Showing Compound Card for Stearic acid (CDB006151)

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Record Information
Version1.0
Created at2020-03-18 23:21:50 UTC
Updated at2020-12-07 19:06:55 UTC
CannabisDB IDCDB006151
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameStearic 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 ). Stearic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC18H36O2
Average Molecular Weight284.48
Monoisotopic Molecular Weight284.2715
IUPAC Name2,2,5-trimethylhexane
Traditional Name2,2,5-trimethylhexane
CAS Registry Number609343-71-7
SMILES
CCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassAlkanes
Direct ParentBranched alkanes
Alternative ParentsNot Available
Substituents
  • Branched alkane
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

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Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point68.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0006 mg/mLNot Available
logP8.23SANGSTER (1993)
Predicted Properties
PropertyValueSource
logP5.05ALOGPS
logP4.01ChemAxon
logS-4.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.98 m³·mol⁻¹ChemAxon
Polarizability17.71 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,2,5-Trimethylhexane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound19041
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Hunter JE, Zhang J, Kris-Etherton PM: Cardiovascular disease risk of dietary stearic acid compared with trans, other saturated, and unsaturated fatty acids: a systematic review. Am J Clin Nutr. 2010 Jan;91(1):46-63. doi: 10.3945/ajcn.2009.27661. Epub 2009 Nov 25. [PubMed:19939984 ]