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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

Molecular Formula C18H36O2
Molecular Weight 284.4772
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

2017
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

2017
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
Prediction of drug content and hardness of intact tablets using artificial neural network and near-infrared spectroscopy.
2001 Aug
Palmitate decreases proton pumping of liver-type cytochrome c oxidase.
2001 Dec
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
Isolation and characterization of the human stearoyl-CoA desaturase gene promoter: requirement of a conserved CCAAT cis-element.
2001 Jul 1
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
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
Plasma transport and tissue distribution of beta-carotene, vitamin A and retinol-binding protein in domestic cats.
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
Influence of adjuvants on the dissolution profile of tablets containing high doses of spray-dried extract of Maytenus ilicifolia.
2001 Sep
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
Response surface methodology to obtain naproxen controlled release tablets from its microspheres with Eudragit L100-55.
2001 Sep-Oct
Manganese absorption and retention in rats is affected by the type of dietary fat.
2001 Summer
Food-drug interactions.
2002
Acute effects of fatty acids on insulin secretion from rat and human islets of Langerhans.
2002 Apr
Long-chain fatty acid uptake and oxidation in the perfused liver of Walker-256 tumour-bearing rats.
2002 Aug
Studies of rapidly disintegrating tablets in the oral cavity using co-ground mixtures of mannitol with crospovidone.
2002 Feb
Design of Peumus boldus tablets by direct compression using a novel dry plant extract.
2002 Feb 21
Computerized posturography with sway frequency analysis: application in occupational and environmental health.
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
Compactibility of mixtures of calcium carbonate and microcrystalline cellulose.
2002 Jan 1
The impact of low levels of amorphous material (<5%) on the blending characteristics of a direct compression formulation.
2002 Jan 14
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
Investigation of excipient type and level on drug release from controlled release tablets containing HPMC.
2002 May
Buccoadhesive erodible disk for treatment of oro-dental infections: design and characterisation.
2002 May 15
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. II. Study of roller compaction variables on granule and tablet properties by a 3(3) factorial design.
2002 Nov
Development of polymer film dosage forms of lidocaine for buccal administration: II. Comparison of preparation methods.
2002 Nov
Synthesis and selectin-binding activity of N-deacetylsialyl Lewis X ganglioside.
2002 Nov 19
Compatibility between active components of a commercial drug.
2002 Oct
Characterization of a surface modified dry powder inhalation carrier prepared by "particle smoothing".
2002 Oct
Effect of weight loss on insulin sensitivity and intramuscular long-chain fatty acyl-CoAs in morbidly obese subjects.
2002 Oct
Fatty acids carried on albumin modulate proximal tubular cell fibronectin production: a role for protein kinase C.
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
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
Distribution of vitamin A-storing lipid droplets in hepatic stellate cells in liver lobules--a comparative study.
2003 Mar
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:19:45 GMT 2023
Edited
by admin
on Fri Dec 15 16:19:45 GMT 2023
Record UNII
4ELV7Z65AP
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
CFR 21 CFR 184.1090
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
JECFA EVALUATION STEARIC ACID
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
CFR 21 CFR 357.210
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
CFR 21 CFR 172.860
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
EPA PESTICIDE CODE 79082
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
NCI_THESAURUS C68421
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
DSLD 7 (Number of products:123)
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
Code System Code Type Description
NSC
261168
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
DRUG CENTRAL
4611
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
CAS
57-11-4
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
MERCK INDEX
m10200
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY Merck Index
NSC
25956
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
NCI_THESAURUS
C68426
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
SMS_ID
100000078760
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
CHEBI
25629
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
HSDB
2000
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
FDA UNII
4ELV7Z65AP
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-313-4
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
CHEBI
28842
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
JECFA MONOGRAPH
1092
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
RXCUI
1310551
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY RxNorm
PUBCHEM
5281
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL46403
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
RXCUI
1368706
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
ALTERNATIVE
EVMPD
SUB12597MIG
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
RS_ITEM_NUM
1621008
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
DAILYMED
4ELV7Z65AP
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
WIKIPEDIA
STEARIC ACID
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
MESH
C031183
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID8021642
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
DRUG BANK
DB03193
Created by admin on Fri Dec 15 16:19:45 GMT 2023 , Edited by admin on Fri Dec 15 16:19:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range) Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Value is fatty acid composition (%) for US corn oil w/std. deviation of 0.25% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value). Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
MAY BE PRESENT
USP
LIPID -> FATTY ACID
TUNISIAN SOURCE
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Value is fatty acid composition (%) for international corn oil w/std. deviation of 0.6% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Value is % of composition. Oleic safflower variety UC-1 cited by Knowles, P, Calif. Agr. 19(12),15(1965), produced 1.5% by composition.
LIPID -> FATTY ACID
Value is % of total fatty acids. Maiti, S, et al; Handbook of Annual Oilseed Crops, OIBH, New Delhi, India(1988), pp.1987-90
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY