1):32-8.
11. Curcoy A, Olsen RK, Ribes A, Trenchs V, Vilaseca MA, Campistol J, Osorio JH, Andresen BS, Gregersen N: Late-onset form of beta-electron transfer flavoprotein deficiency. Mol Genet Metab. 2003 Apr;78(4):247-9.