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Arachidonic acid

Alias: arachidonic acid; 506-32-1; (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid; (all-Z)-5,8,11,14-Eicosatetraenoic acid; cis-5,8,11,14-Eicosatetraenoic acid; 5,8,11,14-Eicosatetraenoic acid, (all-Z)-; all-cis-5,8,11,14-eicosatetraenoic acid; Arachidonsaeure;
Cat No.:V30372 Purity: ≥98%
Arachidonic acid is an essential fatty acid and is a major component of biological membranes.
Arachidonic acid
Arachidonic acid Chemical Structure CAS No.: 506-32-1
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
100mg
Other Sizes

Other Forms of Arachidonic acid:

  • Arachidonic acid-d8 (Immunocytophyt-d8)
  • Arachidonic acid-d5 (Immunocytophyt-d5)
  • Arachidonic acid-d11 (Immunocytophyt-d11)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Arachidonic acid is an essential fatty acid and is a major component of biological membranes.
Arachidonic acid is a long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia galeata metabolite and a mouse metabolite. It is an icosa-5,8,11,14-tetraenoic acid, an omega-6 fatty acid and a long-chain fatty acid. It is a conjugate acid of an arachidonate. It derives from a hydride of a (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene.
Arachidonic Acid is an unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.(ChemID Plus) Arachidonic Acid is an unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.
Biological Activity I Assay Protocols (From Reference)
Targets
Endogenous Metabolite; Cyclooxygenase (COX); Lipoxygenase (LOX)[1]
ln Vivo
In a rat adjuvant-induced arthritis (AIA) model, dietary supplementation with arachidonic acid (1% w/w in feed for 7 weeks) significantly increased arachidonic acid content in paw tissues by 2.3-fold compared to control. However, it did not alter arthritis severity (measured by paw swelling and clinical scores) or paw prostaglandin E₂ (PGE₂) content, indicating no pro-inflammatory exacerbation.

Serum analysis confirmed elevated arachidonic acid levels in supplemented rats but showed no correlation with disease progression or systemic PGE₂ changes.[1]
In animal modeling, arachidonic acid can be utilized to create an obese foot model.
Animal Protocol
AIA Model: Female Lewis rats received 1% (w/w) arachidonic acid in standard chow for 7 weeks (starting 1 week pre-adjuvant injection). Arthritis was induced at day 0 by intradermal tail injection of heat-killed Mycobacterium tuberculosis in mineral oil. Paw swelling was measured weekly; tissues/serum were collected at endpoint for lipidomics and PGE₂ analysis.[1]
ADME/Pharmacokinetics
Metabolism / Metabolites
Arachidonic acid has known human metabolites that include 17-HETE, 18-HETE, 8,9-EET, 20-HETE, 9-HETE, 8-HETE, 5-HETE, 11-HETE, 11,12-EET, 5,6-EET, 13-HETE, 7-HETE, 10-HETE, 12-HETE, 14,15-EET, 15-HETE, 16-HETE, and 19-HETE.
Toxicity/Toxicokinetics
Toxicity Summary
Cosmetic Ingredient Review Conclusion The safety of this ingredient has not been documented and substantiated for cosmetic product use. The CIR Expert Panel cannot conclude whether Arachidonic Acid is safe for use in cosmetic products until such time that the appropriate safety data have been obtained and evaluated.
Ingredients for which the data are insufficient and their use in cosmetics is not supported
References

[1]. Dietary supplementation with arachidonic acid increases arachidonic acid content in paw, but does not affect arthritis severity or prostaglandin E2 content in rat adjuvant-induced arthritis model. Lipids Health Dis. 2015 Jan 16;14:3.

Additional Infomation
Arachidonic acid is an ω-6 polyunsaturated fatty acid serving as a precursor for inflammatory eicosanoids like PGE₂. This study demonstrates that increased tissue arachidonic acid availability does not necessarily translate to amplified inflammation in arthritis.

The dissociation between tissue arachidonic acid content and PGE₂ levels suggests complex regulatory mechanisms in eicosanoid biosynthesis during chronic inflammation.[1]
Arachidonic acid is a long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia galeata metabolite and a mouse metabolite. It is an icosa-5,8,11,14-tetraenoic acid, an omega-6 fatty acid and a long-chain fatty acid. It is a conjugate acid of an arachidonate. It derives from a hydride of a (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene.
Arachidonic acid has been reported in Agaricus blazei, Mortierella hygrophila, and other organisms with data available.
Arachidonic Acid is an unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.(ChemID Plus)
An unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H32O2
Molecular Weight
304.4669
Exact Mass
304.24
Elemental Analysis
C, 78.90; H, 10.59; O, 10.51
CAS #
506-32-1
Related CAS #
Arachidonic acid-d8;69254-37-1;Arachidonic acid-d5;123167-26-0;Arachidonic acid-d11;2692624-11-4
PubChem CID
444899
Appearance
Colorless to light yellow liquid
Density
0.9±0.1 g/cm3
Boiling Point
407.5±0.0 °C at 760 mmHg
Melting Point
−49 °C(lit.)
Flash Point
336.3±18.0 °C
Vapour Pressure
0.0±2.0 mmHg at 25°C
Index of Refraction
1.501
LogP
6.91
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
14
Heavy Atom Count
22
Complexity
362
Defined Atom Stereocenter Count
0
SMILES
O([H])C(C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
InChi Key
YZXBAPSDXZZRGB-DOFZRALJSA-N
InChi Code
InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
Chemical Name
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Synonyms
arachidonic acid; 506-32-1; (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid; (all-Z)-5,8,11,14-Eicosatetraenoic acid; cis-5,8,11,14-Eicosatetraenoic acid; 5,8,11,14-Eicosatetraenoic acid, (all-Z)-; all-cis-5,8,11,14-eicosatetraenoic acid; Arachidonsaeure;
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~328.44 mM)
Ethanol : ~100 mg/mL (~328.44 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (8.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.83 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.


Solubility in Formulation 4: 10 mg/mL (32.84 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2844 mL 16.4220 mL 32.8440 mL
5 mM 0.6569 mL 3.2844 mL 6.5688 mL
10 mM 0.3284 mL 1.6422 mL 3.2844 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
Omega Tots Long Term Follow-up
CTID: NCT05191823
Phase: N/A
Status: Enrolling by invitation
Date: 2025-05-11
The Role of Fatty Acids in Vaccine Efficacy
CTID: NCT05987384
Phase: N/A
Status: Completed
Date: 2023-08-14
Omega Tots: A Randomized, Controlled Trial of Long-chain Polyunsaturated Fatty Acid Supplementation of Toddler Diets and Developmental Outcomes
CTID: NCT01576783
Phase: Phase 4
Status: Completed
Date: 2021-06-29
Arachidonic Acid Treatment Against Schistosomiasis Infection in Children
CTID: NCT02144389
Phase: N/A
Status: Completed
Date: 2014-05-22
Assessment of Arachidonic Acid Supplementation in Infant Formula on the Immune Response of Infants
CTID: NCT02092857
Phase: Phase 1
Status: Completed
Date: 2014-04-25
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