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富马酸,反丁烯二酸

富马酸,反丁烯二酸用途

Fumaric acid,与烟酸酶缺乏症相关,是癌症引起的内源性代谢物。

富马酸,反丁烯二酸名称

[ CAS 号 ]:
110-17-8

[ 中文名 ]:
富马酸

[ 英文名 ]:
fumaric acid

[中文别名 ]:

[英文别名 ]:

U-1149
FEMA 2488
FUMARSAEURE
but-2-en-1,4-dioic acid
TMEDA
trans-2-Butenedioic Acid
Fumarsure
trans-butenedioic acid
Fumaric acid
fumaric

富马酸,反丁烯二酸生物活性

[ 描述 ]:

Fumaric acid,与烟酸酶缺乏症相关,是癌症引起的内源性代谢物。

[ 相关类别 ]:

天然产物 >> 酸和醛

研究领域 >> 癌症

研究领域 >> 代谢疾病

[ 靶点 ]

Human Endogenous Metabolite

[参考文献]

[1]. Whelan DT, et al. Fumaric aciduria: a new organic aciduria, associated with mental retardation and speech impairment. Clin Chim Acta. 1983 Aug 31;132(3):301-8.

[相关活性小分子]

富马酸,反丁烯二酸物理化学性质

[ 密度 ]:
1.5±0.1 g/cm3

[ 沸点 ]:
355.5±25.0 °C at 760 mmHg

[ 熔点 ]:
298-300 °C (subl.)(lit.)

[ 分子式 ]:
C₄H₄O₄

[ 分子量 ]:
116.072

[ 闪点 ]:
183.0±19.7 °C

[ 精确质量 ]:
116.010956

[ PSA ]:
74.60000

[ LogP ]:
-0.01

[ 外观性状 ]:
白色粉末或无色晶体

[ 蒸汽压 ]:
0.0±1.7 mmHg at 25°C

[ 折射率 ]:
1.526

[ 储存条件 ]:
室温

[ 稳定性 ]:
Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.

[ 水溶解性 ]:
0.63 g/100 mL (25 ºC)

富马酸,反丁烯二酸MSDS

富马酸,反丁烯二酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LS9625000

CHEMICAL NAME :: Fumaric acid

CAS REGISTRY NUMBER :: 110-17-8

BEILSTEIN REFERENCE NO. :: 0605763

LAST UPDATED :: 199710

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C4-H4-O4

MOLECULAR WEIGHT :: 116.08

WISWESSER LINE NOTATION :: QV1U1VQ -T

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9300 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 587 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes Liver - other changes Blood - hemorrhage

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6800 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - excitement Lungs, Thorax, or Respiration - respiratory stimulation

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

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

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - excitement Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5 gm/kg

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

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 40 mg/kg

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 77,750,1986 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 33940 No. of Facilities: 2317 (estimated) No. of Industries: 27 No. of Occupations: 44 No. of Employees: 30637 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 33940 No. of Facilities: 5692 (estimated) No. of Industries: 40 No. of Occupations: 58 No. of Employees: 136448 (estimated) No. of Female Employees: 48919 (estimated)

富马酸,反丁烯二酸安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H319

[ 警示性声明 ]:
P305 + P351 + P338

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36

[ 安全声明 (欧洲) ]:
S26

[ 危险品运输编码 ]:
UN 9126

[ WGK德国 ]:
1

[ RTECS号 ]:
LS9625000

[ 海关编码 ]:
2942000000

富马酸,反丁烯二酸合成路线

富马酸,反丁烯二酸上下游产品

富马酸,反丁烯二酸上游产品

富马酸,反丁烯二酸下游产品

富马酸,反丁烯二酸制备

一、用根霉菌属的绿状菌对糖类物质进行发酵，发酵完毕后，发酵液除去菌体及钙后，进行减压浓缩并调pH至酸性，可得粗结晶。粗结晶溶解，然后加入活性炭脱色，再进行结晶，过滤，即可得产品。

葡萄糖

根霉菌发酵中和加CaCO3发酵液加Na2SO4搅拌、过滤CaSO4、菌体滤液(钠盐)

减压蒸发浓缩液HCl过滤废液粗结晶→溶解活性炭脱色结晶过滤产品

(1)催化法　主要是在催化剂存在下将苯（或丁烯）氧化生成顺丁烯二酸（或顺丁烯二酸酐），再经异构化而得。

(2)糠醛法　以糠醛为原料，经氯酸钠氧化而得，其反应式如下：

将氯酸钠配成溶液，投入氧化罐中，加入五氧化二钒，加热至90～95℃，滴加糠醛，控制温度在105℃左右，加毕，在100℃保温2～3h，冷却结晶、过滤、干燥而得反丁烯二酸，收率62.7%。

(3)顺丁烯二酸法　以顺丁烯二酸为原料，经水解异构化制得，其反应式如下：

将顺酐用水吸收得35%左右的顺丁烯二酸水溶液，在95℃的温度下用活性炭脱色并去除焦油；然后在浓硫酸介质中用硫脲作催化剂，在85～95℃的温度下反应异构化生成反丁烯二酸；再经冷却、结晶、过滤、洗涤、离心、干燥后制得工业级反丁烯二酸。在上述工序中，将洗涤好的反丁烯二酸加入溶解锅中，加水煮沸充分溶解，经重结晶、过滤、洗涤、干燥，可制得食品级反丁烯二酸。

(4). 从水中得单斜的、菱形的针晶或叶状体。

(5). 烟草：FC，50， 54。

二、制法：

于装有搅拌器、回流冷凝器(连接溴化氢吸收装置)、滴液漏斗、温度计反应瓶中，加入预先干燥的丁二酸(2)118g（1.0mol），新蒸馏的三溴化磷^①212g，搅拌下滴加干燥的溴307g(98.5mL),约2h加完。滴加过程中体系变粘稠以至于难以搅拌。停止搅拌，加完所以的溴。放置过夜。水浴加热，搅拌4h，使溴的颜色消失(加热时不要使溴的蒸汽逸出)。将反应物慢慢倒入300mL沸水中，充分搅拌，析出晶体。再加入500mL水，加热至沸，使固体物溶解，过滤。冷却析晶。抽滤析出的晶体，水洗、干燥，得反丁烯二酸25～30g。母液减压浓缩至1/2体积时，冷却后又析出部分产品。共得反丁烯二酸(1)58g，收率50%。注：①三溴化磷可以用如下方法制备：于装有搅拌器、回流冷凝器(连接溴化氢吸收装置)、滴液漏斗、温度计的反应瓶中，加入红磷41g，二硫化碳250mL，于1.5h内滴加由干燥的溴326g(105mL)与200mL二硫化磷250g。三溴化磷的沸点为172.9℃。应将其保存于密闭的容器中。

三.制法：

将10g马来酸（2）置于反应瓶中，加入10mL水，几粒沸石，温热溶解后，加入20mL浓盐酸。装上回流冷凝器，加热回流0.5h。由热的溶液中很快析出结晶。冷却后抽滤，由1mol/L的稀盐酸中重结晶，得反丁烯二酸（1），mp286～287℃。

四.制法：

于装有搅拌器、温度计、回流冷凝器、滴液漏斗的反应瓶中，加入氯酸钠112.5g（1.06mol），水250mL，0.5g五氧化二钒，搅拌下加热至70～75℃。于滴液漏斗中加入50g（0.52mol）的糠醛（2），先滴加约4mL，以使反应剧烈发生。在保持反应剧烈进行的情况下加入其余糠醛，约30min加完。加完后于70～75℃继续反应5～6h。室温放置过夜。抽滤析出结晶，少量冷水洗涤，用约300mL（1mol/L）的盐酸重结晶，于100℃干燥，得反丁烯二酸（1）26g，mp282～284℃，收率43%。^[^3]

富马酸,反丁烯二酸海关

[ 海关编码 ]: 2942000000

富马酸,反丁烯二酸文献

A metabolic-based approach to improve xylose utilization for fumaric acid production from acid pretreated wheat bran by Rhizopus oryzae.

Bioresour. Technol. 180 , 119-27, (2015)

In this work, wheat bran (WB) was utilized as feedstock to synthesize fumaric acid by Rhizopus oryzae. Firstly, the pretreatment process of WB by dilute sulfuric acid hydrolysis undertaken at 100°C fo...

Physiology and pathophysiology of organic acids in cerebrospinal fluid.

J. Inherit. Metab. Dis. 16(4) , 648-69, (1993)

Concentrations of organic acids in cerebrospinal fluid (CSF) appear to be directly dependent upon their rate of production in the brain. There is evidence that the net release of short-chain monocarbo...

HMDB: a knowledgebase for the human metabolome.

Nucleic Acids Res. 37(Database issue) , D603-10, (2009)

The Human Metabolome Database (HMDB, http://www.hmdb.ca) is a richly annotated resource that is designed to address the broad needs of biochemists, clinical chemists, physicians, medical geneticists, ...

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