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
[Effect of various substrate nutrient on the spore germination and infective germ tube inducing of Pandora delphacis].
2001 Apr
Structural elucidation of twelve novel esters composed of five fatty acids and three new branched alcohols together with four monoterpenoids from Sancassania shanghaiensis (Acari: Acaridae).
2001 Apr
Stable ordering in Langmuir-Blodgett films.
2001 Aug 17
Biosynthesis and structural characterization of medium-chain-length poly(3-hydroxyalkanoates) produced by Pseudomonas aeruginosa from fatty acids.
2001 Aug 20
Surface enhanced resonance Raman scattering imaging of Langmuir-Blodgett monolayers of bis (benzimidazo) thioperylene.
2001 May
Evaluation of phagocytosis and arachidonate metabolism by alveolar macrophages and recruited neutrophils from F344xBN rats of different ages.
2001 Oct
Temperature-related non-homogeneous fatty acid desaturation in sunflower (Helianthus annuus L.) seeds.
2003 Mar
Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids.
2003 May
Study of molecular interaction in the mixed film of arachidic acid and metal beta-diketonate complexes by the "surface ions" method.
2003 May 15
Characterizing the effects of saturated fatty acids on insulin signaling and ceramide and diacylglycerol accumulation in 3T3-L1 adipocytes and C2C12 myotubes.
2003 Nov 15
Behavior of Clostridium perfringens at low temperatures.
2004 Dec 1
J-aggregation and its characterization in Langmuir-Blodgett films of merocyanine dyes.
2004 Dec 13
Particle-rod hybrids: growth of arachidic acid molecular rods from capped cadmium selenide nanoparticles.
2004 Dec 22
Use of nutritional supplements to increase the efficacy of fluoxetine in the treatment of anorexia nervosa.
2004 Jan
Inhibition of formyl-methionyl-leucyl-phenylalanine-stimulated respiratory burst in human neutrophils by adrenaline: inhibition of Phospholipase A2 activity but not p47phox phosphorylation and translocation.
2004 Jan 1
Formation of a DNA layer on Langmuir-Blodgett films and its enzymatic digestion.
2004 Jul 6
Risk stratification by the "EPA+DHA level" and the "EPA/AA ratio" focus on anti-inflammatory and antiarrhythmogenic effects of long-chain omega-3 fatty acids.
2004 Nov
Acyl chain-based molecular selectivity for HL60 cellular phosphatidylinositol and of phosphatidylcholine by phosphatidylinositol transfer protein alpha.
2004 Nov 8
Morphological investigation of hybrid Langmuir-Blodgett films of arachidic acid with a hydrotalcite/dendrimer nanocomposite.
2004 Sep 28
Calcium signals activated by arachidonic acid in embryonic chick ciliary ganglion neurons.
2005
Infrared spectroscopy analysis of the structure of multilayer Langmuir-Blodgett films: effect of deposition velocity and pH.
2005 Jan 18
Biochemical and morphological changes in endothelial cells in response to hypoxic interstitial edema.
2006 Jan 13
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 Mar 10
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
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
Docosahexaenoic acid stabilizes soluble amyloid-beta protofibrils and sustains amyloid-beta-induced neurotoxicity in vitro.
2007 Feb
Ordering by collapse: formation of bilayer and trilayer crystals by folding Langmuir monolayers.
2007 Feb 13
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
[Determination of underivatized long-chain fatty acids in edible oils by fast gas chromatography].
2007 Mar
[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
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
Study of assembly of arachidic acid/LDHs hybrid films containing photoactive dyes.
2008 Feb 15
Unsaturated long-chain fatty acids induce the respiratory burst of human neutrophils and monocytes in whole blood.
2008 Jul 14
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
Physico-chemical behaviour of the fish lipid from Lepidocephalus guntea (Hamilton) and variation of lipid profile with size.
2008 May 15
Distinct structural elements dictate the specificity of the type III pentaketide synthase from Neurospora crassa.
2008 Oct 20
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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TUNISIAN SOURCE
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LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
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. Low is a trace amount.
LIPID -> FATTY ACID
LIPID -> FATTY ACID
Trace value only.
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)
PARENT -> CONSTITUENT ALWAYS PRESENT