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香豆素

香豆素用途

Coumarin 是中国北沙参中主要的生物活性成分,具有抗癌,抗炎,抗病毒等多种药理活性。

香豆素名称

[ CAS 号 ]:
91-64-5

[ 中文名 ]:
香豆素

[ 英文名 ]:
Coumarin

[中文别名 ]:

[英文别名 ]:

MFCD00006850
Kumarin
EINECS 202-086-7
Rattex
CUMARIN
chromen-2-one
COUMARINE
Coumarin

香豆素生物活性

[ 描述 ]:

Coumarin 是中国北沙参中主要的生物活性成分,具有抗癌,抗炎,抗病毒等多种药理活性。

[ 相关类别 ]:

信号通路 >> 其他 >> 其他

研究领域 >> 炎症/免疫

研究领域 >> 癌症

研究领域 >> 感染

天然产物 >> 苯丙酸类

[参考文献]

[1]. Liu M, et al. Quantitative analysis of nine coumarins in rat urine and bile after oral administration of Radix Glehniae extract by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. Biomed Chromatogr. 2011 Jul;25(7):783-93.

[相关活性小分子]

香豆素物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
298.0±0.0 °C at 760 mmHg

[ 熔点 ]:
68-73 °C(lit.)

[ 分子式 ]:
C₉H₆O₂

[ 分子量 ]:
146.143

[ 闪点 ]:
118.3±16.1 °C

[ 精确质量 ]:
146.036774

[ PSA ]:
30.21000

[ LogP ]:
1.39

[ 外观性状 ]:
白色结晶固体

[ 蒸汽压 ]:
0.0±0.6 mmHg at 25°C

[ 折射率 ]:
1.595

[ 储存条件 ]:
库房低温,通风,干燥,与食品原料分开存放

[ 水溶解性 ]:
1.7 g/L (20 ºC)

香豆素MSDS

详细MSDS(安全技术说明书)

香豆素毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GN4200000

CHEMICAL NAME :: Coumarin

CAS REGISTRY NUMBER :: 91-64-5

BEILSTEIN REFERENCE NO. :: 0383644

LAST UPDATED :: 199710

DATA ITEMS CITED :: 36

MOLECULAR FORMULA :: C9-H6-O2

MOLECULAR WEIGHT :: 146.15

WISWESSER LINE NOTATION :: T66 BOVJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 87 mg/kg/17W-I

TOXIC EFFECTS :: Liver - liver function tests impaired

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 30 mg/kg/30D-I

TOXIC EFFECTS :: Liver - liver function tests impaired

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 293 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 :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 196 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 220 mg/kg

TOXIC EFFECTS :: Behavioral - analgesia Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 242 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 :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 202 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Liver - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1400 mg/kg/7D-I

TOXIC EFFECTS :: Liver - changes in liver weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4800 mg/kg/16D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9750 mg/kg/13W-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), zonal Blood - changes in erythrocyte (RBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 88 gm/kg/42W-C

TOXIC EFFECTS :: Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other transferases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3600 mg/kg/16D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 9750 mg/kg/13W-I

TOXIC EFFECTS :: Liver - changes in liver weight Blood - normocytic anemia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1900 mg/kg/19D-I

TOXIC EFFECTS :: Liver - jaundice, other or unclassified Blood - hemorrhage Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 109 gm/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 18025 mg/kg/2Y-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 144 gm/kg/2Y-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - bronchiogenic carcinoma

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 200 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3600 mg/kg

SEX/DURATION :: female 6-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 20 mmol/L

REFERENCE :: PNASA6 Proceedings of the National Academy of Sciences of the United States of America. (National Academy of Sciences, Printing & Pub. Office, 2101 Constitution Ave., Washington, DC 20418) V.1- 1915- Volume(issue)/page/year: 48,686,1962 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,113,1976 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,113,1976 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW PMDCAY Progress in Medical Chemistry. (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.1- 1961- Volume(issue)/page/year: 10,85,1974 TOXICOLOGY REVIEW MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 47,161,1978 TOXICOLOGY REVIEW FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,277,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 20340 No. of Facilities: 379 (estimated) No. of Industries: 14 No. of Occupations: 39 No. of Employees: 31272 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 20340 No. of Facilities: 16304 (estimated) No. of Industries: 113 No. of Occupations: 99 No. of Employees: 239705 (estimated) No. of Female Employees: 110313 (estimated)

香豆素安全信息

[ 符号 ]:

GHS06

[ 信号词 ]:
Danger

[ 危害声明 ]:
H301

[ 警示性声明 ]:
P301 + P310

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

[ 危害码 (欧洲) ]:
Xn:Harmful

[ 风险声明 (欧洲) ]:
R20/21/22;R36/37/38;R40

[ 安全声明 (欧洲) ]:
S36-S36/37-S26

[ 危险品运输编码 ]:
UN 2811 6.1/PG 3

[ WGK德国 ]:
1

[ RTECS号 ]:
GN4200000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1

[ 海关编码 ]:
2932999099

香豆素合成路线

详细合成路线

香豆素上下游产品

香豆素上游产品

香豆素下游产品

香豆素制备

1.由水杨醛经珀金（Perkin）反应制得。这是珀金在1868年最初采用的合成方法。水杨醛与乙酐反应可以使用煅烧的碳酸钾作为催化剂。将碳酸、乙酐加入水杨醛中，加热至187℃，在气相温度约120℃时蒸出乙酸，然后再加入乙酐，在210-212℃进行反应。得到的香豆素粗品用水洗涤，再真空蒸馏。然后用乙醇或异丙醇重结晶，在50℃干燥得成品。

由邻甲酚与磷酰氯作用，得到中间体邻甲酚磷酸酯，并在180℃氯化，将甲基变为-CHCI2，然后再在160-180℃与醋酸钠作用5h进行环化即得。如果邻甲酚与光气作用，则经由中间体邻甲酚碳酸酯而完成这一工艺过程：邻甲酚钠盐与光气在60℃、0.15MPa下反应生成邻甲酚碳酸酯。用氯气在180-185℃将酯化进行氯化，至含氯量约为37%，相当于每个甲酚的侧链上含有两个氯原子。最后，在吡啶或氧化锌和氧化钴存在下，与乙酸和乙酐缩合，反应得到香豆素，该法收率相当高。

3. 烟草：BU，14。

香豆素海关

[ 海关编码 ]: 2932201000

[ 中文概述 ]:
HS:2932201000 香豆素、甲基香豆素及乙基香豆素增值税率:17.0% 退税率:13.0% 监管条件:无最低关税:6.5% 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
HS:2932201000 2h-chromen-2-one VAT:17.0% Tax rebate rate:13.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

香豆素文献

Proteasome functioning in breast cancer: connection with clinical-pathological factors.

PLoS ONE 9(10) , e109933, (2014)

Breast cancer is one of four oncology diseases that are most widespread in the world. Moreover, breast cancer is one of leading causes of cancer-related deaths in female population within economically...

Mitochondrial targeting of bilirubin regulatory enzymes: An adaptive response to oxidative stress.

Toxicol. Appl. Pharmacol. 282(1) , 77-89, (2015)

The intracellular level of bilirubin (BR), an endogenous antioxidant that is cytotoxic at high concentrations, is tightly controlled within the optimal therapeutic range. We have recently described a ...

Pre-clinical evaluation of AZD-2014, a novel mTORC1/2 dual inhibitor, against renal cell carcinoma.

Cancer Lett. 357(2) , 468-75, (2015)

Here we found that dual mTORC1/2 inhibitor AZD-2014 significantly inhibited RCC cell survival and growth, with higher efficiency than conventional mTORC1 inhibitors rapamycin and RAD001. RCC cell apop...

更多文献

香豆素