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Phosphatidyl choline (from Soybean)

Alias: LECITHIN; Soybean phospholipid; 17708-90-6; 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine; Azolectin; 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine; PALMITOYL-LINOLEOYL PHOSPHATIDYLCHOLINE; Soybean lecithin;
Cat No.:V19713 Purity: ≥98%
Phosphatidyl cholines (from egg yolk) are a class of phospholipids with choline as a headgroup.
Phosphatidyl choline (from Soybean)
Phosphatidyl choline (from Soybean) Chemical Structure CAS No.: 8002-43-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
1g
Other Sizes

Other Forms of Phosphatidyl choline (from Soybean):

  • Phosphatidyl choline (from egg yolk)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Description: Phosphatidyl cholines (from egg yolk) are a class of phospholipids with choline as a headgroup. As the major component of biological membranes, they can be easily obtained from a variety of readily available sources, such as egg yolk or soybeans, from which they are mechanically or chemically extracted using hexane. They are also a member of the lecithin group of yellow-brownish fatty substances occurring in animal and plant tissues. Dipalmitoyl phosphatidylcholine (aka: lecithin) is a major component of pulmonary surfactant and is often used in the L/S ratio to calculate fetal lung maturity. While phosphatidylcholines are found in all plant and animal cells, they are absent in the membranes of most bacteria, including Escherichia coli. Purified phosphatidylcholine is produced commercially.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
After cultivating in MRS broth with 0.2 to 1.0% soybean lecithin, cells extracted in a 0.3% bile challenge showed significantly higher survival rates (P<0.05) compared to the group without soybean lecithin. Cells treated with 0.6% soybean lecithin were able to grow in MRS broth with a greater bile salt concentration. In the presence of soybean lecithin, cell surface hydrophobicity and membrane integrity improved during bile challenge. alterations in fatty acid content were also seen in soybean Lecithin cultures, indicating alterations in cell membranes [1].
Toxicity/Toxicokinetics
Toxicity Summary
Identification and Uses: Lecithin is waxy when its acid value is approximately 20; it becomes a pourable, viscous liquid when its acid value is approximately 30. It is a natural, edible, digestible surfactant and emulsifier. It is widely used in margarine, chocolate, and the food industry. Additionally, it is used in the pharmaceutical and cosmetic industries. It has many other industrial uses, including the treatment of leather and textiles. It is also used as an experimental drug. Human Exposure and Toxicity: In clinical irritation studies, cosmetic formulations containing 0.3% or 3% 65% lecithin (65% lecithin solution), soaps containing 0.83% lecithin powder (test concentration 0.5%), and lecithin liposomes are generally non-irritating. The most serious reaction observed was a barely perceptible erythema. Hydrogenated lecithin is non-irritating, and hydrogenated lecithin (15% petrolatum solution) is not sensitizing. Furthermore, tanning oils containing 3% 65% lecithin, mascaras containing 0.1% 65% lecithin, and foundations containing 0.3% 65% lecithin were not sensitizing. To improve human work capacity, subjects were given 22 to 83 grams of lecithin daily for 2 to 4 months, and no adverse reactions were observed. However, lecithin contaminated with soy protein and used as a pharmaceutical excipient may cause reactions in patients with soy allergies. Foundations containing 0.3% 65% lecithin (65% lecithin solution) did not show photosensitivity in human subjects. Animal studies: In a single-stimulation patch test (rabbit), 65% lecithin solution showed very low skin irritation in rabbits, products containing 3% 65% lecithin showed almost zero or slight skin irritation in rabbits, and products containing 2.25% 65% lecithin showed no skin irritation in rabbits. In guinea pig immersion tests, 0.5% soap containing 0.83% lecithin powder showed almost no skin irritation in guinea pigs. 65% lecithin solutions and products containing 2.25% or 3.0% 65% lecithin showed very low or no irritation to unrinsed rabbit eyes. Soap containing 0.83% lecithin powder (test concentration 25%) was moderately irritating, while liposomes containing lecithin showed almost no irritation in the Draize test. Mice exposed to aerosol lecithin for 4 hours daily for two consecutive days developed focal endothelial cell swelling and interstitial edema in the lungs. One group of mice was fed 5–10 mg of lecithin mixed with sugar (to improve palatability), while another group was fed lecithin (5–10 mg) and cholesterol (4–5 mg). Mice were bred, and their offspring were administered the same procedure; administration continued until all mice were near death or died. Control group mice had free access to laboratory feed. The total number of mice fed lecithin, lecithin and cholesterol, and control diets were 166, 212, and 360, respectively. After sacrifice, brain autopsies were performed. Neuroblastomas were found in 18 of the 73 animals fed lecithin; neuroblastomas were found in 27 of the 88 animals fed lecithin and cholesterol; and no neuroblastomas were found in any of the 188 control animals.
Effects during pregnancy and lactation
◉ Overview of use during lactation
Lecithin is a mixture of choline, choline esters, fatty acids, glycerol, glycolipids, triglycerides, phosphoric acid, and phospholipids (such as phosphatidylcholine), all normal components of human milk. Lecithin supplementation has been recommended for the treatment of blocked mammary ducts and is added as an additive to human milk pumped to premature infants through plastic tubes to prevent fat loss. Currently, there are no scientifically valid clinical studies to confirm the safety and efficacy of high-dose lecithin supplements for breastfeeding women or infants. Most breastfeeding women have insufficient choline intake, and the choline content in the breast milk of mothers of premature infants may be reduced. One of the components of lecithin supplements—phosphatidylcholine—can increase the concentration of choline in breast milk, but does not increase the concentration of phosphatidylcholine; choline supplementation can increase the concentration of choline metabolites in breast milk, but does not increase the concentration of choline. A meta-analysis found that higher maternal choline intake may be associated with better neurocognitive and neurodevelopment in children. Lecithin is generally well-tolerated and is recognized as "Generally Recognized As Safe" (GRAS) by the U.S. Food and Drug Administration (FDA). Dietary supplements do not require extensive premarket approval from the FDA. Manufacturers are responsible for ensuring the safety of their products, but are not required to prove their safety and efficacy before marketing them. Dietary supplements may contain multiple ingredients, and the ingredients listed on the label often differ from the actual ingredients or amounts. Manufacturers may commission independent agencies to verify the quality of their products or their ingredients, but this does not guarantee the safety and efficacy of the product. Given the above issues, clinical trial results for one product may not be applicable to other products. For more detailed information on dietary supplements, please visit other pages on the LactMed website.
◉ Effects on breastfed infants
No published information found as of the revision date.
◉ Effects on lactation and breast milk
No published information found as of the revision date.
References

[1]. Biochemical reagents[M]//Methods of Enzymatic Analysis. Academic Press, 1965: 967-1037.

Additional Infomation
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycerol-3-phosphocholine is a phosphatidylcholine 34:2, wherein the 1- and 2-acyl groups are designated as hexadecanoyl (palmitoyl) and 9Z,12Z-octadecadienoyl (linoleoyl), respectively. It is a complex mixture of phosphatidylcholine 34:2 and 1-acyl-2-linoleoyl-sn-glycerol-3-phosphocholine betaine. It is a complex mixture of phospholipids, glycolipids, triglycerides, phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol.
It has been reported that 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycerol-3-phosphate choline has been found in Drosophila melanogaster, Lycoris radiata, and Vitis vinifera, with relevant data available.
Lecithin is a phospholipid whose polar choline is linked to diacylglycerol via a phosphate ester bond.
Therapeutic Uses
Surfactant
/EXPL THER/ Endosulfan, a common organochlorine pesticide in aquatic environments, has been found to reduce the heat tolerance of fish. Lipid-stimulating agents such as lecithin have been shown to improve the heat tolerance of fish. This study aimed to evaluate the role of a lipid-stimulating agent (lecithin) in improving the heat tolerance of black bass (Chanos chanos) under sublethal low-dose endosulfan stress. 225 fish were randomly assigned to 5 treatment groups, with 3 replicates per treatment group. Four isocaloric and isonitrogenous diets were prepared and supplemented with different concentrations of lecithin: a normal water group fed the control diet (En0/L0); an endosulfan-treated group fed the control diet (En/L0); and endosulfan-treated groups fed diets supplemented with 1% (En/L1%), 1.5% (En/L1.5%), and 2% (En/L2%) lecithin, respectively. The concentration of endosulfan in the treated water was maintained at 1/40 of the LC50 (0.52 ppb). After five weeks, the critical maximum temperature (CTmax), lethal maximum temperature (LTmax), critical minimum temperature (CTmin), and lethal minimum temperature (LTmin) were measured. Compared with the control group and the endosulfan-exposed group, the temperature tolerance (CTmax, LTmax, CTmin, and LTmin) of the diets supplemented with 1%, 1.5%, and 2% lecithin were significantly affected (P<0.01). Positive correlations were found between CTmax and LTmax (R²=0.934) and between CTmin and LTmin (R²=0.9313). At the end of the heat tolerance study, dietary lecithin significantly improved changes in endethionein-induced cellular stress kinases (catalase, superoxide dismutase, and glutathione S-transferase in the liver and gills, and the neurotransmitter enzyme acetylcholinesterase in the brain) (p<0.01). This paper reports the role of lecithin in enhancing the heat tolerance of fish exposed to organochlorine pesticides and protecting them from cellular stress. The suitability of liquid lecithin (i.e., a solution of lecithin in soybean oil with a phospholipid content of approximately 60% w/w) for gel formation after the addition of poloxamer 407 aqueous solution was investigated, and the formulated system was evaluated as a carrier for transdermal ibuprofen administration. Formulation studies were conducted on a lecithin/poloxamer 407/water ternary system under a constant lecithin/poloxamer 407 mass ratio of 2.0. The results showed that the minimum concentrations of lecithin and poloxamer 407 required to form a gel-like system were 15.75% (w/w) and 13.13% (w/w), respectively, while the maximum water content was 60.62% (w/w). Systems with water content ranging from 55% to 60.62% (w/w) were soft semi-solids suitable for topical applications and were selected for physicochemical and biopharmaceutical evaluation. Conductivity analysis and optical microscopy observations indicated that the studied system was a water-soluble dispersion of spherical oligomeric layered assemblages formed by phospholipid and triglyceride molecules in an aqueous copolymer solution. Rheological behavior evaluation results indicated that the studied gel was a thermosensitive shear-thinning system. Ibuprofen (5% w/w) was dispersed in a pre-prepared carrier. The drug delivery system was stable for 30 days at storage temperatures ranging from 5 ± 3 °C to 40 ± 2 °C. In vitro ibuprofen release conformed to the Higuchi model (rH>0.95) and was sustained for 12 hours. These results indicate that the optimized LLPBG formulation, with optimized drug release and sensory properties, holds promise as a carrier for sustained transdermal administration of poorly soluble drugs.
/EXPL THER/ Some dietary factors may inhibit lead poisoning. This study aimed to evaluate the effects of dietary compounds rich in unsaturated fatty acids (FA) on blood lead levels, lipid metabolism, and vascular reactivity in rats. The possible mechanisms by which unsaturated fatty acids affect blood lead levels were explored by detecting serum metallothionein and organ lead levels. Male Wistar rats, who drank water containing lead (100 ppm Pb) or lead acetate-free water, were orally supplemented daily with either virgin olive oil or flaxseed oil (0.2 mL/kg body weight) or the lecithin component "Super Lecithin" (50 g/kg body weight). In in vitro experiments, mesenteric arteries were stimulated with six different doses of norepinephrine (NE). Lecithin supplementation slightly reduced the arterial pressor response to NE. Lead supplementation in rats weakened the beneficial effects of unsaturated fatty acids on lipid metabolism and vascular response to adrenergic stimulation. On the other hand, super lecithin and flaxseed oil, with a low ω-6/ω-3 ratio (approximately 1), reduced blood lead levels. This effect was observed in both lead-poisoned rats (p < 0.0001) and non-lead-poisoned rats (p < 0.05). For more complete data on the therapeutic uses of lecithin (9 types), please visit the HSDB record page.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C42H80NO8P
Molecular Weight
758.0603
Exact Mass
757.562
CAS #
8002-43-5
Related CAS #
8057-53-2 (from egg yolk);8002-43-5 (from Soybean);
PubChem CID
5287971
Appearance
Color is nearly white when freshly made, but rapidly becomes yellow to brown in air
Light-brown to brown, viscous semiliquid
Waxy mass when the acid value is about 20; pourable, thick fluid when the acid value is around 30
Density
1.0305 g/cm3 (20ºC)
Melting Point
236.1ºC
Flash Point
57 °C
LogP
10.9
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
40
Heavy Atom Count
52
Complexity
941
Defined Atom Stereocenter Count
1
SMILES
P(=O)([O-])(OC([H])([H])[C@@]([H])(C([H])([H])OC(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O)OC(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])=C([H])C([H])([H])C([H])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O)OC([H])([H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
InChi Key
JLPULHDHAOZNQI-ZTIMHPMXSA-N
InChi Code
InChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1
Chemical Name
[(2R)-3-hexadecanoyloxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
Synonyms
LECITHIN; Soybean phospholipid; 17708-90-6; 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine; Azolectin; 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine; PALMITOYL-LINOLEOYL PHOSPHATIDYLCHOLINE; Soybean lecithin;
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~10 mg/mL (~13.19 mM)
DMSO : ~5 mg/mL (~6.60 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 0.5 mg/mL (0.66 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 0.5 mg/mL (0.66 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 0.5 mg/mL (0.66 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.3192 mL 6.5958 mL 13.1916 mL
5 mM 0.2638 mL 1.3192 mL 2.6383 mL
10 mM 0.1319 mL 0.6596 mL 1.3192 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
A Randomized, Double-Blind, Parallel-Group Clinical Trial to Assess the Efficacy of Essentiale on Hepatic Steatosis Added to Standard of Care Versus Placebo Added to Standard of Care, in Non-Alcoholic Fatty Liver
EudraCT: 2021-006069-39
Phase: Phase 4
Status: Completed
Date: 2022-06-26
Randomized, double-blind, double-dummy, placebo-controlled, Phase III clinical trial on the efficacy and safety of a 48-weeks treatment with gastro-resistant phosphatidylcholine (LT-02) versus placebo versus mesalamine for maintenance of remission in patients with ulcerative colitis
EudraCT: 2013-001205-84
Phase: Phase 3
Status: Completed
Date: 2015-01-13
Randomized, double-blind, double-dummy, placebo-controlled, Phase III clinical trial on the efficacy and safety of a 12-weeks add-on treatment with LT-02 (gastro-resistant phosphatidylcholine granules) vs. placebo in patients with ulcerative colitis refractory to standard treatment with mesalamine
EudraCT: 2012-003702-27
Phase: Phase 3
Status: Prematurely Ended, Completed
Date: 2014-05-08
A Prospective, Randomized, Double-blind, Placebo Controlled, Dose Ranging, Multi-Center Study of the Safety and Efficacy of Three Days Continuous Intravenous Infusion of GR270773 in the Treatment of Suspected or Confirmed Gram-negative Severe Sepsis in Adults.
EudraCT: 2004-000406-51
Phase: Phase 2
Status: Completed
Date: 2004-09-16
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