Phospholipids

Phospholipids
Compound Structure:
Synonyms: LECITHIN; 8002-43-5; Soybean phospholipid ;17708-90-6 ;1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine
Compound ID: NMPC-1399
PubChem ID:

5287971

Molecular Formula: C42H80NO8P
Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC
InChIKey: JLPULHDHAOZNQI-ZTIMHPMXSA-N
About the compound:

Lecithin is a general term for a group of yellow-brownish fatty substances found in animal and plant tissues, characterized by their amphiphilic nature, meaning they attract both water and fatty substances. This dual attraction makes lecithin an effective smoothing agent for food textures, an emulsifier, and a homogenizer in liquid mixtures, as well as useful in repelling sticking materials. Composed mainly of glycerophospholipids including phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid, lecithin was first isolated in 1845 by French chemist ThéodoreGobley, who later named the phosphatidylcholine component "lécithine." Lecithin is both naturally occurring and man-made, presenting as a colorless-to-white solid in its pure form, though the commercial product is usually a liquid. It has a distinct sweet, tarry odor and can be identified by smell and taste at concentrations lower than those associated with harmful effects. While it evaporates more slowly than water, it can form a solution with water and is combustible. Widely used in the production of phenolic resins, nylon, synthetic fibers, slimicides, disinfectants, antiseptics, mouthwash, and sore throat lozenges, lecithin is versatile in various industrial applications. It can be extracted using solvents or mechanically from sources like egg yolk, marine foods, soybeans, milk, rapeseed, cottonseed, and sunflower oil. As a food additive, lecithin is valued for its non-toxic nature and its ability to act as a natural emulsifier or lubricant in food preparation. It plays key roles in confectionery, emulsions and fat spreads, doughs, baking, and as a component of cooking sprays. Recognized as "generally recognized as safe" by the United States Food and Drug Administration and designated as food additive E322 in the EU, lecithin is considered safe for human consumption. As a dietary supplement, lecithin is a source of choline, an essential nutrient. While there is no clinical evidence supporting its role in improving milk flow in breastfeeding mothers, higher maternal choline intake is potentially associated with better child neurocognition and neurodevelopment. Soy lecithin is generally safe for most people with soy allergies, and sunflower-derived lecithin serves as an alternative dietary supplement. In chemical terms, lecithin can be represented by specific phosphatidylcholines, such as 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine. It is a complex mixture of phospholipids, glycolipids, triglycerides, and other components, highlighting its diverse and multifaceted applications in various industries and as a dietary supplement.

GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 2114 of 2117 companies (only ~ 0.1% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

758.1 g/mol

XLogP3-AA

12.9

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

8

Rotatable Bond Count

40

Exact Mass

757.56215551 g/mol

Monoisotopic Mass

757.56215551 g/mol

Topological Polar Surface Area

111Ų

Heavy Atom Count

52

Formal Charge

0

Complexity

941

Isotope Atom Count

0

Defined Atom Stereocenter Count

1

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

2

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Waxy solid or thick liquid (dependent on acid value); White when fresh, turns yellow to brown on exposure to air; [Merck Index] Yellow odorless solid; [MSDSonline]

Melting Point

236-237 °C

Density

1.0305 at 24 °C/4 °C

Solubility 

Soluble in chloroform, ether, petroleum ether, mineral oils and fatty acids. Insoluble in acetone; practically insoluble in cold vegetable and animal oils.

Source: PubChem                        

Source Species: Lonchocarpus cyanescens
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