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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:19:35 UTC
HMDB IDHMDB0000792
Secondary Accession Numbers
  • HMDB00792
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), also known as glutaric aciduria type II (GAII), 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 found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. 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 ).
Structure
Thumb
Synonyms
ValueSource
1,10-Decanedioic acidChEBI
1,8-DicarboxyoctaneChEBI
Decanedioic acidChEBI
SebacinsaeureChEBI
1,10-DecanedioateGenerator
SebacateGenerator
DecanedioateGenerator
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 saltMeSH
Sebacic acid, monocadmium saltMeSH
Sebacic acid, sodium saltMeSH
Chemical FormulaC10H18O4
Average Molecular Weight202.2475
Monoisotopic Molecular Weight202.120509064
IUPAC Namedecanedioic acid
Traditional Namesebacic acid
CAS Registry Number111-20-6
SMILES
OC(=O)CCCCCCCCC(O)=O
InChI Identifier
InChI=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
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
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mLNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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) (Non-derivatized)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
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-2910000000-944d83241331f8be19a6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-1910000000-2e3fc1189a96874a25c9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00fr-9400000000-d288a779699c505fde08View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00pj-3910000000-87feed2c593dbff7fae8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-0d93a938bd873800d5e0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9750000000-c51f62deffa53727f438View 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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-841b953970b4cd52f8beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0uei-0950000000-001fe11fe26a2d644897View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-83a69e4c3ab60df51781View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-08i9-7900000000-951787b9bed084d77a6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-057i-9000000000-83b9d67dcdf5f385ab57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0019-0900000000-e9711749ce4f183c8c63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f80-0950000000-e264d8b786405e562fd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-007d-8900000000-fb7880caeb9e996f8bbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0970000000-b21ac000bbddcd19753bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9l-2910000000-aad49769e8652ff2ea40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rw-9200000000-bab98f63e58992b52316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-f600fa6f22d1c40d97d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2790000000-3f24f2c725d420658a66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-1aa6408615ab7e415691View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0532-9200000000-34e843efdffcce316afdView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected and Quantified11.0755 +/- 10.235 uMNot SpecifiedNot Specified
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified3.565 +/- 3.385 umol/mmol creatinineAdult (>18 years old)BothNot Available details
    UrineDetected and Quantified1-4 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
    UrineDetected and Quantified1.118 +/- 2.795 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified4.472 +/- 3.913 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified9.503 +/- 12.857 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    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 Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified4.493 +/- 2.271 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified<9.83 umol/mmol creatinineChildren (1 - 18 years old)Both
    Normal
      • BC Children's Hos...
    details
    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
    BiofluidStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Bothnon-inflamed (NI) control anaemic details
    FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    UrineDetected and Quantified94 umol/mmol creatinineNewborn (0-30 days old)Not Specified
    Carnitine-acylcarnitine translocase deficiency
    details
    UrineDetected and Quantified57-266 umol/mmol creatinineNewborn (0-30 days old)BothCarnitine-acylcarnitine translocase deficiency details
    UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified50.312 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified275.596 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified527.713 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified3-112 umol/mmol creatinineChildren (1 - 13 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency details
    UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdult (>18 years old)BothCarnitine-acylcarnitine translocase deficiency
      • MetaGene: Metabol...
    details
    UrineDetected and Quantified161.5 (57.0-266.0) umol/mmol creatinineChildren (1-13 years old)BothCarnitine-Acylcarnitine translocase deficiency
      • MetaGene: Metabol...
    details
    UrineDetected and Quantified9.263 +/- 8.411 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    Associated Disorders and Diseases
    Disease References
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
    Carnitine-acylcarnitine translocase deficiency
    1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
    Associated OMIM IDs
    • 212138 (Carnitine-acylcarnitine translocase deficiency)
    • 201450 (Medium Chain Acyl-CoA Dehydrogenase 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
    METLIN ID4240
    PubChem Compound5192
    PDB IDDEC
    ChEBI ID41865
    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.
    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. [PubMed: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. [PubMed:6698061 ]
    3. Fleming AB, Saltzman WM: Pharmacokinetics of the carmustine implant. Clin Pharmacokinet. 2002;41(6):403-19. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:12706375 ]