白屈菜酸

白屈菜酸用途

Chelidonic acid 是从 Chelidonium majus L. 中分到的酸类物质,为一种温和镇痛剂、抗菌剂和中枢神经系统镇静剂。Chelidonic acid 具有抗炎作用,可能通过抑制 NF-κB 和 caspase-1 来降低 IL-6 的产生。Chelidonic acid 为 glutamate decarboxylase 抑制剂,Ki 值为 1.2 μM。

白屈菜酸名称

[ CAS 号 ]:
99-32-1

[ 中文名 ]:
白屈菜酸

[ 英文名 ]:
Chelidonic acid

[中文别名 ]:

[英文别名 ]:

4-oxopyran-2,6-dicarboxylic acid
EINECS 202-749-0
MFCD00006577

白屈菜酸生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 细胞凋亡 >> 胱天蛋白酶

研究领域 >> 炎症/免疫

[ 靶点 ]

NF-κB

Caspase-1

Glutamate decarboxylase:1.2 μM (Ki)

[体外研究]

白屈菜酸剂量依赖性地降低0.1-10μM的IL-6产生,抑制IL-6 mRNA在1-10μM时的表达[1]。白屈菜酸(0.1-10μM)可降低caspase-1活化,核内NF-κB活化,并增加细胞质NF-κB的活化[1]。白屈菜酸是谷氨酸脱羧酶抑制剂,Ki为1.2μM。白屈菜酸不会促进脱辅酶的形成或与游离的吡哆醛-P反应[2]。

[体内研究]

白屈菜酸(0.2,2 mg/kg口服)可减轻小鼠卵清蛋白诱导的过敏反应[3]。

[参考文献]

[1]. Shin HJ, et al. Inhibitory effects of chelidonic acid on IL-6 production by blocking NF-κB and caspase-1 in HMC-1 cells. Immunopharmacol Immunotoxicol. 2011 Dec;33(4):614-9.

[2]. Porter TG, et al. Chelidonic acid and other conformationally restricted substrate analogues as inhibitors of rat brain glutamate decarboxylase. Biochem Pharmacol. 1985 Dec 1;34(23):4145-50.

[3]. Oh HA, et al. Beneficial effects of chelidonic acid on a model of allergic rhinitis. Send to Int Immunopharmacol. 2011 Jan;11(1):39-45.

白屈菜酸物理化学性质

[ 密度 ]:
1.821 g/cm3

[ 沸点 ]:
471.3ºC at 760 mmHg

[ 熔点 ]:
265 °C (dec.)(lit.)

[ 分子式 ]:
C₇H₄O₆

[ 分子量 ]:
184.10

[ 闪点 ]:
204.1ºC

[ 精确质量 ]:
184.00100

[ PSA ]:
104.81000

[ LogP ]:
0.03620

[ 储存条件 ]:
2-8°C

白屈菜酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UP7350000

CHEMICAL NAME :: 4H-Pyran-2,6-dicarboxylic acid, 4-oxo-

CAS REGISTRY NUMBER :: 99-32-1

BEILSTEIN REFERENCE NO. :: 0163607

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C7-H4-O6

MOLECULAR WEIGHT :: 184.11

WISWESSER LINE NOTATION :: T6O DVJ BVQ FVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

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

REFERENCE :: CBCCT* "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. (National Academy of Science Library, 2101 Constitution Ave., NW, Washington, DC 20418) Volume(issue)/page/year: 6,54,1954

白屈菜酸安全信息

[ 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 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xi: Irritant;

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S26-S36

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
UP7350000

[ 海关编码 ]:
2932999099

白屈菜酸合成路线

详细合成路线

白屈菜酸上下游产品

白屈菜酸上游产品

白屈菜酸下游产品

白屈菜酸制备

由草酸二乙酯和丙酮反应得到。

白屈菜酸海关

[ 海关编码 ]: 2932999099

[ 中文概述 ]:
2932999099. 其他仅含氧杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

白屈菜酸文献

Chelidonic acid and other conformationally restricted substrate analogues as inhibitors of rat brain glutamate decarboxylase.

Biochem. Pharmacol. 34 , 4145-4150, (1985)

Twenty conformationally restricted analogues of glutamate including benzoic acids, hydroxy-benzoic acids, pyridine dicarboxylic acids, and pyran dicarboxylic acids were tested as inhibitors of glutama...

Purification and characterization of dihydrodipicolinate synthase from pea.

Plant Physiol. 98(3) , 813-821., (1992)

Dihydrodipicolinate synthase (EC 4.2.1.52), the first enzyme unique to lysine biosynthesis in bacteria and higher plants, has been purified to homogeneity from etiolated pea (Pisum sativum) seedlings ...

Tracer studies with 13C-labeled carbohydrates in cultured plant cells. Retrobiosynthetic analysis of chelidonic acid biosynthesis.

Phytochemistry 57(1) , 33-42, (2001)

The biosynthesis of chelidonic acid was studied in cell suspension cultures of Leucojum aestivum. Cell cultures were supplied with [U-13C]glucose, [l-13C]glucose or [U-13Cs]ribose/ribulose in standard...

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