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> Linoleic acid [60-33-3]

Linoleic acid [60-33-3]

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Linoleic acid is a common polyunsaturated (PUFA) found in plant-based oils, nuts and seeds. Linoleic acid is a part of membrane phospholipids, and functions as a structural component to maintain a certain level of membrane fluidity of the transdermal water barrier of the epidermis. Linoleic acid induces red blood cells and hemoglobin damage via oxidative mechanism .

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Linoleic acid Chemical Structure

Linoleic acid Chemical Structure

CAS No. : 60-33-3

This product is a controlled substance and not for sale in your territory.

Based on 11 publication(s) in Google Scholar

Other Forms of Linoleic acid:

  • Linoleic acid-d4 Obtenir un devis
  • Linoleic acid-d11 Obtenir un devis
  • Linoleic acid-13C18 Obtenir un devis
  • Linoleic acid-13C1 Obtenir un devis
  • Linoleic acid-d5 Obtenir un devis
  • Linoleic acid-d2 Obtenir un devis
  • Linoleic acid (Standard) Obtenir un devis
Description

Linoleic acid is a common polyunsaturated (PUFA) found in plant-based oils, nuts and seeds. Linoleic acid is a part of membrane phospholipids, and functions as a structural component to maintain a certain level of membrane fluidity of the transdermal water barrier of the epidermis. Linoleic acid induces red blood cells and hemoglobin damage via oxidative mechanism [1][2].

Cellular Effect
Cell Line Type Value Description References
CHO EC50
1.8 μM
Compound: Linoleic acid
Agonist activity at human GPR40 expressed in CHO cells assessed as calcium flux by FLIPR assay
Agonist activity at human GPR40 expressed in CHO cells assessed as calcium flux by FLIPR assay
[PMID: 18993064]
CHO-K1 EC50
0.54 μM
Compound: Linoleic acid
Agonist activity at human GPR40 expressed in CHOK1 cells by fluorescence assay
Agonist activity at human GPR40 expressed in CHOK1 cells by fluorescence assay
[PMID: 18993064]
HEK293 EC50
4.8 μM
Compound: linoleic acid
Agonist activity at human FFA1 receptor expressed in HEK293 cells assessed as increase in intracellular Ca2+ flux by Fluo-4 dye based assay
Agonist activity at human FFA1 receptor expressed in HEK293 cells assessed as increase in intracellular Ca2+ flux by Fluo-4 dye based assay
[PMID: 30685095]
RBL-2H3 IC50
> 50 μM
Compound: 2
Antiallergic activity in rat RBL2H3 cells assessed as inhibition of DNP-HSA-mediated degranulation by measuring decrease in beta-hexosaminidase activity preincubated for 30 mins followed by DNP-HSA stimulation and measured after 30 mins by 4-nitrophenyl 2
Antiallergic activity in rat RBL2H3 cells assessed as inhibition of DNP-HSA-mediated degranulation by measuring decrease in beta-hexosaminidase activity preincubated for 30 mins followed by DNP-HSA stimulation and measured after 30 mins by 4-nitrophenyl 2
[PMID: 31618024]
In Vitro

Linoleic acid contains unsaturated double bonds that are highly vulnerable to free radical attack and oxidation. If ROS are produced in great quantities, the body can no longer efficiently remove them. In such instances, ROS may be released into the extracellular space, causing damage to surrounding cells and tissues. Linoleic acid is a decomposition product of a free fatty acid and has been linked to erythrocyte damage[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Linoleic acid Related Antibodies
Essai clinique
Masse moléculaire

280.45

Formule

C18H32O2
CAS No.

60-33-3
Appearance

Liquid (Density: 0.902 g/cm3)

Color

Colorless to light yellow

SMILES

CCCCC/C=C\C/C=C\CCCCCCCC(O)=O
Structure Classification
  • Ketones, Aldehydes, Acids
Initial Source
  • Endogenous metabolite
  • Disease markers
  • Endocrine diseases
  • Microorganisms
Livraison

Room temperature in continental US; may vary elsewhere.
Stockage

-20°C, protect from light, stored under nitrogen

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

Solvant et solubilité
In Vitro: 

DMSO : 100 mg/mL (356.57 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

0.1 M NaOH : 8.33 mg/mL (29.70 mM; ultrasonic and warming and adjust pH to 11 with NaOH and heat to 60°C)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.5657 mL 17.8285 mL 35.6570 mL
5 mM 0.7131 mL 3.5657 mL 7.1314 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

  • Calculateur de molarité

  • Calculateur de dilution

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass
=
Concentration
×
Volume
×
Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

×
Volume (start)

V1

=
Concentration (final)

C2

×
Volume (final)

V2

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.17 mg/mL (7.74 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.17 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (21.7 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.17 mg/mL (7.74 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.17 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (21.7 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  50% PEG300    50% Saline

    Solubility: 40 mg/mL (142.63 mM); Suspended solution; Need ultrasonic and warming and heat to 40°C

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO +
% 
+
%
Tween-80 +
%
Saline
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Pureté et documentation

Purity: 99.92%

SDS (393 KB)

COA (237 KB) HNMR (236 KB) RP-HPLC (190 KB) MS (67 KB)

Instruction de manipulation (2659 KB)
Références

  • [1]. Jay Whelan. Linoleic Acid. Adv Nutr. 2013 May; 4(3): 311–312.  [Content Brief]

    [2]. Yuan T, et al. Linoleic acid induces red blood cells and hemoglobin damage via oxidative mechanism. Int J Clin Exp Pathol. 2015 May 1;8(5):5044-52.  [Content Brief]

  • [1]. Jay Whelan. Linoleic Acid. Adv Nutr. 2013 May; 4(3): 311–312.

    [2]. Yuan T, et al. Linoleic acid induces red blood cells and hemoglobin damage via oxidative mechanism. Int J Clin Exp Pathol. 2015 May 1;8(5):5044-52.

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
0.1 M NaOH / DMSO 1 mM 3.5657 mL 17.8285 mL 35.6570 mL 89.1424 mL
5 mM 0.7131 mL 3.5657 mL 7.1314 mL 17.8285 mL
10 mM 0.3566 mL 1.7828 mL 3.5657 mL 8.9142 mL
15 mM 0.2377 mL 1.1886 mL 2.3771 mL 5.9428 mL
20 mM 0.1783 mL 0.8914 mL 1.7828 mL 4.4571 mL
25 mM 0.1426 mL 0.7131 mL 1.4263 mL 3.5657 mL
DMSO 30 mM 0.1189 mL 0.5943 mL 1.1886 mL 2.9714 mL
40 mM 0.0891 mL 0.4457 mL 0.8914 mL 2.2286 mL
50 mM 0.0713 mL 0.3566 mL 0.7131 mL 1.7828 mL
60 mM 0.0594 mL 0.2971 mL 0.5943 mL 1.4857 mL
80 mM 0.0446 mL 0.2229 mL 0.4457 mL 1.1143 mL
100 mM 0.0357 mL 0.1783 mL 0.3566 mL 0.8914 mL
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Linoleic acid Related Classifications

  • Metabolic Disease Cardiovascular Disease Cancer
  • Cancer Metabolism and Metastasis
  • Metabolic Enzyme/Protease
  • Endogenous Metabolite
Help & FAQs

Keywords:

Linoleic acid60-33-3Endogenous Metabolitepolyunsaturatedarachidonic acidessentialnutrientomega-6fattyacidplantoilshumanendogenousmetaboliteInhibitorinhibitorinhibit

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