ARACHIDIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H40O2
Molecular Weight	312.5304
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCCCCCCCC(O)=O

InChI

InChIKey=VKOBVWXKNCXXDE-UHFFFAOYSA-N

InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22)

HIDE SMILES / InChI

Molecular Formula	C20H40O2
Molecular Weight	312.5304
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17459764 | https://www.ncbi.nlm.nih.gov/pubmed/28690628

Arachidic acid, also known as eicosanoic, is a component of wild soybean. It is a saturated fatty acid, which is used for the production of detergents and lubricants, and was discovered to modulate expression of cyclooxygenase-2, an enzyme pivotal to skin inflammation and reparation.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Distinct structural elements dictate the specificity of the type III pentaketide synthase from Neurospora crassa.	2008-10-20	18940668
Depth resolution during C60+ profiling of multilayer molecular films.	2008-10-01	18778034
Characterization of domain growth kinetics in a mixed perfluorocarbon-hydrocarbon Langmuir-Blodgett monolayer.	2008-09-01	18597763
Application of a pnCCD in X-ray diffraction: a three-dimensional X-ray detector.	2008-09	18728315
Characterization of Langmuir-Blodgett film using differential charging in X-ray photoelectron spectroscopy.	2008-07-24	18582103
Unsaturated long-chain fatty acids induce the respiratory burst of human neutrophils and monocytes in whole blood.	2008-07-14	18625045
Habitual fish consumption does not prevent a decrease in LCPUFA status in pregnant women (the Seychelles Child Development Nutrition Study).	2008-06	18585023
Physico-chemical behaviour of the fish lipid from Lepidocephalus guntea (Hamilton) and variation of lipid profile with size.	2008-05-15	18817266
Dicyanopyrazine-linked porphyrin Langmuir-Blodgett films.	2008-04-15	18262539
Conversion of the aggregation state of merocyanine dye, modification of the subcell packing of arachidic acid, and removal of the majority of n-octadecane by hydrothermal treatment in the liquid phase in a mixed Langmuir-Blodgett film of the ternary system.	2008-04-01	18288876
Orange-red luminescence from Cu doped CdS nanophosphor prepared using mixed Langmuir-Blodgett multilayers.	2008-03-21	18361597
Hypocholesterolemic effects of fatty acid bile acid conjugates (FABACs) in mice.	2008-03-01	18167305
Study of assembly of arachidic acid/LDHs hybrid films containing photoactive dyes.	2008-02-15	18036601
[Spectrum properties of Thulium bisphthalocyanine Langmuir-Blodgett films].	2008-02	18479037
Chemically alternating Langmuir-Blodgett thin films as a model for molecular depth profiling by mass spectrometry.	2008-01	18293488
Two-component hydrogels comprising fatty acids and amines: structure, properties, and application as a template for the synthesis of metal nanoparticles.	2008	18537217
The roles of long-chain polyunsaturated fatty acids in pregnancy, lactation and infancy: review of current knowledge and consensus recommendations.	2008	18184094
Lipophilic components of different therapeutic mud species.	2007-12	18166123
Fasting nonesterified fatty acid profiles in childhood and their relationship with adiposity, insulin sensitivity, and lipid levels.	2007-12	18055661
Interrelated influence of superoxides and free fatty acids over mitochondrial uncoupling in skeletal muscle.	2007-11-15	18471434
Mechanistic insight into domain formation and growth in a phase-separated Langmuir-Blodgett monolayer.	2007-09-25	17727296
Molecular dynamic simulations of eicosanoic acid and 18-methyleicosanoic acid langmuir monolayers.	2007-09-20	17718471
[A new chemical component of Pueraria lobata (Willd.) Ohwi].	2007-09	18050739
Relationship between serum concentrations of saturated fatty acids and unsaturated fatty acids and the homeostasis model insulin resistance index in Japanese patients with type 2 diabetes mellitus.	2007-08	17878672
Interaction of different metal ions with carboxylic acid group: a quantitative study.	2007-07-19	17585841
Crystallization of silver carboxylates from sodium carboxylate mixtures.	2007-07-17	17567157
Thermal behavior of J-aggregates in mixed Langmuir-Blodgett films composed of merocyanine dye and deuterated arachidic acid investigated by UV-visible and infrared absorption spectroscopy.	2007-06-19	17530788
n-3 and n-6 polyunsaturated fatty acids induce the expression of COX-2 via PPARgamma activation in human keratinocyte HaCaT cells.	2007-05	17459764
DNA microarray data integration by ortholog gene analysis reveals potential molecular mechanisms of estrogen-dependent growth of human uterine fibroids.	2007-04-02	17407572
[Determination of underivatized long-chain fatty acids in edible oils by fast gas chromatography].	2007-03	17580699
Thermodynamic and spectroscopic studies on the nickel arachidate-RNA polymerase Langmuir-Blodgett monolayer.	2007-02-13	17279692
Ordering by collapse: formation of bilayer and trilayer crystals by folding Langmuir monolayers.	2007-02-13	17279671
Docosahexaenoic acid stabilizes soluble amyloid-beta protofibrils and sustains amyloid-beta-induced neurotoxicity in vitro.	2007-02	17227385
Effects of polyunsaturated fatty acids on calcium response and degranulation from RBL-2H3 cells.	2007-02	17178388
Preparative isolation and purification of chemical constituents from the root of Adenophora tetraphlla by high-speed counter-current chromatography with evaporative light scattering detection.	2007-01-19	17150224
Organosilicon-containing thiazole derivatives as potential lipoxygenase inhibitors and anti-inflammatory agents.	2007	18256725
Examining the collision-induced decomposition spectra of ammoniated triglycerides. III. The linoleate and arachidonate series.	2007	17893948
Polymer-surfactant layered heterostructures by electropolymerization of phenosafranine in Langmuir-Blodgett films.	2006-12-07	17134212
Modulation of ATP-induced inward currents by docosahexaenoic acid and other fatty acids in rat nodose ganglion neurons.	2006-11	17099292
[Determination of fatty acids and organic acids in Ranunculus ternatus Thunb using GC-MS].	2006-08	17058970
Phospholipase A2 activity in platelets of patients with primary thrombocythemia.	2006-08	16928606
The venomous secrets of the web droplets from the viscid spiral of the orb-weaver spider Nephila clavipes (Araneae, Tetragnatidae).	2006-07	17193305
Cyclooxygenase inhibitors not inhibit resting lung cancer A549 cell proliferation.	2006-05	16618538
Ethane-bridged zinc porphyrin dimers in Langmuir-Shäfer thin films: structural and spectroscopic properties.	2006-03-16	16526704
Simultaneous determination of saponins and fatty acids in Ziziphus jujuba (Suanzaoren) by high performance liquid chromatography-evaporative light scattering detection and pressurized liquid extraction.	2006-03-10	16458908
Sum-frequency spectroscopy of a monolayer of zinc arachidate at the solid-solid interface.	2006-02-09	16471815
Biochemical and morphological changes in endothelial cells in response to hypoxic interstitial edema.	2006-01-13	16412226
Sum frequency generation from Langmuir-Blodgett multilayer films on metal and dielectric substrates.	2005-10-13	16853409
Formation of a DNA layer on Langmuir-Blodgett films and its enzymatic digestion.	2004-07-06	16459606
Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids.	2003-05	17156034

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The PLA2 activator, melittin (1 microM), enhanced the evoked tritium release by 98+/-11%, an effect prevented by the PLA2 inhibitor, arachidonyl trifluromethylketone (AACOCF3, 20 microM), and by BSA (1%). arachidonic acid (AA) (30 microM), but not arachidic acid (30 microM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:53:14 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:14 GMT 2025`
Record UNII	PQB8MJD4RB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-93983

Preferred Name

English

ARACHIDIC ACID

Official Name

English

ICOSANOIC ACID

Systematic Name

English

EICOSANOIC ACID

Systematic Name

English

ARACHIC ACID

Systematic Name

English

ARACHIDIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]

Common Name

English

N-EICOSANOIC ACID

Common Name

English

EICOSATRIENOIC-ACID

Systematic Name

English

ARACHIDIC ACID [MI]

Common Name

English

ARACHIDATE

Common Name

English

Classification Tree Code System Code

LOINC

35169-2