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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-08-17 21:42:19 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameSebacic acid
DescriptionSebacic 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. (PMID: 10556649 , 1738216 , 8442769 , 12706375 ).
1,10-Decanedioic acidChEBI
Decanedioic acidChEBI
1,8-Octanedicarboxylic acidHMDB
4,7-Dioxosebacic acidHMDB
4-Oxodecanedioic acidHMDB
Acide sebaciqueHMDB
Decanedicarboxylic acidHMDB
Dicarboxylic acid C10HMDB
Ipomic acidHMDB
N-Decanedioic acidHMDB
Sebacic acidsHMDB
Seracic acidHMDB
Chemical FormulaC10H18O4
Average Molecular Weight202.2475
Monoisotopic Molecular Weight202.120509064
IUPAC Namedecanedioic acid
Traditional Namesebacic acid
CAS Registry Number111-20-6
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
  • Medium-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting Point130.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.91 mg/mLALOGPS
pKa (Strongest Acidic)4.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity51.14 m3·mol-1ChemAxon
Polarizability22.61 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00mk-2910000000-944d83241331f8be19a6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00mk-1910000000-2e3fc1189a96874a25c9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00fr-9400000000-d288a779699c505fde08View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00pj-3910000000-87feed2c593dbff7fae8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0udi-0290000000-cd204cf662cb75a52f8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0540-5910000000-d9df3022a95972158b37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ue9-9660000000-49a78126c0d15f6e3eb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0090000000-841b953970b4cd52f8beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uei-0950000000-001fe11fe26a2d644897View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-83a69e4c3ab60df51781View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-08i9-7900000000-951787b9bed084d77a6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-057i-9000000000-83b9d67dcdf5f385ab57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f80-0950000000-7fec916790f882e8630aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0532-9200000000-34e843efdffcce316afdView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
  • Not Applicable
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
FecesDetected and Quantified11.0755 +/- 10.235 uMNot SpecifiedNot Specified
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.565 +/- 3.385 umol/mmol creatinineAdult (>18 years old)BothNot Available details
UrineDetected and Quantified0.60 +/- 0.78 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified9.5 +/- 12.8 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.493 +/- 2.271 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    • Mordechai, Hien, ...
UrineDetected and Quantified<9.83 umol/mmol creatinineChildren (1 - 18 years old)Both
    • BC Children's Hos...
UrineDetected and Quantified2.0 - 5.0 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.9 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdult (>18 years old)BothCarnitine-acylcarnitine translocase deficiency details
UrineDetected and Quantified161.5 (57.0-266.0) umol/mmol creatinineChildren (1-13 years old)BothCarnitine-Acylcarnitine translocase deficiency details
UrineDetected and Quantified9.263 +/- 8.411 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
Associated Disorders and Diseases
Disease References
Carnitine-acylcarnitine translocase deficiency
  1. MetaGene [Link]
Associated OMIM IDs
  • 212138 (Carnitine-acylcarnitine translocase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022247
KNApSAcK IDNot Available
Chemspider ID5004
KEGG Compound IDC08277
BioCyc IDCPD-3623
BiGG IDNot Available
Wikipedia LinkSebacic acid
NuGOwiki LinkHMDB00792
Metagene LinkHMDB00792
PubChem Compound5192
ChEBI ID41865
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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [2026685 ]
  2. 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. [6698061 ]
  3. Fleming AB, Saltzman WM: Pharmacokinetics of the carmustine implant. Clin Pharmacokinet. 2002;41(6):403-19. [12074689 ]
  4. 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. [6959231 ]
  5. Bertuzzi A, Finotti E, Mingrone G, Greco AV: Sebacic acid binding to human plasma albumin. Biochem Pharmacol. 1993 Feb 9;45(3):697-702. [8442769 ]
  6. 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. [10556649 ]
  7. 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. [1738216 ]
  8. 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. [12706375 ]