9,12-Octadecadienoic acid

9,12-Octadecadienoic acid
Compound Structure:
Synonyms: 9,12-Octadecadienoic acid;2197-37-7;octadeca-9,12-dienoic acid;alpha-Linoleic acid;cis-9-cis-12-Octadecadienoic acid;9,12-octadecadienic acid;CBiol_001994;KBioGR_000094; Bio2_000574;8024-22-4;85594-37-2;9(E),12(Z)-Octadecadienoic acid
Compound ID: NMPC-517
PubChem ID:

3931

Molecular Formula: C18H32O2
Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)O
InChIKey: OYHQOLUKZRVURQ-UHFFFAOYSA-N
About the compound:

Linoleic acid, also known as 9,12-Octadecadienoic acid, is a polyunsaturated fatty acid (PUFA) that is essential for human health. It is predominantly found in various vegetable oils and plays a crucial role in the human diet[1]. This acid is chemically identified by its molecular formula, C18H32O2, and has a molecular weight of about 280.4455 g/mol. It is notable for its two cis double bonds at the 9th and 12th carbon positions, which are essential for several biological functions including maintaining the structural integrity of cell membranes and the production of signaling molecules[2]. In terms of its physical characteristics, linoleic acid has a melting point near 266 K and a much higher boiling point of around 765 K under certain conditions. Its critical temperature and pressure, along with changes in density and phase transitions, are well-studied, making this knowledge crucial for both scientific research and practical applications[1]. Linoleic acid also contributes to the synthesis of related chemical substances and is utilized in various industrial processes, including the food and cosmetics sectors, where its derivatives are incorporated into products from margarines to beauty creams[3,4].

References 

1. Cheméo. (n.d.). 9,12-Octadecadienoic acid (Z,Z) - CAS 60-33-3 - Chemical & Physical Properties by Cheméo. Retrieved from https://www.chemeo.com

2. ChemSpider. (n.d.). 9,12-Octadecadienoic acid. Retrieved from http://www.chemspider.com/Chemical-Structure.4444650.html

3. National Institute of Standards and Technology. (n.d.). 9,12-Octadecadienoic acid (Z,Z)-. Retrieved from https://webbook.nist.gov

4. Wikipedia. (2021, January 4). Octadecadienoic acid. Retrieved from https://en.wikipedia.org/wiki/Octadecadienoic_acid

GHS Hazard Statements

H226 (97.3%): Flammable liquid and vapor [Warning Flammable liquids]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

280.4 g/mol

XLogP3

6.8

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

14

Exact Mass

280.240230259 g/mol

Monoisotopic Mass

280.240230259 g/mol

Topological Polar Surface Area

37.3Ų

Heavy Atom Count

20

Formal Charge

0

Complexity

267

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

2

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem

Source Species: Dyschoriste perrottetii
Funtumia africana
Lagenaria siceraria
Persea americana
Piper guineense
Tetracarpidium conophorum
Vernonia amygdalina
Xylopia aethiopica
Zanthoxylum zanthoxyloides
Piliostigma thonningii.
Tragia benthamii
Azanza garckeana
Pyrenacantha staudtii
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