Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2020-09-17 15:42:17 UTC
Primary IDFDB002941
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOctadecanoic acid
DescriptionStearic acid, also known as stearate or octadecanoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a waxy solid and is one of the most common saturated fatty acids found in nature (being a close second to palmitic acid). The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is obtained from fats and oils by the saponification of the triglycerides, like stearin, using hot water. Stearic acid exists in all living organisms, ranging from bacteria to humans. Stearic acid has been detected, but not quantified in, several different foods, such as sweet bay, rose hips, muscadine grapes, pummelo, and garland chrysanthemums. Fats and oils rich in stearic acid are more abundant in animal fat (up to 30%) than in vegetable fat (typically <5%). The important exceptions are the foods cocoa butter and shea butter, where the stearic acid content (as a triglyceride) is 28–45%. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks. Stearic acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products. Fatty acids are classic components of candle-making. Stearic acid is used along with simple sugar or corn syrup as a hardener in candies. In epidemiologic and clinical studies, stearic acid was found to be associated with lowered LDL cholesterol in comparison with other saturated fatty acids (PMID:19939984).
CAS Number57-11-4
Structure
Thumb
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.6e-05 g/LALOGPS
logP8.02ALOGPS
logP7.15ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity86.29 m³·mol⁻¹ChemAxon
Polarizability38.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H36O2
IUPAC nameoctadecanoic acid
InChI IdentifierInChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
InChI KeyQIQXTHQIDYTFRH-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCCC(O)=O
Average Molecular Weight284.4772
Monoisotopic Molecular Weight284.271530396
Classification
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 76.00%; H 12.75%; O 11.25%DFC
Melting PointMp 69.7°DFC
Boiling PointBp5 213°DFC
Experimental Water Solubility0.000597 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP8.23SANGSTER (1993)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0c03-9200000000-5dd52f837d56d80fa9682014-09-20View Spectrum
GC-MSOctadecanoic acid, 1 TMS, GC-MS Spectrumsplash10-0159-1900000000-9cc966384906cd35537dSpectrum
GC-MSOctadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0900000000-b87a9955374d11966ba6Spectrum
GC-MSOctadecanoic acid, 1 TMS, GC-MS Spectrumsplash10-0100-9700000000-979da356343fa0697993Spectrum
GC-MSOctadecanoic acid, 1 TMS, GC-MS Spectrumsplash10-0159-2901000000-16194c704b7abd193647Spectrum
GC-MSOctadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-06yo-9110000000-6f345827577cdc861acaSpectrum
GC-MSOctadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-075c-9220000000-207b53a511763954eb66Spectrum
GC-MSOctadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-1900000000-9cc966384906cd35537dSpectrum
GC-MSOctadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0900000000-b87a9955374d11966ba6Spectrum
GC-MSOctadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0100-9700000000-979da356343fa0697993Spectrum
GC-MSOctadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2901000000-16194c704b7abd193647Spectrum
GC-MSOctadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-d34fc01a79cc27a32080Spectrum
Predicted GC-MSOctadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9540000000-c6c002443ac3a40dabdbSpectrum
Predicted GC-MSOctadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009l-9551000000-b9a196da32e6273fad4fSpectrum
Predicted GC-MSOctadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOctadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSOctadecanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-001i-0090000000-1368043827a20e28c1722012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-0090000000-5c3fa1d38cf3d0a38d742012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004r-0791000000-10ab351997f48e5126572017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004r-0791000000-10ab351997f48e5126572017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004r-0791000000-10ab351997f48e5126572017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5a2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-9441e6362046ae1983842017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-f629b105972a0728beb62017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-fbf3f8e91badb0ec251d2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-55efcdc9c7bfd521ef5a2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-00lr-0090000000-a702a9f469dbb513856a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-9441e6362046ae1983842017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-fbf3f8e91badb0ec251d2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0090000000-34a309d09cb2def46a192015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-4690000000-f68e827f7ebccd80d5bf2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-8920000000-2e865f09d760af582c072015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0090000000-34a309d09cb2def46a192015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-4690000000-f68e827f7ebccd80d5bf2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-8920000000-2e865f09d760af582c072015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-b3ce35f839a30b41c7182015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00m0-1090000000-bbb339a3dbe1b9ba0d542015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-1b84b49819fa37fce1ae2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-b3ce35f839a30b41c7182015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00m0-1090000000-bbb339a3dbe1b9ba0d542015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-1b84b49819fa37fce1ae2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID5091
ChEMBL IDCHEMBL46403
KEGG Compound IDC01530
Pubchem Compound ID5281
Pubchem Substance IDNot Available
ChEBI ID28842
Phenol-Explorer IDNot Available
DrugBank IDDB03193
HMDB IDHMDB00827
CRC / DFC (Dictionary of Food Compounds) IDCPL65-U:CPL65-U
EAFUS ID3541
Dr. Duke IDOCTADECANOIC-ACID|STEARIC-ACID
BIGG ID37799
KNApSAcK IDC00032087
HET IDSTE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1009271
SuperScent IDNot Available
Wikipedia IDStearic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5alpha-reductase inhibitor50781 An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.DUKE
cosmetic64857 The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hypocholesterolemicDUKE
lubricantDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
propecicDUKE
suppositoryDUKE
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Liver carboxylesterase 1CES1P23141
Pancreatic triacylglycerol lipasePNLIPP16233
Hepatic triacylglycerol lipaseLIPCP11150
Inactive pancreatic lipase-related protein 1PNLIPRP1P54315
Patatin-like phospholipase domain-containing protein 3PNPLA3Q9NST1
Gastric triacylglycerol lipaseLIPFP07098
Endothelial lipaseLIPGQ9Y5X9
Pancreatic lipase-related protein 2PNLIPRP2P54317
Lipoprotein lipaseLPLP06858
Patatin-like phospholipase domain-containing protein 4PNPLA4P41247
Patatin-like phospholipase domain-containing protein 2PNPLA2Q96AD5
Pancreatic lipase-related protein 3PNLIPRP3Q17RR3
CholinesteraseBCHEP06276
Carboxylesterase 5ACES5AQ6NT32
60 kDa lysophospholipaseASPGQ86U10
Fatty acid synthaseFASNP49327
Galactoside-binding soluble lectin 13LGALS13Q9UHV8
Eosinophil lysophospholipaseCLCQ05315
Cocaine esteraseCES2O00748
Acylphosphatase-2ACYP2P14621
Acylphosphatase-1ACYP1P07311
AspartoacylaseASPAP45381
Aspartoacylase-2ACY3Q96HD9
Acid ceramidaseASAH1Q13510
Homeodomain-interacting protein kinase 1HIPK1Q86Z02
Peroxisome proliferator-activated receptor gammaPPARGP37231
Long-chain fatty acid transport protein 6SLC27A6Q9Y2P4
Long-chain fatty acid transport protein 3SLC27A3Q5K4L6
Long-chain fatty acid transport protein 4SLC27A4Q6P1M0
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Neuropathy target esterasePNPLA6Q8IY17
Carboxylesterase 3CES3Q6UWW8
S-acyl fatty acid synthase thioesterase, medium chainOLAHQ9NV23
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Pathways
NameSMPDB LinkKEGG Link
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482 Not Available
Plasmalogen SynthesisSMP00479 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.