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丙二酸二甲酯

丙二酸二甲酯用途

丙二酸二甲酯是琥珀酸脱氢酶(SDH)的竞争性抑制剂。丙二酸二甲酯能够穿过血脑屏障并水解为丙二酸。丙二酸二甲酯减少神经元凋亡[1]。

丙二酸二甲酯名称

[ CAS 号 ]:
108-59-8

[ 中文名 ]:
丙二酸二甲酯

[ 英文名 ]:
Dimethyl malonate

[中文别名 ]:

[英文别名 ]:

dimethyl propanedioate
Propanedioic acid, dimethyl ester
Dimethyl malonate
MFCD00008460
Malonic acid dimethyl ester
methyl malonate
EINECS 203-597-8
Malonic acid, dimethyl ester

丙二酸二甲酯生物活性

[ 描述 ]:

丙二酸二甲酯是琥珀酸脱氢酶(SDH)的竞争性抑制剂。丙二酸二甲酯能够穿过血脑屏障并水解为丙二酸。丙二酸二甲酯减少神经元凋亡[1]。

[ 相关类别 ]:

信号通路 >> 细胞凋亡 >> 细胞凋亡

研究领域 >> 神经疾病

[体内研究]

丙二酸二甲酯(6 mg/kg/min；静脉输注；51 min)促进大鼠心脏骤停后的自主循环(ROSC)恢复和神经功能[1]。动物模型：Sprague Dawley雄性大鼠,心脏骤停模型[1]剂量：6 mg/kg/min给药：静脉输注,51 min结果：CA后ROSC改善。在CPR后第3天,预防神经功能下降并抑制海马神经元凋亡。CPR后第3天抑制caspase-3切割并增加HIF-1α表达。CPR后第3天降低氧化应激水平。再灌注45分钟后,抑制MMP过度超极化,抑制细胞色素C的泄漏。

[参考文献]

[1]. Xu J, et al. Inhibiting Succinate Dehydrogenase by Dimethyl Malonate Alleviates Brain Damage in a Rat Model of Cardiac Arrest. Neuroscience. 2018 Nov 21;393:24-32.

丙二酸二甲酯物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
177.1±8.0 °C at 760 mmHg

[ 熔点 ]:
−62 °C(lit.)

[ 分子式 ]:
C₅H₈O₄

[ 分子量 ]:
132.115

[ 闪点 ]:
90.0±0.0 °C

[ 精确质量 ]:
132.042252

[ PSA ]:
52.60000

[ LogP ]:
-0.36

[ 外观性状 ]:
液体

[ 蒸汽密度 ]:
>1 (vs air)

[ 蒸汽压 ]:
1.1±0.3 mmHg at 25°C

[ 折射率 ]:
1.402

[ 储存条件 ]:
室温

[ 稳定性 ]:
Stable. Incompatible with strong oxidizing agents. Flammable.

[ 水溶解性 ]:
negligible

丙二酸二甲酯MSDS

详细MSDS(安全技术说明书)

丙二酸二甲酯毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OO0950000

CHEMICAL NAME :: Malonic acid, dimethyl ester

CAS REGISTRY NUMBER :: 108-59-8

LAST UPDATED :: 199709

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C5-H8-O4

MOLECULAR WEIGHT :: 132.13

WISWESSER LINE NOTATION :: 1OV1VO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,363,1979 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5331 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,363,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,363,1979

丙二酸二甲酯安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315-H319-H335

[ 警示性声明 ]:
P261-P305 + P351 + P338

[ 个人防护装备 ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S26-S36

[ WGK德国 ]:
1

[ RTECS号 ]:
OO0950000

[ 海关编码 ]:
29171910

丙二酸二甲酯合成路线

详细合成路线

丙二酸二甲酯上下游产品

丙二酸二甲酯上游产品

丙二酸二甲酯下游产品

丙二酸二甲酯制备

多用氰化酯化法。氯乙酸与碳酸钠中和生成氯乙酸钠，再用氰化钠进行氰化得氰乙酸钠。氰乙酸钠水解成丙二酸钠，然后在硫酸存在下与甲醇酯化得丙二酸二甲酯，经洗涤、蒸馏即得成品。工业品含酯量≥98%。原料消耗定额：氯乙酸1120kg/t、氰化钠551kg/t、甲醇955kg/t。国外开发的新工艺主要以催化羰基化法为主，即以氯乙酸酯、一氧化碳、甲醇为原料，在催化剂存在下，一步反应合成丙二酸二甲酯。相比之下，催化羰基化法工艺技术先进，但工艺复杂，反应条件苛刻，工业化实现有一定的困难。

丙二酸二甲酯海关

[ 海关编码 ]: 2917190090

[ 中文概述 ]:
2917190090 其他无环多元羧酸. 增值税率:17.0% 退税率:9.0% 监管条件:无最惠国关税:6.5% 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 对苯二甲酸请注明4-CBA值, 对苯二甲酸请注明P-TL酸值, 对苯二甲酸请注明色度, 对苯二甲酸请注明水分

[ Summary ]:
2917190090 acyclic polycarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

丙二酸二甲酯文献

Characterization of the cardiac succinylome and its role in ischemia-reperfusion injury.

J. Mol. Cell. Cardiol. 88 , 73-81, (2015)

Succinylation refers to modification of lysine residues with succinyl groups donated by succinyl-CoA. Sirtuin5 (Sirt5) is a mitochondrial NAD(+)-dependent deacylase that catalyzes the removal of succi...

Enantioselective modular synthesis of 2,4-disubstituted cyclopentenones by iridium-catalyzed allylic alkylation.

Angew. Chem. Int. Ed. Engl. 45(15) , 2466-9, (2006)

A rapid method for the synthesis of methylmalonyl-coenzyme A and other CoA-esters.

Anal. Biochem. 214(1) , 318-20, (1993)

A rapid and high-yield synthesis of methylmalonyl coenzyme A is reported. The two-step procedure involves preparation of the thiophenyl ester of methylmalonic acid using dicyclohexylcarbodiimide as a ...

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