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

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 of ARACHIDIC ACID

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids.
2003 May
Calcium signals activated by arachidonic acid in embryonic chick ciliary ganglion neurons.
2005
Cyanolipid-rich seed oils from Allophylus natalensis and A. dregeanus.
2005 Oct
Sum frequency generation from Langmuir-Blodgett multilayer films on metal and dielectric substrates.
2005 Oct 13
[Determination of fatty acids and organic acids in Ranunculus ternatus Thunb using GC-MS].
2006 Aug
Phospholipase A2 activity in platelets of patients with primary thrombocythemia.
2006 Aug
Polymer-surfactant layered heterostructures by electropolymerization of phenosafranine in Langmuir-Blodgett films.
2006 Dec 7
ELOVL3 is an important component for early onset of lipid recruitment in brown adipose tissue.
2006 Feb 24
Sum-frequency spectroscopy of a monolayer of zinc arachidate at the solid-solid interface.
2006 Feb 9
The venomous secrets of the web droplets from the viscid spiral of the orb-weaver spider Nephila clavipes (Araneae, Tetragnatidae).
2006 Jul
Ethane-bridged zinc porphyrin dimers in Langmuir-Shäfer thin films: structural and spectroscopic properties.
2006 Mar 16
Cyclooxygenase inhibitors not inhibit resting lung cancer A549 cell proliferation.
2006 May
Modulation of ATP-induced inward currents by docosahexaenoic acid and other fatty acids in rat nodose ganglion neurons.
2006 Nov
Organosilicon-containing thiazole derivatives as potential lipoxygenase inhibitors and anti-inflammatory agents.
2007
Examining the collision-induced decomposition spectra of ammoniated triglycerides. III. The linoleate and arachidonate series.
2007
DNA microarray data integration by ortholog gene analysis reveals potential molecular mechanisms of estrogen-dependent growth of human uterine fibroids.
2007 Apr 2
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 Aug
Lipophilic components of different therapeutic mud species.
2007 Dec
Fasting nonesterified fatty acid profiles in childhood and their relationship with adiposity, insulin sensitivity, and lipid levels.
2007 Dec
Docosahexaenoic acid stabilizes soluble amyloid-beta protofibrils and sustains amyloid-beta-induced neurotoxicity in vitro.
2007 Feb
Effects of polyunsaturated fatty acids on calcium response and degranulation from RBL-2H3 cells.
2007 Feb
Thermodynamic and spectroscopic studies on the nickel arachidate-RNA polymerase Langmuir-Blodgett monolayer.
2007 Feb 13
Ordering by collapse: formation of bilayer and trilayer crystals by folding Langmuir monolayers.
2007 Feb 13
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 Jan 19
Crystallization of silver carboxylates from sodium carboxylate mixtures.
2007 Jul 17
Interaction of different metal ions with carboxylic acid group: a quantitative study.
2007 Jul 19
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 Jun 19
[Determination of underivatized long-chain fatty acids in edible oils by fast gas chromatography].
2007 Mar
n-3 and n-6 polyunsaturated fatty acids induce the expression of COX-2 via PPARgamma activation in human keratinocyte HaCaT cells.
2007 May
[A new chemical component of Pueraria lobata (Willd.) Ohwi].
2007 Sep
Molecular dynamic simulations of eicosanoic acid and 18-methyleicosanoic acid langmuir monolayers.
2007 Sep 20
Mechanistic insight into domain formation and growth in a phase-separated Langmuir-Blodgett monolayer.
2007 Sep 25
Two-component hydrogels comprising fatty acids and amines: structure, properties, and application as a template for the synthesis of metal nanoparticles.
2008
The roles of long-chain polyunsaturated fatty acids in pregnancy, lactation and infancy: review of current knowledge and consensus recommendations.
2008
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 Apr 1
Dicyanopyrazine-linked porphyrin Langmuir-Blodgett films.
2008 Apr 15
[Spectrum properties of Thulium bisphthalocyanine Langmuir-Blodgett films].
2008 Feb
Study of assembly of arachidic acid/LDHs hybrid films containing photoactive dyes.
2008 Feb 15
Chemically alternating Langmuir-Blodgett thin films as a model for molecular depth profiling by mass spectrometry.
2008 Jan
Unsaturated long-chain fatty acids induce the respiratory burst of human neutrophils and monocytes in whole blood.
2008 Jul 14
Characterization of Langmuir-Blodgett film using differential charging in X-ray photoelectron spectroscopy.
2008 Jul 24
Interrelated influence of superoxides and free fatty acids over mitochondrial uncoupling in skeletal muscle.
2008 Jul-Aug
Habitual fish consumption does not prevent a decrease in LCPUFA status in pregnant women (the Seychelles Child Development Nutrition Study).
2008 Jun
Hypocholesterolemic effects of fatty acid bile acid conjugates (FABACs) in mice.
2008 Mar 1
Orange-red luminescence from Cu doped CdS nanophosphor prepared using mixed Langmuir-Blodgett multilayers.
2008 Mar 21
Physico-chemical behaviour of the fish lipid from Lepidocephalus guntea (Hamilton) and variation of lipid profile with size.
2008 May 15
Depth resolution during C60+ profiling of multilayer molecular films.
2008 Oct 1
Distinct structural elements dictate the specificity of the type III pentaketide synthase from Neurospora crassa.
2008 Oct 20
Application of a pnCCD in X-ray diffraction: a three-dimensional X-ray detector.
2008 Sep
Characterization of domain growth kinetics in a mixed perfluorocarbon-hydrocarbon Langmuir-Blodgett monolayer.
2008 Sep 1
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Fri Dec 15 15:17:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:51 GMT 2023
Record UNII
PQB8MJD4RB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARACHIDIC ACID
INCI   MI  
INCI  
Official Name English
NSC-93983
Code English
ICOSANOIC ACID
Systematic Name English
EICOSANOIC ACID
Systematic Name English
ARACHIDIC ACID [INCI]
Common 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
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
NCI_THESAURUS C68439
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 75108-1
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
NCI_THESAURUS C68421
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
LOINC 16811-2
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
CFR 21 CFR 357.210
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
Code System Code Type Description
WIKIPEDIA
ARACHIDIC ACID
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
PUBCHEM
10467
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-031-3
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PRIMARY
SMS_ID
100000164879
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
CHEBI
32360
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
RXCUI
1716331
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C68321
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
MESH
C094477
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID1060134
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
CAS
506-30-9
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
NSC
93983
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
RXCUI
1716332
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
ALTERNATIVE
EVMPD
SUB179492
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PRIMARY
MERCK INDEX
m2023
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY Merck Index
FDA UNII
PQB8MJD4RB
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
CHEBI
28822
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
DAILYMED
PQB8MJD4RB
Created by admin on Fri Dec 15 15:17:51 GMT 2023 , Edited by admin on Fri Dec 15 15:17:51 GMT 2023
PRIMARY
Related Record Type Details
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LIPID -> FATTY ACID
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SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
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LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean. Low is a trace amount.
LIPID -> FATTY ACID
LIPID -> FATTY ACID
Trace value only.
LIPID -> FATTY ACID
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PARENT -> CONSTITUENT ALWAYS PRESENT