当归内酯; 4-羟基-3-戊烯酸内酯; 5-甲基-2(3H)-呋喃酮

用途

α-Angelica lactone 是一种天然存在的抗癌剂,也是一种乙烯基亲核试剂。α-Angelica lactone 可以得到手性的 δ-氨基 γ,γ-二取代丁烯醇内酯羰基衍生物,并在 γ-碳上表现出亲电子俘获。α-Angelica lactone 通过选择性增强谷胱甘肽-S-硫转移酶 (GST) 和 UDP-葡糖苷转移酶 (UGT) 解毒酶发挥强大的化学保护作用。

名称

[ CAS 号 ]:
591-12-8

[ 中文名 ]:
当归内酯

[ 英文名 ]:
Alpha-Angelica lactone

[中文别名 ]:

[英文别名 ]:

D2-Angelica lactone
δ2-Angelica lactone
EINECS 209-701-8
5-methyl-3H-furan-2-one
α-Angelica lactone
2(3H)-Furanone, 5-methyl-
5-Methylfuran-2(3H)-one
g-Methyl-b,g-crotonolactone
alpha-Angelica lactone
MFCD00005375

生物活性

[ 描述 ]:

[ 相关类别 ]:

研究领域 >> 癌症

信号通路 >> 代谢酶/蛋白酶 >> 谷胱甘肽S-转移酶

[ 靶点 ]

Glutathione-S-thansferase (GST) detoxification enzyme[1][2] UDP-glucononosyltransferase (UGT) detoxification enzyme[2]

[参考文献]

[1]. W A Nijhoff, et al. Quantification of Induction of Rat Oesophageal, Gastric and Pancreatic Glutathione and Glutathione S-transferases by Dietary Anticarcinogens. Carcinogenesis. 1994 Sep;15(9):1769-72.

[2]. E M J van der Logt, et al. Induction of Rat Hepatic and Intestinal UDP-glucuronosyltransferases by Naturally Occurring Dietary Anticarcinogens. Carcinogenesis. 2003 Oct;24(10):1651-6.

[3]. Lin Zhou, et al. Catalytic Asymmetric Vinylogous Mannich-type (AVM) Reaction of Nonactivated α-Angelica Lactone. Org Lett. 2011 Jun 17;13(12):3056-9.

[4]. Jessica A Griswold, et al. Diastereoselective Organocatalytic Addition of α-Angelica Lactone to β-Halo-α-ketoesters. J Org Chem. 2017 Feb 17;82(4):2276-2280.

物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
249.4±9.0 °C at 760 mmHg

[ 熔点 ]:
13-17 °C(lit.)

[ 分子式 ]:
C₅H₆O₂

[ 分子量 ]:
98.100

[ 闪点 ]:
68.3±0.0 °C

[ 精确质量 ]:
98.036781

[ PSA ]:
26.30000

[ LogP ]:
0.84

[ 外观性状 ]:
淡黄色至绿色液体

[ 蒸汽压 ]:
0.0±0.5 mmHg at 25°C

[ 折射率 ]:
1.472

[ 储存条件 ]:
库房通风低温干燥,与氧化剂、食品添加剂分开存放

[ 水溶解性 ]:
5 g/100 mL (25 ºC)

MSDS

毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LU5075000

CHEMICAL NAME :: 2(3H)-Furanone, 5-methyl-

CAS REGISTRY NUMBER :: 591-12-8

BEILSTEIN REFERENCE NO. :: 0108394

LAST UPDATED :: 199710

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C5-H6-O2

MOLECULAR WEIGHT :: 98.11

WISWESSER LINE NOTATION :: T5OV CHJ E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3900 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0571138

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2800 mg/kg

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

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 3,249,1980

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

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

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 2,109,1946

安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ 危害码 (欧洲) ]:
Xi

[ 安全声明 (欧洲) ]:
S24/25

[ 危险品运输编码 ]:
NA 1993 / PGIII

[ WGK德国 ]:
2

[ RTECS号 ]:
LU5075000

[ 海关编码 ]:
2932209090

合成路线

上下游产品

上游产品

下游产品

制备

1. 合成方法较多，常见者以水杨醛为基本原料，通过铂金(perkin)反应而制备。

2. 烟草：FC，6， 18。当归内酯由乙酰丙酸的干馏得到。

海关

[ 海关编码 ]: 2932209090

[ 中文概述 ]:
2932209090. 其他内酯. 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 ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

文献

Characterization of the PON1 active site using modeling simulation, in relation to PON1 lactonase activity

Bioorg. Med. Chem. 16 , 7504-9, (2008)

Paraoxonase1 (PON1) is a HDL bound enzyme and many of the anti-atherogenic properties of HDL are attributed to PON1. The enzyme precise mechanism of protective action and its endogenous substrate rema...

Enhancement of rat hepatic and gastrointestinal glutathione and glutathione S-transferases by alpha-angelicalactone and flavone.

Carcinogenesis 16(3) , 607-12, (1995)

The naturally occurring anticarcinogens flavone and alpha-angelicalactone incorporated separately and simultaneously in the diet at 0.5, 0.1, 0.05 and 0.01% w/w, were studied with respect to their eff...

Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone.

Org. Lett. 13(12) , 3056-9, (2011)

A direct highly diastereo- and enantioselective asymmetric vinylogous Mannich-type (AVM) reaction of aldimines with nonactivated natural α-angelica lactone has been successfully developed. It was demo...

更多文献

当归内酯; 4-羟基-3-戊烯酸内酯; 5-甲基-2(3H)-呋喃酮

用途

名称

生物活性

物理化学性质

MSDS

详细MSDS(安全技术说明书)

毒性和生态

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

安全信息

合成路线

详细合成路线

上下游产品

上游产品

下游产品

制备

海关

文献

相关化工产品/化学物质：

相关药品：

推荐生产厂家/供应商：

热门化合物