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L1376

α-Linoleic acid

≥98%

Synonym(s):

Linoleic acid

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About This Item

Linear Formula:
CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
CAS Number:
60-33-3
Molecular Weight:
280.45
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
24896279
EC Number:
200-470-9
Beilstein/REAXYS Number:
1727101
MDL number:
MFCD00064241
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biological source

plant oil (safflower)

Quality Level

200

assay

≥98%

form

liquid

color

colorless

refractive index

n20/D 1.466

bp

229-230 °C/16 mmHg

mp

−5 °C

application(s)

life science and biopharma

functional group

carboxylic acid

lipid type

omega FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

OC(CCCCCCC/C=C\C/C=C\CCCCC)=O

InChI

1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

InChI key

OYHQOLUKZRVURQ-HZJYTTRNSA-N

Gene Information

human ... SOAT1(6646), SOAT2(8435)

General description

Linoleic acid is considered an important dietary omega-6 fatty acid. It contributes to the structural components of cell membranes.

Application

Linoleic acid has been used as a substrate to measure lipoxygenase activity. It has also been used to prepare linoleic acid hydroperoxide samples and study the prooxidant activity of citrate-stabilized CeO2.[1]

Biochem/physiol Actions

Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes citation.
Linoleic acid is an n-6 polyunsaturated essential fatty acid (PUFA) used as a precursor of arachidonic acid (AA) and various prostaglandins. Linoleic acid may be used to improve the delivery and efficacy of anticancer drugs and in cancer protection. Linoleic acid has a significant influence on the membrane function. This fatty acid serves as a precursor for the bioactive metabolites called eicosanoids, which regulate renal and pulmonary function, vascular tone, and inflammatory responses. Linoleic acid deficiency has been observed in infants with chronic fat malabsorption conditions. Insufficient levels of this fatty acid result in poor growth and development in infants, scaly dermatitis, and an impaired immune response. Linoleic acid maintains the skin’s moisture content, hence it is utilized in topical applications.

Other Notes

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1 of 1

This Item
62240L1012W338020
α-Linoleic acid ≥98%

Sigma-Aldrich

L1376

α-Linoleic acid

Linoleic acid technical, 58-74% (GC)

Sigma-Aldrich

62240

Linoleic acid

Linoleic acid liquid, BioReagent, suitable for cell culture

Sigma-Aldrich

L1012

Linoleic acid

Linoleic acid ≥95%, FG

Sigma-Aldrich

W338020

Linoleic acid

assay

≥98%

assay

-

assay

≥98%

assay

≥95%

functional group

carboxylic acid

functional group

carboxylic acid

functional group

-

functional group

-

biological source

plant oil (safflower)

biological source

-

biological source

plant (Safflower oil)

biological source

synthetic

shipped in

ambient

shipped in

-

shipped in

-

shipped in

-

form

liquid

form

liquid

form

liquid

form

-

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

2-8°C

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000561593
0000563441
0000561271
0000546539
0000546540

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Fatty acids: Omega-6 polyunsaturated
Benjamin Caballero
Encyclopedia of Human Nutrition, 232-238 (2013)
Inactivation of soybean lipoxygenase in soymilk by pulsed electric fields
Li YQ, et al.
Food Chemistry, 109(2) (2008)
Introduction: the role of fats in human diet
Sanders, Thomas AB
Functional Dietary Lipids (2016)
View All Related Papers

Global Trade Item Number

SKUGTIN
L1376-5G04061835545957
L1376-1G04061835518173
L1376-10MG04061835545926
L1376-500MG04061835545940
L1376-10G04061835545919
L1376-25G04061835545933

Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. I noticed it comes as a liquid. What does it coke dissolved in?

    1 answer

    1. This product is not diluted with any solvent. The physical form is a liquid. It is considered a 'neat' product with a minimum purity of 99%. The density is 0.902 g/mL at room temperature. The product is sold by weight, the 5 gram package would be approx. 5.5 mL.

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