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
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)
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5586 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28450226 |
9.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | CELLBN First care cleanser Approved UseUnknown Launch Date2017 |
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Preventing | MARY KAY TIMEWISE REPAIR VOLU-FIRM THE GO SET Approved UseUses:
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 Date2017 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no |
PubMed
Title | Date | PubMed |
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Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999 Jul 14 |
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Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions. | 2000 Jun 20 |
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Final report on the safety assessment of PEG-25 propylene glycol stearate, PEG-75 propylene glycol stearate, PEG-120 propylene glycol stearate, PEG-10 propylene glycol, PEG-8 propylene glycol cocoate, and PEG-55 propylene glycol oleate. | 2001 |
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Biogenic amines in the human neocortex in patients with neocortical and mesial temporal lobe epilepsy: identification with in situ microvoltammetry. | 2001 Apr 27 |
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A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. | 2001 Feb |
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Effect of cholesterol on miscibility and phase behavior in binary mixtures with synthetic ceramide 2 and octadecanoic acid. Infrared studies. | 2001 Jun 6 |
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Saturated non-esterified fatty acids stimulate de novo diacylglycerol synthesis and protein kinase c activity in cultured aortic smooth muscle cells. | 2001 May |
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Plasma transport and tissue distribution of beta-carotene, vitamin A and retinol-binding protein in domestic cats. | 2001 Nov |
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X-ray structure of the orphan nuclear receptor RORbeta ligand-binding domain in the active conformation. | 2001 Nov 1 |
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Stress relaxation studies of granules as a function of different lubricants. | 2001 Sep |
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The cytotoxicity and chemical constituents of the hexane fraction of Typhonium flagelliforme (Araceace). | 2001 Sep |
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Content of retinol and retinyl esters in blood plasma, liver, kidney and reproductive organs of Japanese quails. | 2002 |
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Food-drug interactions. | 2002 |
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A case of rhinolithiasis in botswana: a mineralogical, microscopic and chemical study. | 2002 Dec |
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Geoglobus ahangari gen. nov., sp. nov., a novel hyperthermophilic archaeon capable of oxidizing organic acids and growing autotrophically on hydrogen with Fe(III) serving as the sole electron acceptor. | 2002 May |
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Development of polymer film dosage forms of lidocaine for buccal administration: II. Comparison of preparation methods. | 2002 Nov |
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Molecular species of PC and PE formed during castor oil biosynthesis. | 2002 Oct |
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Characterization of a surface modified dry powder inhalation carrier prepared by "particle smoothing". | 2002 Oct |
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Rheological properties of three component creams containing sorbitan monoesters as surfactants. | 2002 Oct 24 |
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Mixing of cohesive pharmaceutical formulations in tote (bin) blenders. | 2002 Sep |
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Sonolysis of surfactants in aqueous solutions: an accumulation of solute in the interfacial region of the cavitation bubbles. | 2002 Sep |
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Inverse gas chromatography study on partially esterified paper fiber. | 2002 Sep 6 |
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Duration of coffee- and exercise-induced changes in the fatty acid profile of human serum. | 2003 Feb |
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Chitinosan-drug complexes: effect of electrolyte on naproxen release in vitro. | 2003 Jan 2 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16524362
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
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Record UNII |
4ELV7Z65AP
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Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68388
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CFR |
21 CFR 184.1090
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JECFA EVALUATION |
STEARIC ACID
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CFR |
21 CFR 357.210
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CFR |
21 CFR 172.860
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EPA PESTICIDE CODE |
79082
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NCI_THESAURUS |
C68421
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DSLD |
7 (Number of products:123)
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261168
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4611
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57-11-4
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m10200
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25956
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C68426
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100000078760
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25629
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2000
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4ELV7Z65AP
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200-313-4
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28842
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1310551
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5281
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CHEMBL46403
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1368706
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SUB12597MIG
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1621008
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4ELV7Z65AP
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STEARIC ACID
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C031183
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DTXSID8021642
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DB03193
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID |
U.S produced rice oil. Values are % of composition.
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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)
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Values given are in undefined precent.
Average is typical for U.S. Sunflower oil.
|
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SALT/SOLVATE -> PARENT | |||
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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)
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID |
Values are % of total.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Values are % of total.
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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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)
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LIPID -> FATTY ACID |
JB Rossell and co-workers; JAOCS62(2), 221-230(1985).
Range weight is a mean.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
MAY BE PRESENT
USP
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LIPID -> FATTY ACID |
TUNISIAN SOURCE
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT |
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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)
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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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.
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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
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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