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(2S)-2-amino-3-[[(2R)-2-butanoyloxy-3-propanoyloxypropoxy]-hydroxyphosphoryl]oxypropanoic acid

HCID 6323481
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1446756-47-3
Standard SMILES
CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N)C(=O)O
InChIKey
UNJJBGNPUUVVFQ-ZJUUUORDSA-N
Molecular formula
C13H24NO10P
Average molar mass
385.3 g/mol
Monoisotopic mass
385.11378296

Overview

Phosphatidyl serine (PS) is a phospholipid nutrient found in fish, green leafy vegetables, soybeans and rice, and is essential for the normal functioning of neuronal cell membranes and activates Protein kinase C (PKC) which has been shown to be involved in memory function. In apoptosis, phosphatidyl serine is transferred to the outer leaflet of the plasma membrane. This is part of the process by which the cell is targeted for phagocytosis. PS has been shown to slow cognitive decline in animal models. PS has been investigated in a small number of double-blind placebo trials and has been shown to increase memory performance in the elderly. Because of the potentail cognitive benefits of phosphatidylserine, the substance is sold as a dietary supplement to people who believe they can benefit from an increased intake. The dietary supplement was originally processed from bovine sources however Prion disease scares in the 1990s outlawed this process, and a soy-based alternative was adopted.

Names & identifiers

Preferred name
(2S)-2-amino-3-[[(2R)-2-butanoyloxy-3-propanoyloxypropoxy]-hydroxyphosphoryl]oxypropanoic acid
IUPAC
(2S)-2-amino-3-[[(2R)-2-butanoyloxy-3-propanoyloxypropoxy]-hydroxyphosphoryl]oxypropanoic acid
English name
Lecithin
Molecular formula
C42H80NO8P
Molecular weight
758.06

Names & synonyms

SCHEMBL22762GTPL3638SCHEMBL27566251DB00144NS00070558Q2354337PHOSPHATIDYLCHOLINEL-α-PhosphatidylcholineLECITHIN LIQUIDLECITHIN POWDERLemonbottleSoybean phospholipids
Show more names
Modified soybean phospholipidl-α-phosphatidylcholine solutionL-α-LecithinLECITHIN SOYBEAN

Database identifiers

CAS
1446756-47-3、8002-43-5
PubChem CID
6323481

Properties

Computed structural properties

XLogP
-3.5
Topological polar surface area
172 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
11
Rotatable bonds
15
Heavy atoms
25
Formal charge
0
Complexity
497

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP-3.5
Solubility3.70e+00 g/L
Physical DescriptionSolid

Physicochemical properties

Melting point
145 °C · >145°C (dec.)
Density
424 · d424 1.0305
refractive index
1.4649 · 1.4649-1.4710
Flash point
Not applicable
storage temp.
-20 °C · -20°C
solubility
0.1 g/mL, · chloroform: 0.1 g/mL, slightly hazy, slightly yellow to deep orange
form
clear liquid to cloudy liquid
color
Orange to Brown
Odor
100 % · at 100.00%. bland fatty

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
1-8-10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
OG7565000
hs_code
29239000
Toxicity
LD50 oral in rat: > 8mL/kg
Signal word
Danger
Symbol(GHS)
GHS06,GHS08
Storage Class
3 - Flammable liquids
Hazard statements
H302-H315-H319-H331-H336-H351-H361d-H372
Hazard Classifications
Eye Irrit. 2Flam. Liq. 2
Precautionary statements
P202-P301+P312-P302+P352-P304+P340+P311-P305+P351+P338-P308+P313
Hazardous Substances Data
8002-43-5(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Phosphatidylserine is indicated in the treatment of cognitive impairment, including Alzheimer's disease, age-associated memory impairment and some non-Alzheimer's dementias. Further research is required before phosphatidylserine can be indicated for immune enhancement or for reduction of exercise stress. Phosphatidylserine was first isolated from brain lipids called cephalins. The major cephalins are phosphatidylserine and phophatidylethanolamine. Phosphatidylserine is involved in signal transduction activity as well as being a basic structural component of biologic membranes.

Mechanism of Action · 1 item

Cholinergic hypofunction is thought to account in part for the cognitive deficits found in Alzheimer's disease. The most commonly used drugs for the treatment of Alzheimer's disease are reversible acetylcholinesterase inhibitors. The rationale of these drugs is to increase acetylcholine levels in the brains of Alzheimer's patients, and they may be somewhat effective in some cases. Phosphatidylserine restores acetylcholine release in aging humans by maintaining an adequate supply of the molecule and is able to increase the availability of endogenous choline for de novo acetylcholine synthesis. The hippocampus of the brain is believed to be important for cognitive processes and is affected in those with Alzheimer's disease. The dendritic spines of pyramidal cells, the post-synaptic target of the excitatory input to the hippocampus, have been proposed as a substrate for information storage. Age-dependent dendritic spine loss in pyramidal neurons has been reported in the human brain, and the extent of synaptic loss appears to correlate with the degree of cognitive impairment. Phosphatidylserine treatment prevents the age-related reduction in dendritic spine density in rat hippocampus. Protein kinase C facilitation of acetylcholine release has been reported in rats. Phosphatidylserine was found to restore protein kinase C activity in aging rats. Stimulation of calcium uptake by brain synaptosomes and activation of protein kinase C are yet other speculative mechanisms of phosphatidylserine's putative cognition-enhancing action.

Metabolism/MetabolitesFollowing absorption, lysophosphatidylserine is metabolized in intestinal mucosa cells, and its metabolites, which include some phosphatidylserine, enter the lymphatics draining the small intestine.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
biological source
soybean
Water Solubility
NEGLIGIBLE
Merck
14 · 14,5429
BRN
5209585 · 5209585
Stability
Stable, but light, heat, moisture and air-sensitive. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions
ANTISTATICSKIN CONDITIONING - EMOLLIENTSKIN CONDITIONINGSURFACTANT - EMULSIFYING
Cosmetic Ingredient Review (CIR)
Lecithin (8002-43-5)
InChIKey
FWMYJLDHIVCJCT-VSZGHEPYSA-N
SMILES
[P](=O)([O-])(OC[C@H](OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCCCCCCCCCC)OCC[N+](C)(C)C
CAS DataBase Reference
8002 · 8002-43-5
SCOGS (Select Committee on GRAS Substances)
Lecithin
Substances Added to Food (formerly EAFUS)
LECITHIN
FDA 21 CFR
175.3 · 175.300; 176.170
EWG's Food Scores
1 · 1-3
FDA UNII
1 T6N4D9YV6 · 1T6N4D9YV6
Pesticides Freedom of Information Act (FOIA)
Lecithin
EPA Substance Registry System
Lecithins (8002-43-5)
Cosmetics Info
Lecithin
UNSPSC Code
51321705 · 51321705
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06,GHS08
Signal word
Danger
Hazard statements
302 · H302-H315-H319-H331-H336-H351-H361d-H372
Precautionary statements
202 · P202-P301+P312-P302+P352-P304+P340+P311-P305+P351+P338-P308+P313
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
WGK Germany
3 · 3
RTECS
7565000 · OG7565000
F
1 · 1-8-10
TSCA
TSCA listed
HS Code
29239000 · 29239000
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
2 Flam · Eye Irrit. 2Flam. Liq. 2
Hazardous Substances Data
8002 · 8002-43-5(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: > 8mL/kg
Absorption, Distribution and Excretion
Absorbed in the small intestine.
Cellular LocationsCytoplasm
Applications · 7 items

DescriptionFood-grade lecithin is obtained from soybeans and other plant sources. It is a complex mixture of acetone-insoluble phosphatides that consists chiefly of phosphatidyl choline, phosphatidyl etha nolamine, and phosphatidyl inositol, combined with various amounts of other substances such as triglycerides, fatty acids, and carbohydrates. Refined grades of lecithin may contain any of these components in varying proportions and combinations depending on the type of fractionation used. In its oil-free form, the prepon-derance of triglycerides and fatty acids is removed and the product contains 90% or more of phosphatides representing all or certain fractions of the total phosphatide complex. The consistency of both natural grades and refined grades of lecithin may vary from plastic to fluid, depending upon free fatty acid and oil content, and upon the presence or absence of other diluents. Its color varies from light yellow to brown, depending on the source, on crop variations, and on whether it is bleached or unbleached. It is odorless or has a characteristic, slight nutlike odor and a bland taste. Edible diluents, such as cocoa butter and vegetable oils, often replace soybean oil to improve functional and flavor characteris tics. Lecithin is only partially soluble in water, but it readily hydrates to form emulsions. The oil-free phosphatides are soluble in fatty acids, but are practically insoluble in fixed oils. When all phosphatide fractions are present, lecithin is partially soluble in alcohol and practically insoluble in acetone.

OccurrenceLecithin is found in foods such as eggs, beef liver, and peanuts. Commercial sources are available

Useslecithin (hydrogenated) is an emulsifier.

UsesEdible and digestible surfactant and emulsifier of natural origin. Used in margarine, chocolate and in the food industry in general. In pharmaceuticals and cosmetics. Many other industrial uses, e.g. treating leather and textiles.

Useslecithin is a natural emollient, emulsifier, anti-oxidant, and spreading agent, lecithin is a hydrophilic ingredient that attracts water and acts as a moisturizer. generally obtained for cosmetic products from eggs and soybeans, it is found in all living organisms.

Usesegg lecithin is emollient and particularly recommended for sensitive skin.

UsesLecithin is an emulsifier that is a mixture of phosphatides which are typically surface-active. it is now commercially obtained from soy- beans; previously it was obtained from egg yolk. it is used in marga- rine as an emulsifier and antispatter agent; in chocolate manufacture it controls flow properties by reducing viscosity and reducing the cocoa butter content from 3 to 5%; it is used as a wetting agent in cocoa powder, fillings, and beverage powders; an antisticking agent in griddling fat; and in baked goods to assist the shortening mix with other dough ingredients and to stabilize air cells. typical usage levels range from 0.1 to 1.0%.

Upstream & downstream products

Upstream raw materials

Soy bean phospholipidASPHALTUMSoybean oilCalcium phytateSoy bean Isoflavone Isoflavone 10-40%PASSION FLOWER OILPartialFattyAcidEsterofGlycerineVacuum drying machineEthanol solutionCholesterol

Downstream products

PhosphatidylethanolamineSoy bean phospholipidPHOSPHOLIPIDSEthyl linoleate

Additional notes

DefinitionChEBI: A glycerophosphocholine compound having O-acyl substituents at both the 1- and 2-positions of the glycerol. It is a major constituent of cell membranes.