Stearic acid

Identification

Summary

Stearic acid is an ingredient found in topical products as a skin protectant.

Generic Name
Stearic acid
DrugBank Accession Number
DB03193
Background

Stearic acid (IUPAC systematic name: octadecanoic acid) is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. It is a waxy solid.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Weight
Average: 284.4772
Monoisotopic: 284.271530396
Chemical Formula
C18H36O2
Synonyms
  • Acide octadécanoïque
  • Acide stéarique
  • C18:0
  • n-octadecanoic acid
  • Octadecanoic acid
  • Octadecansäure
  • Octadecoic acid
  • Oktadekansäure
  • Stearic acid
  • Stearinsäure
External IDs
  • Caswell No. 801D
  • FEMA No. 3035
  • NSC-25956
  • NSC-261168

Pharmacology

Indication

Not Available

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Associated Therapies
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeroxisome proliferator-activated receptor alphaNot AvailableHumans
UGroup IID secretory phospholipase A2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Acute oral toxicity (LD50): 4640 mg/kg [Rat]. Acute dermal toxicity (LD50): >5000 mg/kg Rabbit.

Pathways
PathwayCategory
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsMetabolic
Plasmalogen SynthesisMetabolic
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cellbn First Care CleanserCream16 g/100mLTopicalWorldcostec.co.,ltd2017-05-26Not applicableUS flag
Doctor PlusCream1.5 g/100mLTopicalPowerful X2018-01-09Not applicableUS flag
Dr. G Pore Deep Clearing FoamCream15 g/10mLTopicalGOWOONSESANG COSMETICS CO., LTD.2016-03-012018-01-09US flag
Dr.g A-clear FoamCream20 g/100mLTopicalGOWOONSESANG COSMETICS CO., LTD.2015-07-052018-03-23US flag
Dr.g Hyper Brightening Cleansing FoamCream8 g/100mLTopicalGOWOONSESANG COSMETICS CO., LTD.2015-07-052018-01-09US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
For SopeStearic acid (1.5 %) + Sodium lauryl sulfate (97 %)LiquidTopicalRougier Pharma Division Of Ratiopharm Inc1960-12-311999-09-27Canada flag
Huile D'onagre Vitamin EStearic acid (1 %) + Linoleic acid (72 %) + Oleic Acid (9 %) + Palmitic Acid (7 %) + Vitamin E (15 %) + alpha-Linolenic acid (11 %)CapsuleOralLe Naturiste J.M.B. Inc.1987-12-312000-08-23Canada flag
Isa Knox Ageless Serum Makeup Base 10Stearic acid (0.18 mL/100mL) + Aluminum hydroxide (0.18 mL/100mL) + Dimethicone (0.08 mL/100mL) + Hydroxyproline (0.53 mL/100mL) + Octinoxate (3 mL/100mL) + Titanium dioxide (3.38 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-07-04Not applicableUS flag
Isaknox Ageless Serum Moist Pearl BaseStearic acid (0.18 mL/100mL) + Aluminum hydroxide (0.18 mL/100mL) + Dimethicone (0.08 mL/100mL) + Hydroxyproline (0.53 mL/100mL) + Octinoxate (3 mL/100mL) + Titanium dioxide (3.38 mL/100mL)LiquidTopicalLg Household & Health Care Ltd.2010-08-31Not applicableUS flag
Jayjun Anti Dust Fresh Foam CleanserStearic acid (6.84 g/90mL) + Lauric acid (6.30 g/90mL) + Palmitic Acid (11.16 g/90mL)LiquidTopicalJayjun Cosmetic Co.,ltd.2018-12-012019-11-01US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Cellbn First Care CleanserStearic acid (16 g/100mL)CreamTopicalWorldcostec.co.,ltd2017-05-26Not applicableUS flag
Doctor PlusStearic acid (1.5 g/100mL)CreamTopicalPowerful X2018-01-09Not applicableUS flag
Dr. G Pore Deep Clearing FoamStearic acid (15 g/10mL)CreamTopicalGOWOONSESANG COSMETICS CO., LTD.2016-03-012018-01-09US flag
Dr.g A-clear FoamStearic acid (20 g/100mL)CreamTopicalGOWOONSESANG COSMETICS CO., LTD.2015-07-052018-03-23US flag
Dr.g Hyper Brightening Cleansing FoamStearic acid (8 g/100mL)CreamTopicalGOWOONSESANG COSMETICS CO., LTD.2015-07-052018-01-09US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Long-chain fatty acids
Alternative Parents
Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Long-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
long-chain fatty acid, saturated fatty acid, straight-chain saturated fatty acid (CHEBI:28842) / Straight chain fatty acids, Saturated fatty acids (C01530) / Straight chain fatty acids (LMFA01010018)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
4ELV7Z65AP
CAS number
57-11-4
InChI Key
QIQXTHQIDYTFRH-UHFFFAOYSA-N
InChI
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)
IUPAC Name
octadecanoic acid
SMILES
CCCCCCCCCCCCCCCCCC(O)=O

References

Synthesis Reference

Arnold W. Fogel, "12-hydroxy stearic acid esters, compositions based upon same and methods of using and making such compositions." U.S. Patent US5993861, issued July, 1998.

US5993861
General References
Not Available
Human Metabolome Database
HMDB0000827
KEGG Drug
D00119
KEGG Compound
C01530
PubChem Compound
5281
PubChem Substance
46508522
ChemSpider
5091
BindingDB
50240485
RxNav
1310551
ChEBI
28842
ChEMBL
CHEMBL46403
ZINC
ZINC000004978673
PDBe Ligand
STE
Wikipedia
Stearic_acid
PDB Entries
1e7i / 1fk4 / 1hmt / 1k4w / 1lif / 1uvc / 1xxs / 2fva / 2wh5 / 2zyi
show 72 more
MSDS
Download (73.6 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamTopical16 g/100mL
CreamTopical15 g/10mL
CreamTopical20 g/100mL
CreamTopical8 g/100mL
CreamTopical25 g/100mL
CapsuleOral
LiquidTopical
Injectable foamTopical
SoapTopical120 mg/1g
SoapTopical12 g/100g
CreamTopical1 g/100mL
CreamTopical1.5 g/100mL
OintmentTopical
CreamTopical
GelTopical0.4 g/20mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)68.8 °CPhysProp
boiling point (°C)383 °CPhysProp
water solubility0.597 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP8.23SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility6.61e-05 mg/mLALOGPS
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 Å2Chemaxon
Rotatable Bond Count16Chemaxon
Refractivity86.29 m3·mol-1Chemaxon
Polarizability38.64 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9888
Blood Brain Barrier+0.9488
Caco-2 permeable+0.8326
P-glycoprotein substrateNon-substrate0.6321
P-glycoprotein inhibitor INon-inhibitor0.9598
P-glycoprotein inhibitor IINon-inhibitor0.9277
Renal organic cation transporterNon-inhibitor0.9266
CYP450 2C9 substrateNon-substrate0.7886
CYP450 2D6 substrateNon-substrate0.8956
CYP450 3A4 substrateNon-substrate0.6982
CYP450 1A2 substrateInhibitor0.8326
CYP450 2C9 inhibitorNon-inhibitor0.8808
CYP450 2D6 inhibitorNon-inhibitor0.9554
CYP450 2C19 inhibitorNon-inhibitor0.9578
CYP450 3A4 inhibitorNon-inhibitor0.9484
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9647
Ames testNon AMES toxic0.9865
CarcinogenicityNon-carcinogens0.6452
BiodegradationReady biodegradable0.8795
Rat acute toxicity1.3275 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9322
hERG inhibition (predictor II)Non-inhibitor0.8868
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-0159-1900000000-9cc966384906cd35537d
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0159-0900000000-b87a9955374d11966ba6
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-0100-9700000000-979da356343fa0697993
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0159-2901000000-16194c704b7abd193647
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9540000000-c6c002443ac3a40dabdb
GC-MS Spectrum - EI-BGC-MSsplash10-06yo-9110000000-6f345827577cdc861aca
GC-MS Spectrum - EI-BGC-MSsplash10-075c-9220000000-207b53a511763954eb66
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-1900000000-9cc966384906cd35537d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-0900000000-b87a9955374d11966ba6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0100-9700000000-979da356343fa0697993
GC-MS Spectrum - GC-MSGC-MSsplash10-0159-2901000000-16194c704b7abd193647
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1900000000-d34fc01a79cc27a32080
Mass Spectrum (Electron Ionization)MSsplash10-0c03-9200000000-5dd52f837d56d80fa968
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-001i-0090000000-1368043827a20e28c172
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-001i-0090000000-5c3fa1d38cf3d0a38d74
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-004r-0791000000-10ab351997f48e512657
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-004r-0791000000-10ab351997f48e512657
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-004r-0791000000-10ab351997f48e512657
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-001i-0090000000-55efcdc9c7bfd521ef5a
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-001i-0090000000-9441e6362046ae198384
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-001i-0090000000-f629b105972a0728beb6
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-001i-0090000000-fbf3f8e91badb0ec251d
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-001i-0090000000-55efcdc9c7bfd521ef5a
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-00lr-0090000000-a702a9f469dbb513856a
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0090000000-9441e6362046ae198384
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0090000000-fbf3f8e91badb0ec251d
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0090000000-55efcdc9c7bfd521ef5a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014s-4290000000-b37d2fc74ef74ba3031b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-b007baba66b68814e11f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-45d0a556f8c05c399a71
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9510000000-8e5f2390924807c37912
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9420000000-49cd398bbefc0f38ab46
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-ab4c60e319c4535db81e
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.6826617
predicted
DarkChem Lite v0.1.0
[M-H]-176.5943516
predicted
DarkChem Standard v0.1.0
[M-H]-206.7843617
predicted
DarkChem Lite v0.1.0
[M-H]-206.1106617
predicted
DarkChem Lite v0.1.0
[M-H]-170.31721
predicted
DeepCCS 1.0 (2019)
[M+H]+174.33687
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.43562
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Murakami K, Ide T, Suzuki M, Mochizuki T, Kadowaki T: Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. Biochem Biophys Res Commun. 1999 Jul 14;260(3):609-13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase a2 activity
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other...
Gene Name
PLA2G2D
Uniprot ID
Q9UNK4
Uniprot Name
Group IID secretory phospholipase A2
Molecular Weight
16546.1 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Oleic acid binding
Specific Function
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters.
Gene Name
FABP3
Uniprot ID
P05413
Uniprot Name
Fatty acid-binding protein, heart
Molecular Weight
14857.93 Da
References
  1. Fournier NC, Rahim M: Control of energy production in the heart: a new function for fatty acid binding protein. Biochemistry. 1985 Apr 23;24(9):2387-96. doi: 10.1021/bi00330a039. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Spector AA, John K, Fletcher JE: Binding of long-chain fatty acids to bovine serum albumin. J Lipid Res. 1969 Jan;10(1):56-67. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 28, 2021 21:54