15441-06-2|Dimethyl 3,3-Dithiodipropionate| Ambeed

Abstract: Cerebral aneurysms are a source of neurological morbidity and mortality, most often as a result of rupture. The most common approach for treating aneurysms involves endovascular embolization using nonbiodegradable medical devices, such as coils. However, the need for retreatment due to the recanalization of coil-treated aneurysms highlights the importance of exploring alternative solutions. In this study, we propose an injectable extracellular matrix derived embolic formed in situ by Michael addition of gelatin-thiol (Gel-SH) and hyaluronic acid vinyl (HA-VS) that may be delivered with a therapeutic agent (here, RADA-SP) to fill and remodel aneurysmal tissue without leaving behind permanent foreign bodies. The injectable embolic material demonstrated rapid gelation under physiological conditions, forming a highly porous structure and allowing for cellular infiltration. The injectable embolic exhibited thrombogenic behavior in vitro that was comparable to that of alginate injectables. Furthermore, in vivo studies in a murine carotid aneurysm model demonstrated the successful embolization of a saccular aneurysm and extensive cellular infiltration both with and without RADA-SP at 3 weeks, with some evidence of increased vascular or fibrosis markers with RADA-SP incorporation. The results indicate that the developed embolic has inherent potential for acutely filling cerebrovascular aneurysms and encouraging the cellular infiltration that would be necessary for stable, chronic remodeling.

Purchased from AmBeed: 15441-06-2

Product Details of [ 15441-06-2 ]

CAS No. :	15441-06-2
Formula :	C₈H₁₄O₄S₂
M.W :	238.32
SMILES Code :	O=C(OC)CCSSCCC(OC)=O
MDL No. :	MFCD00128218
InChI Key :	OSZKBWPMEPEYFU-UHFFFAOYSA-N
Pubchem ID :	84913

Safety of [ 15441-06-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 15441-06-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 15441-06-2 ]

[ 15441-06-2 ] Synthesis Path-Downstream 1~51

1
[ 67-56-1 ]
[ 1119-62-6 ]
[ 15441-06-2 ]

References: [1]Journal of Polymer Science,1955,vol. 17,p. 221,233.
[2]Journal of Polymer Science,1955,vol. 17,p. 221,233.
[3]Journal of Organic Chemistry,1973,vol. 38,p. 937 - 939.
[4]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3277 - 3287.
[5]Biomacromolecules,2019,vol. 20,p. 1412 - 1420.

2
[ 624-92-0 ]
[ 15441-06-2 ]
3-methyldisulfanylpropionic acid methyl ester [ No CAS ]

References: [1]Patent: US2719170,1954, .

3
[ 15441-06-2 ]
[ 50906-77-9 ]

References: [1]Chemical Communications,2008,p. 5301 - 5303.
[2]Soft Matter,2018,vol. 14,p. 6678 - 6683.
[3]Annales de Chimie (Cachan, France),1958,vol. <13>3,p. 599,631.
[4]Biomacromolecules,2019,vol. 20,p. 1412 - 1420.

4
[ 6291-62-9 ]
[ 15441-06-2 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1983,vol. 32,p. 553 - 555.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1983,p. 613 - 616.
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1973,vol. 22,p. 220 - 222.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1973,vol. 22,p. 209 - 212.

5
[ 15441-06-2 ]
[ 109-76-2 ]
[ 37818-76-1 ]

References: [1]Journal of Organic Chemistry,1973,vol. 38,p. 937 - 939.

6
[ 292638-85-8 ]
[ 15441-06-2 ]

Yield	Reaction Conditions	Operation in experiment
89.3%		In a 500ml three neck flask equipped with a stirrer, a condenser and a thermometer, 200ml 10 percent (percentage by weight, hereinafter is the same)NaHCO3 solution and 21.7g(0.25mol) methyl acrylate were added sequentially, then the system was cooled to -5-10°C. Keeping under the temperature, a cooling sodium polysulphide (0.19 mol, counted by Na2S) solution was dropped during 0.5-2 hours. After the dropwise addition, ice water bath was removed. The mixture was left standing under the room temperature for 5-6 hours. Then the reaction was over. The obtained mixture was allowed to stand and separate into two layers. The water layer was removed. A 120ml (1 mol / L) Na2SO3 solution was added to the oil layer. The mixture then reacted continuously for 2-5 hours under the temperature of 50°C until the reaction was over. The resulting mixture was again allowed to stand and separate into layers. Then the water layer was removed, and the oil layer was washed with water. 26.8g light yellow oily substance was obtained by vacuum distilling, the yield is 89.3percent, the boiling point is 182-185°C / 7mmHg.
	With hydrogen sulfide; sulfur; methylamine; In water; at 15 - 25℃;	129 g (1.5 moles) of methyl acrylate was added to a 1 L four-necked flask equipped with a thermometer and a stirrer,40percent methylamine aqueous solution 5.2g, sulfur 90g, temperature control 15-25 30.1g hydrogen sulfide gas,To give a pale yellow reaction mixture;

References: [1]Patent: EP1810966,2007,A1 .Location in patent: Page/Page column 3.
[2]Journal of Organic Chemistry,1970,vol. 35,p. 2994 - 3002.
[3]Patent: CN104961705,2017,B .Location in patent: Paragraph 0036; 0037; 0038.

7
[ 15441-06-2 ]
[ 868-85-9 ]
[ 70550-09-3 ]

References: [1]Journal of Organic Chemistry,1979,vol. 44,p. 2938 - 2941.

8
[ 15441-06-2 ]
[ 762-04-9 ]
[ 70550-10-6 ]

References: [1]Journal of Organic Chemistry,1979,vol. 44,p. 2938 - 2941.

9
[ 15441-06-2 ]
[ 74-89-5 ]
[ 999-72-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium sulfite; In water; at 10℃; for 24h;Inert atmosphere;Product distribution / selectivity;	Example 24; Into a 4-necked 8 L flask equipped with an agitator, a thermometer, a gas dispersion tube, a nitrogen purging adapter, and a cooling jacket, 3,3'-dithioproionic acid methyl ester (944 g, 4 mol) was introduced. As the reaction solvent, 1000 g of water was introduced. 30 g of sodium sulfite (Na2SO3) was introduced, and the mixture was agitated to dissolve it. While maintaining the reaction temperature at 10° C., monomethylamine (99percent, 378 g, 12 mol) was added through the gas dispersion tube over about 4 hours. After completing introduction of monomethylamine, the mixture was stirred for 20 hours, and stirred while maintaining the inside temperature at 10° C. to complete the reaction. At this time, excessive monomethylamine and formed methanol were distilled and removed under vacuum. To crystallize the produced DDDA, the temperature of the reaction solution was lowered to 0° C., and then it was stirred for 100 minutes. To filter the formed solid, the solid was dehydrated using a laboratory centrifugal filter (r=0.4 m, rpm=1700). Subsequently, the dehydrated solid was completely dried using a vacuum oven drier, and then the final weight was measured. The content of remaining MMAP impurity in the dried DDDA was quantitatively analyzed and the result is described in the following Table 5.
	In methanol; at 5 - 15℃; for 24h;	The above reaction mixture was added with 100 g of methanol and 55 g (1.77 mol) of methylamine gas was added under stirring at a temperature of 5-15 ° C,Add insulation for 24 hours,To give a methanol suspension of N, N'-dimethyl-3,3'-dithiodipropionamide.Steam distillation at least atmospheric distillation of methanol, evaporated to no liquid and then vacuum distillation, until the kettle temperature reached 70 , the pressure reached -0.09Mpa not flow so far;Kettle by adding ethyl acetate 150g, continue to distillation to the kettle temperature to 80 , the pressure reached -0.09Mpa no flow so far,Then, 300 g of ethyl acetate was added to the kettle to form a suspension of the amidated product in ethyl acetate;

References: [1]Patent: US2012/330061,2012,A1 .Location in patent: Page/Page column 7.
[2]Journal of Heterocyclic Chemistry,1971,vol. 8,p. 581 - 586.
[3]Patent: CN104961705,2017,B .Location in patent: Paragraph 0036; 0039; 0040.

10
[ 2637-34-5 ]
C₁₀H₁₈N₂O₆S [ No CAS ]
[ 2127-03-9 ]
[ 15441-06-2 ]
[ 119023-07-3 ]

References: [1]Bulletin des Societes Chimiques Belges,1988,vol. 97,p. 535 - 540.

11
[ 1121-30-8 ]
3-Chlorooxalylsulfanyl-propionic acid methyl ester [ No CAS ]
[ 15441-06-2 ]
[ 119023-07-3 ]

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 57 - 67.

12
[ 15441-06-2 ]
[ 65505-76-2 ]
[ 951-78-0 ]
[ 118042-44-7 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 5598 - 5602.

13
[ 15441-06-2 ]
[ 65505-76-2 ]
[ 118042-44-7 ]

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 374 - 375.

14
[ 15441-06-2 ]
[ 41345-74-8 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 4933 - 4936.
[2]Journal of Organic Chemistry,2000,vol. 65,p. 3123 - 3125.

15
[ 67-56-1 ]
[ 107-96-0 ]
[ 15441-06-2 ]

References: [1]Canadian Journal of Chemistry,1988,vol. 66,p. 3070 - 3076.

16
[ 120-72-9 ]
[ 15441-06-2 ]
[ 158585-49-0 ]