Common NameDecanedioate
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
Molecular FormulaC10H18O4
Average Mass202.24750
Monoisotopic Mass202.12051
IUPAC Namedecanedioic acid
Traditional NameSebacic acid
CAS Registry Number111-20-6
SMILESO=C([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
CHEBI IDCHEBI:76283
HMDB IDHMDB0000792
StateSolid
Water Solubility9.12e-01 g/l
logP1.93
logS-2.35
pKa (Strongest Acidic)4.72
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area74.6 Ų
Rotatable Bond Count9
Physiological Charge-2
Formal Charge0
Refractivity51.14 m³·mol⁻¹
Polarizability22.61

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