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 |
|---|---|---|---|
Target ID: CHEMBL5586 |
9.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 Date1.49575683E12 |
|||
| 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 Date1.5107904E12 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions. | 2000 Jun 20 |
|
| [Atherosclerosis and nutrition]. | 2000 Sep |
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| A comparison of reflectance and transmittance near-infrared spectroscopic techniques in determining drug content in intact tablets. | 2001 |
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| Fatty acid and triglyceride composition of milk fat from lactating Holstein cows in response to supplemental canola oil. | 2001 Apr |
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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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| Palmitate decreases proton pumping of liver-type cytochrome c oxidase. | 2001 Dec |
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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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| DAG accumulation from saturated fatty acids desensitizes insulin stimulation of glucose uptake in muscle cells. | 2001 Feb |
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| Unsaturated fatty acids down-regulate srebp isoforms 1a and 1c by two mechanisms in HEK-293 cells. | 2001 Feb 9 |
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| Effects of lipids and oleic acid on biomass development in anaerobic fixed-bed reactors. Part II: Oleic acid toxicity and biodegradability. | 2001 Jan |
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| Long-term stability characterization of a controlled release gastrointestinal therapeutic system coated with a cellulose acetate pseudolatex. | 2001 Jan |
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| Influence of wet granulation and lubrication on the powder and tableting properties of codried product of microcrystalline cellulose with beta-cyclodextrin. | 2001 Jan |
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| Preparation of platinum nanoparticles by sonochemical reduction of the Pt(IV) ions: role of surfactants. | 2001 Jan |
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| An in vitro investigation of the suitability of press-coated tablets with hydroxypropylmethylcellulose acetate succinate (HPMCAS) and hydrophobic additives in the outer shell for colon targeting. | 2001 Jan 29 |
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| Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation. | 2001 Jan-Feb |
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| Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate. | 2001 Jul |
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| Effect of polymer molecular weight and addition of calcium stearate on response of MG63 osteoblast-like cells to UHMWPE particles. | 2001 Mar |
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| [The firmness of Avicel PH 102 and Avicel PH 301 compression and the effect of magnesium stearate] ]. | 2001 Mar |
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| Formulation and process optimization to eliminate picking from market image tablets. | 2001 Mar 14 |
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| 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 |
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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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| Characterization of alpha-phase soft proton-exchanged LiNbO3 optical waveguides. | 2001 May |
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| On the difficulty of assessing the specific surface area of magnesium stearate. | 2001 May 7 |
|
| Plasma transport and tissue distribution of beta-carotene, vitamin A and retinol-binding protein in domestic cats. | 2001 Nov |
|
| Fatty acid modulation and sequence identity of fetal guinea pig alveolar type II cell amiloride-sensitive Na+ channel. | 2001 Nov 2 |
|
| Stress relaxation studies of granules as a function of different lubricants. | 2001 Sep |
|
| [Extracellular metabolites of hydrocarbon-oxidizing bacteria as a substrate for sulfate reduction]. | 2001 Sep-Oct |
|
| Response surface methodology to obtain naproxen controlled release tablets from its microspheres with Eudragit L100-55. | 2001 Sep-Oct |
|
| Content of retinol and retinyl esters in blood plasma, liver, kidney and reproductive organs of Japanese quails. | 2002 |
|
| Food-drug interactions. | 2002 |
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| Dietary cholesterol modulates delta6 and delta9 desaturase mRNAs and enzymatic activity in rats fed a low-eFA diet. | 2002 Apr |
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| Acute effects of fatty acids on insulin secretion from rat and human islets of Langerhans. | 2002 Apr |
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| Design of Peumus boldus tablets by direct compression using a novel dry plant extract. | 2002 Feb 21 |
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| 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 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 |
|
| 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 |
|
| The apoplastic oxidative burst in response to biotic stress in plants: a three-component system. | 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. I. Granulation and tabletting of eight different extract batches. | 2002 Nov |
|
| Effect of weight loss on insulin sensitivity and intramuscular long-chain fatty acyl-CoAs in morbidly obese subjects. | 2002 Oct |
|
| Mixing of cohesive pharmaceutical formulations in tote (bin) blenders. | 2002 Sep |
|
| Mass spectrometric analysis of GAP-43/neuromodulin reveals the presence of a variety of fatty acylated species. | 2002 Sep 6 |
|
| Further investigations into the use of high sensitivity differential scanning calorimetry as a means of predicting drug-excipient interactions. | 2003 Feb 18 |
|
| Spray-dried chitinosans. Part II: in vitro drug release from tablets made from spray-dried chitinosans. | 2003 Feb 18 |
|
| Chitinosan-drug complexes: effect of electrolyte on naproxen release in vitro. | 2003 Jan 2 |
|
| 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
| Substance Class |
Chemical
Created
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on
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| Record UNII |
4ELV7Z65AP
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Validated (UNII)
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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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| Code System | Code | Type | Description | ||
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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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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 |
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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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
TUNISIAN SOURCE
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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 |
U.S produced rice oil. Values are % of composition.
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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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LIPID -> FATTY ACID |
Values are % of total.
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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 |
MAY BE 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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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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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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SALT/SOLVATE -> PARENT | |||
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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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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 |
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ACTIVE MOIETY |
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