U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H36O2
Molecular Weight 284.4772
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Stearic acid

SMILES

CCCCCCCCCCCCCCCCCC(O)=O

InChI

InChIKey=QIQXTHQIDYTFRH-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Stearic Acid is a typical example of a fatty acid, which are essentially long hydrocarbon chains containing a carboxyl group at one end and a methyl group at the other. The chain lengths can vary from 3 (propionic acid) to 24 (lignoceric acid) but the majority of fatty acids found in hydrogenated vegetable or animal oils are around C16-C20 in length. Stearic acid is a saturated acid, since there are no double bonds between neighbouring carbon atoms. Stearic acid is found in various animal and plant fats, and is a major component of cocoa butter and shea butter. Stearic acid is a very common amino acid is used in the manufacturing of more than 3,200 skin and hair care products sold in the United States. On product labels, it is sometimes listed under other names, including Century 1240, cetylacetic acid, Emersol 120, Emersol 132, Emersol 150, Formula 300 and Glycon DP. Stearic Acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products. Stearic acid is used along with castor oil for preparing softeners in textile sizing. Being inexpensively available and chemically benign, stearic acid finds many niche applications It is used in the manufacture of candles, and as a hardener in candies when mixed with simple sugar and corn syrup. It is also used to produce dietary supplements. In fireworks, stearic acid is often used to coat metal powders such as aluminum and iron. This prevents oxidation, allowing compositions to be stored for a longer period of time. Stearic acid is a common lubricant during injection molding and pressing of ceramic powders. It is also used as a mold release for foam latex that is baked in stone molds. Stearic acid is known antidiabetic and antioxidant agent.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
CELLBN First care cleanser

Approved Use

Unknown

Launch Date

1.49575683E12
Preventing
MARY KAY TIMEWISE REPAIR VOLU-FIRM THE GO SET

Approved Use

Uses: helps prevent sunburn if used as directed with other sun protection measures (see Directions), decreases the risk of skin cancer and early skin aging caused by the sun

Launch Date

1.5107904E12
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Characterisation of myogenic cell membrane: II. Dynamic changes in membrane lipids during the differentiation of mouse C2 myoblast cells.
2001
Fatty acid and triglyceride composition of milk fat from lactating Holstein cows in response to supplemental canola oil.
2001 Apr
Biogenic amines in the human neocortex in patients with neocortical and mesial temporal lobe epilepsy: identification with in situ microvoltammetry.
2001 Apr 27
Heterogeneous fatty acylation of Src family kinases with polyunsaturated fatty acids regulates raft localization and signal transduction.
2001 Aug 17
Palmitate decreases proton pumping of liver-type cytochrome c oxidase.
2001 Dec
A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males.
2001 Feb
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.
2001 Jan-Feb
Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate.
2001 Jul
DC calcium lactate, a new filler-binder for direct compaction of tablets.
2001 Jun 19
Effect of polymer molecular weight and addition of calcium stearate on response of MG63 osteoblast-like cells to UHMWPE particles.
2001 Mar
[The firmness of Avicel PH 102 and Avicel PH 301 compression and the effect of magnesium stearate] ].
2001 Mar
Effect of magnesium stearate or calcium stearate as additives on dissolution profiles of diltiazem hydrochloride from press-coated tablets with hydroxypropylmethylcellulose acetate succinate in the outer shell.
2001 Mar 23
Saturated non-esterified fatty acids stimulate de novo diacylglycerol synthesis and protein kinase c activity in cultured aortic smooth muscle cells.
2001 May
Characterization of alpha-phase soft proton-exchanged LiNbO3 optical waveguides.
2001 May
On the difficulty of assessing the specific surface area of magnesium stearate.
2001 May 7
Identification and total synthesis of novel fatty acids from the Siphonarid limpet Siphonaria denticulata.
2001 Nov
Determination of oxamniquine in capsules by HPLC.
2001 Nov
X-ray structure of the orphan nuclear receptor RORbeta ligand-binding domain in the active conformation.
2001 Nov 1
Isofenphos induced metabolic changes in K562 myeloid blast cells.
2001 Oct
Stress relaxation studies of granules as a function of different lubricants.
2001 Sep
The cytotoxicity and chemical constituents of the hexane fraction of Typhonium flagelliforme (Araceace).
2001 Sep
Food-drug interactions.
2002
Molecular species of acylglycerols incorporating radiolabeled fatty acids from castor (Ricinus communis L.) microsomal incubations.
2002 Aug 28
The influence of sterilization method on wear performance of the low contact stress total knee system.
2002 Feb
Studies of rapidly disintegrating tablets in the oral cavity using co-ground mixtures of mannitol with crospovidone.
2002 Feb
[Effect of magnesium stearate on the tensile strength of tablets made with the binder Prosolv SMCC 90].
2002 Jan
Application of fluidized hot-melt granulation (FHMG) for the preparation of granules for tableting; properties of granules and tablets prepared by FHMG.
2002 Jan
The effect of formulation on reduced radioiodide thyroid uptake.
2002 Jan
Compactibility of mixtures of calcium carbonate and microcrystalline cellulose.
2002 Jan 1
Comparison of effects of cholecystokinin and erythromycin on bile chemistry and gallstone formation in aged guinea pigs.
2002 Jan-Feb
3-nitropropionic acid-induced changes in bilayer fluidity in synaptosomal membranes: implications for Huntington's disease.
2002 Jun
The effects of some physico-chemical factors and pharmaceutical excipients on the bioavailability of nitrofurantoin oily and aqueous suspensions in rats.
2002 Mar
Loss of regulation of lipogenesis in the Zucker diabetic rat. II. Changes in stearate and oleate synthesis.
2002 Mar
Effect of nitrosylmyoglobin and saturated fatty acid anions on metmyoglobin-catalyzed oxidation of aqueous methyl linoleate emulsions.
2002 Mar 15
Investigation of excipient type and level on drug release from controlled release tablets containing HPMC.
2002 May
Pancreatic beta-cell alpha2A adrenoceptor and phospholipid changes in hyperlipidemic rats.
2002 May
Fatty acid mobilized by the vascular endothelial growth factor in human endothelial cells.
2002 Nov
Roller compaction and tabletting of St. John's wort plant dry extract using a gap width and force controlled roller compactor. I. Granulation and tabletting of eight different extract batches.
2002 Nov
Formulation and stability evaluation of ketoprofen sustained-release tablets prepared by fluid bed granulation with Carbopol 971P solution.
2002 Nov
Synthesis and selectin-binding activity of N-deacetylsialyl Lewis X ganglioside.
2002 Nov 19
Characterization of a surface modified dry powder inhalation carrier prepared by "particle smoothing".
2002 Oct
Rheological properties of three component creams containing sorbitan monoesters as surfactants.
2002 Oct 24
Mixing of cohesive pharmaceutical formulations in tote (bin) blenders.
2002 Sep
Design of controlled release system with multi-layers of powder.
2002 Sep
Influence of physical parameters and lubricants on the compaction properties of granulated and non-granulated cross-linked high amylose starch.
2002 Sep
Sonolysis of surfactants in aqueous solutions: an accumulation of solute in the interfacial region of the cavitation bubbles.
2002 Sep
Inverse gas chromatography study on partially esterified paper fiber.
2002 Sep 6
Duration of coffee- and exercise-induced changes in the fatty acid profile of human serum.
2003 Feb
Further investigations into the use of high sensitivity differential scanning calorimetry as a means of predicting drug-excipient interactions.
2003 Feb 18
The influence of lipid nanocapsule composition on their size distribution.
2003 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: When these same investigators used a lower amount of dietary stearic acid (i.e., an increase of 3 g/day using milk chocolate) in a similar study, no differences in platelet aggregation or platelet activation activity were found
A stearic acid-rich diet (~ 7% of calories or 19 g/day) had beneficial effects on several measures of thrombosis (e.g., platelet volume, platelet aggregation, coagulation factor VII activity) in healthy males. Stearic acid was increased by 12 g/day using stearic acid-enriched margarine.
Route of Administration: Oral
Inhibition of EDR (endothelium-dependent relaxation) induced by acetylcholine was dose-dependent (0.5-2 mmol/l NEFA), and the greatest inhibition (51%) was observed with stearic acid (2 mmol/l).
Name Type Language
Stearic acid
DSC   EP   FHFI   HSDB   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
PURIFIED STEARIC ACID [NF]
Common Name English
STEARIC ACID [DSC]
Common Name English
STEARIC ACID [USP-RS]
Common Name English
N-OCTADECANOIC ACID
Common Name English
HYDROFOL ACID 150
Common Name English
BAROLUB FTA
Common Name English
STEARIC ACID [FHFI]
Common Name English
STEARIC ACID [MART.]
Common Name English
STEARIC ACID [HSDB]
Common Name English
STEARIC ACID [JAN]
Common Name English
STEARIC ACID [MI]
Common Name English
STEARIC ACID (CONSTITUENT OF EVENING PRIMROSE OIL) [DSC]
Common Name English
STEARIC ACID (CONSTITUENT OF FLAX SEED OIL) [DSC]
Common Name English
STEARIC ACID [VANDF]
Common Name English
NSC-261168
Code English
NSC-25956
Code English
CENTURY 1210
Common Name English
ADEKA SA 300
Common Name English
Stearic acid [WHO-DD]
Common Name English
STEARATE
Common Name English
STEARIC ACID [INCI]
Common Name English
OCTADECANOIC ACID
Systematic Name English
STEARIC ACID [EP MONOGRAPH]
Common Name English
STEARIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
STEARIC ACID [II]
Common Name English
FEMA NO. 3035
Code English
DERVACID 3155
Common Name English
PURIFIED STEARIC ACID
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68388
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
CFR 21 CFR 184.1090
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
JECFA EVALUATION STEARIC ACID
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
CFR 21 CFR 357.210
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
CFR 21 CFR 172.860
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
EPA PESTICIDE CODE 79082
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
NCI_THESAURUS C68421
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
DSLD 7 (Number of products:123)
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
Code System Code Type Description
NSC
261168
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
DRUG CENTRAL
4611
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
CAS
57-11-4
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
MERCK INDEX
m10200
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY Merck Index
NSC
25956
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
NCI_THESAURUS
C68426
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
SMS_ID
100000078760
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
CHEBI
25629
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
HSDB
2000
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
FDA UNII
4ELV7Z65AP
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-313-4
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
CHEBI
28842
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
JECFA MONOGRAPH
1092
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
RXCUI
1310551
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY RxNorm
PUBCHEM
5281
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL46403
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
RXCUI
1368706
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
ALTERNATIVE
EVMPD
SUB12597MIG
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
RS_ITEM_NUM
1621008
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
DAILYMED
4ELV7Z65AP
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
WIKIPEDIA
STEARIC ACID
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
MESH
C031183
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID8021642
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY
DRUG BANK
DB03193
Created by admin on Fri Dec 15 16:19:45 UTC 2023 , Edited by admin on Fri Dec 15 16:19:45 UTC 2023
PRIMARY