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Cas Database

4235-95-4

4235-95-4

Identification

  • Product Name:3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium,4-hydroxy-N,N,N-trimethyl-10-oxo-7-[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]-, innersalt, 4-oxide, (7R,18Z)-

  • CAS Number: 4235-95-4

  • EINECS:224-193-8

  • Molecular Weight:786.127

  • Molecular Formula: C44H84NO8P

  • HS Code:29232000

  • Mol File:4235-95-4.mol

Synonyms:3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium,4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxo-9-octadecenyl)oxy]-, hydroxide,inner salt, 4-oxide, [R-(Z,Z)]-;3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium,4-hydroxy-N,N,N-trimethyl-10-oxo-7-[[(9Z)-1-oxo-9-octadecenyl]oxy]-, innersalt, 4-oxide, (7R,18Z)- (9CI);Choline phosphate, 3-ester with L-1,2-diolein(6CI);Choline, hydroxide, dihydrogen phosphate, inner salt, ester withL-1,2-diolein (8CI);Olein, 1,2-di-, L-, dihydrogen phosphate, monoester withcholine hydroxide (8CI);1,2-Dioleoyl-L-a-lecithin;1,2-Dioleoyl-sn-glycero-3-phosphatidylcholine;1,2-Dioleoyl-sn-glycero-3-phosphocholine;1,2-Dioleoyl-sn-glycero-3-phosphorylcholine;1,2-Dioleoyl-sn-glycerol-3-phosphorylcholine;1,2-Dioleoyl-sn-phosphatidylcholine;1,2-Dioleyl-sn-glycero-3-phosphorylcholine;3,5,9-Trioxa-4-phosphaheptacos-18-en-1-aminium,4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxo-9-octadecenyl)oxy]-, inner salt,4-oxide, [R-(Z,Z)]-;DOPC;Dioleoyl L-a-lecithin;Dioleoyl-3-sn-phosphatidylcholine;Dioleoyl-L-a-glycerophosphocholine;Dioleoyl-L-a-glycerophosphorylcholine;Dioleoyl-L-a-phosphatidylcholine;Dioleoylphosphatidylcholine;L-Dioleoyl lecithin;L-a-Di(cis-9-octadecanoyl) lecithin;L-a-Dioleoyl phosphatidylcholine;L-a-Dioleoyllecithin;L-a-Dioleylphosphatidylcholine;PDD111;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:TRC
  • Product Description:1,2-Dioleoyl-sn-glycero-3-phosphocholine
  • Packaging:500mg
  • Price:$ 685
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,2-Dioleoyl-sn-glycero-3-phosphocholine >97.0%(HPLC)(T)
  • Packaging:250mg
  • Price:$ 87
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,2-Dioleoyl-sn-glycero-3-phosphocholine lyophilized powder
  • Packaging:1g
  • Price:$ 463
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,2-Dioleoyl-sn-glycero-3-phosphocholine lyophilized powder
  • Packaging:25mg
  • Price:$ 56.6
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,2-Dioleoyl-sn-glycero-3-phosphocholine lyophilized powder
  • Packaging:100mg
  • Price:$ 102
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  • Manufacture/Brand:Chem-Impex
  • Product Description:1,2-Dioleoyl-sn-glycero-3-phosphocholine,98%(HPTLC) 98%(HPTLC)
  • Packaging:1G
  • Price:$ 134.4
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  • Manufacture/Brand:Chem-Impex
  • Product Description:1,2-Dioleoyl-sn-glycero-3-phosphocholine,≥98%(HPTLC) ≥98%(HPTLC)
  • Packaging:250MG
  • Price:$ 46.59
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  • Manufacture/Brand:Chem-Impex
  • Product Description:1,2-Dioleoyl-sn-glycero-3-phosphocholine,≥98%(HPTLC) ≥98%(HPTLC)
  • Packaging:5G
  • Price:$ 669.76
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  • Manufacture/Brand:Cayman Chemical
  • Product Description:1,2-Dioleoyl-sn-glycero-3-PC ≥98%
  • Packaging:5g
  • Price:$ 484
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  • Manufacture/Brand:Cayman Chemical
  • Product Description:1,2-Dioleoyl-sn-glycero-3-PC ≥98%
  • Packaging:500mg
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Relevant articles and documentsAll total 6 Articles be found

Preparation method of dioleoyl phosphatidylcholine

-

Paragraph 0030-0046, (2020/08/07)

The invention provides a method for artificially synthesizing dioleoyl phosphatidylcholine (DOPC), which comprises the following steps of: using glycerol phosphatidylcholine and oleic acid as raw materials to carry out a condensation reaction, pulping the obtained product, filtering, and recrystallizing to obtain high-purity dioleoyl phosphatidylcholine. The dioleoyl phosphatidylcholine (DOPC) prepared by the method disclosed by the invention can be used as a pharmaceutic adjuvant for various types of medicines such as injections, tablets, capsules and the like.

Synthesis of phosphatidylcholine: An improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine

Ichihara, Ken'ichi,Iwasaki, Hitomi,Ueda, Kaori,Takizawa, Ryoko,Naito, Hideko,Tomosugi, Mitsuhiro

, p. 94 - 99 (2007/10/03)

An improved safe method that does not contaminate the environment with cadmium chloride, a toxic heavy metal salt, was developed for the synthesis of phosphatidylcholine (PC). PC was synthesized from sn-glycero-3-phosphocholine (GPC) and fatty acid in one step under mild conditions without the use of cadmium chloride. GPC was prepared from egg yolk PC and adsorbed by kieselguhr in a Teflon vessel. The GPC on kieselguhr was acylated with fatty acid in the presence of two reagents, dicyclohexylcarbodiimide for synthesis of fatty acid anhydride and 4-dimethylaminopyridine as an acylating catalyst, at 30°C overnight. The PC thus produced was purified by silica gel column chromatography. The yield of dioleoyl PC was 90% based on the starting material, GPC.

cis-trans Isomerization of monounsaturated fatty acid residues in phospholipids by thiyl radicals

Chatgilialoglu, Chryssostomos,Ferreri, Carla,Ballestri, Marco,Mulazzani, Quinto G.,Landi, Laura

, p. 4593 - 4601 (2007/10/03)

Thiyl radicals reversibly attack the double bonds of methyl oleate and dioleoyl phosphatidyl choline (DOPC), thus producing methyl elaidate and the corresponding phospholipids containing trans-fatty acid residues in high yield. These processes are radical chain reactions with relatively long chain lengths. The rate constant for the β-elimination of a thiyl radical from the adduct radical has been estimated to be 6 x 106 s-1 at ambient temperature. The cis-trans isomerization of fatty acid residues in DOPC vesicles (multilamellar vesicles and large unilamellar vesicles made by the extrusion technique) by a thiyl radical, generated from biologically relevant thiols, has also been studied in detail. The presence of 0.2 mM oxygen does not influence the effectiveness of cis-trans isomerization in both homogeneous solution and lipid vesicles. This process, which does not cause lipid degradation but permanent modification of the membrane constituents, ultimately influences the barrier properties and functions of biological membranes.

A new approach to the stereospecific synthesis of phospholipids. The use of L-glyceric acid for the preparation of diacylglycerols, phosphatidylcholines, and related derivatives

Roodsari, Farzaneh S.,Wu, Dongpei,Pum, Gregory S.,Hajdu, Joseph

, p. 7727 - 7737 (2007/10/03)

A new stereospecific synthesis of phospholipid derivatives of 1,2- diacyl-sn-glycerols is reported. The synthesis is based on (1) the use of L- glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2- dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal ω-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.

The development of improved cationic lipids for gene transfer into cystic fibrosis airway epithelial cells

Harris,Marshall,Lee,Siegel,Mcneilly,Yew,Nietupski,Nichols,Cherry,Wan,Jiang,Lane,Rowe,Scheule,Smith,Cheng

, p. 289 - 292 (2007/10/03)

In an effort to improve the efficiency of cationic lipid mediated gene transfer, over 90 novel cationic lipids of diverse structural types were synthesized and evaluated in vitro. Four cationic lipids derived from phospholipids were examined. The most promising cationic lipid formulations were tested in vivo by intranasal or transtracheal instillation into the lungs of BALB/c mice. The most active formulations gave CAT reporter gene expression levels which are greater than 500 fold over that which could be attained using free DNA alone. Certain cationic lipid formulations have been shown to facilitate substantial expression of the CFTR (cystic fibrosis transmembrane conductance regulator) gene in vitro as determined by the SPQ and Ussing Chamber assays.

Process route upstream and downstream products

Process route

Conditions
Conditions Yield
With azobis(dimethylvaleronitrile); 2-hydroxyethanethiol; In tert-butyl alcohol; at 54 ℃; for 4h; Further Variations:; Reagents; Temperatures; Reaction partners; Product distribution;
L-glycero-3-phosphorylcholine
28319-77-9,563-24-6

L-glycero-3-phosphorylcholine

Tras-Elaidate sodium salt
18175-45-6

Tras-Elaidate sodium salt

Conditions
Conditions Yield
cis-Octadecenoic acid
112-80-1,2027-47-6

cis-Octadecenoic acid

L-glycero-3-phosphorylcholine
28319-77-9,563-24-6

L-glycero-3-phosphorylcholine

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

Conditions
Conditions Yield
With dmap; Hyflo Super-Cel; dicyclohexyl-carbodiimide; In chloroform; at 30 ℃;
90.3%
With dmap; dicyclohexyl-carbodiimide; In chloroform; at 20 ℃; for 12h; Reagent/catalyst; Solvent; Darkness;
82.33%
2-(1',2'-dioleoyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane

2-(1',2'-dioleoyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane

trimethylamine
75-50-3

trimethylamine

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

Conditions
Conditions Yield
With triethylamine; In acetonitrile; at 20 ℃; for 16h;
64%
1,2-dioleoyl-sn-glycerol
24529-88-2

1,2-dioleoyl-sn-glycerol

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 93 percent / Et3N / benzene / 16 h / 20 °C
2: 64 percent / Et3N / acetonitrile / 16 h / 20 °C
With triethylamine; In acetonitrile; benzene; 1: Substitution / 2: Ring cleavage;
Multi-step reaction with 2 steps
1: POCl3, Et3N / CHCl3 / 0.5 h / 0 °C
2: pyridine / CHCl3 / 14 h / Ambient temperature
With pyridine; triethylamine; trichlorophosphate; In chloroform;
trimethylamine
75-50-3

trimethylamine

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

Conditions
Conditions Yield
With benzene;
(Z)-(S)-3-(trityloxy)propane-1,2-diyl dioleate
22202-46-6

(Z)-(S)-3-(trityloxy)propane-1,2-diyl dioleate

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 73 percent / 12N HCl / CHCl3; methanol / 18 h / 0 °C
2: 93 percent / Et3N / benzene / 16 h / 20 °C
3: 64 percent / Et3N / acetonitrile / 16 h / 20 °C
With hydrogenchloride; triethylamine; In methanol; chloroform; acetonitrile; benzene; 1: Substitution / 2: Substitution / 3: Ring cleavage;
(S)-3-((4-methoxybenzyl)oxy)propane-1,2-diyl dioleate
143997-01-7

(S)-3-((4-methoxybenzyl)oxy)propane-1,2-diyl dioleate

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: dichlorodicyanobenzoquinone (DDQ) / CH2Cl2; H2O / 4 h / 20 °C
2: POCl3, Et3N / CHCl3 / 0.5 h / 0 °C
3: pyridine / CHCl3 / 14 h / Ambient temperature
With pyridine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trichlorophosphate; In dichloromethane; chloroform; water;
choline tosylate
55357-38-5

choline tosylate

C<sub>39</sub>H<sub>71</sub>Cl<sub>2</sub>O<sub>6</sub>P

C39H71Cl2O6P

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

Conditions
Conditions Yield
With pyridine; In chloroform; for 14h; Yield given; Ambient temperature;
choline
62-49-7

choline

1,2-dioleoyl-sn-glycero-3-phosphate sodium salt
108392-02-5

1,2-dioleoyl-sn-glycero-3-phosphate sodium salt

dioleoylphosphatidylcholine
4235-95-4

dioleoylphosphatidylcholine

Conditions
Conditions Yield
80%

Global suppliers and manufacturers

Global( 59) Suppliers
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  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Chemwill Asia Co., Ltd.
  • Business Type:Manufacturers
  • Contact Tel:021-51086038
  • Emails:chemwill_asia@126.com
  • Main Products:130
  • Country:China (Mainland)
  • Shanghai Upbio Tech Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-21-52196435
  • Emails:upbiocn@hotmail.com
  • Main Products:88
  • Country:China (Mainland)
  • Career Henan Chemical Co
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-371-86658258
  • Emails:purchase@coreychem.com
  • Main Products:137
  • Country:China (Mainland)
  • Chemlyte Solutions
  • Business Type:Other
  • Contact Tel:+86-189 8945 5137
  • Emails:sales@chemlytesolutions.com
  • Main Products:200
  • Country:China (Mainland)
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