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石胆酸

石胆酸用途

Lithocholic acid是有毒的次级胆汁酸,能促使肝内胆汁淤积,能促进肿瘤发生。

石胆酸名称

[ CAS 号 ]:
434-13-9

[ 中文名 ]:
石胆酸

[ 英文名 ]:
Lithocholic acid

[中文别名 ]:

[英文别名 ]:

17b-(1-Methyl-3-carboxypropyl)etiocholan-3a-ol
(3α,5β)-3-Hydroxycholan-24-oic acid
5-β-Cholan-24-oic acid, 3-α-hydroxy-
3-α-Hydroxy-5-β-cholanic acid
EINECS 207-099-1
Cholan-24-oic acid, 3-hydroxy-, (3α,5β)-
4-10-00-00785 (Beilstein Handbook Reference)
5β-Cholanic Acid-3α-ol
Lithocholic acid
Lithocolic acid

石胆酸生物活性

[ 描述 ]:

Lithocholic acid是有毒的次级胆汁酸,能促使肝内胆汁淤积,能促进肿瘤发生。

[ 相关类别 ]:

信号通路 >> 自噬 >> 自噬

天然产物 >> 酸和醛

研究领域 >> 代谢疾病

[ 靶点 ]

Human Endogenous Metabolite

[参考文献]

[1]. Jenkins, D.J., et al., Effect on blood lipids of very high intakes of fiber in diets low in saturated fat and cholesterol. N Engl J Med, 1993. 329(1): p. 21-6.

[2]. Goldberg, A.A., et al., Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells. Oncotarget, 2011. 2(10): p. 761-82.

[3]. Matsubara, T., et al., TGF-beta-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. J Lipid Res, 2012. 53(12): p. 2698-707.

[4]. Yang R, et al. Metabolomic analysis of cholestatic liver damage in mice. Food Chem Toxicol. 2018 Jul 14;120:253-260.

[相关活性小分子]

石胆酸物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
511.0±23.0 °C at 760 mmHg

[ 熔点 ]:
183-188 °C(lit.)

[ 分子式 ]:
C₂₄H₄₀O₃

[ 分子量 ]:
376.573

[ 闪点 ]:
276.9±19.1 °C

[ 精确质量 ]:
376.297760

[ PSA ]:
57.53000

[ LogP ]:
6.70

[ 外观性状 ]:
固体;White to Almost white powder to crystaline

[ 蒸汽压 ]:
0.0±3.0 mmHg at 25°C

[ 折射率 ]:
1.528

[ 储存条件 ]:
Refrigerator

[ 水溶解性 ]:
水溶性：不溶；水溶解度：0.38 mg/l 25 °C；微溶：乙醇

石胆酸MSDS

石胆酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ2275000

CHEMICAL NAME :: 5-beta-Cholan-24-oic acid, 3-alpha-hydroxy-

CAS REGISTRY NUMBER :: 434-13-9

BEILSTEIN REFERENCE NO. :: 3217757

LAST UPDATED :: 199612

DATA ITEMS CITED :: 23

MOLECULAR FORMULA :: C24-H40-O3

MOLECULAR WEIGHT :: 376.64

WISWESSER LINE NOTATION :: L E5 B666TJ A E FY&2VQ OQ -B&AEFMO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3900 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 8800 mg/kg

SEX/DURATION :: female 0-21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 16 gm/kg

SEX/DURATION :: female 0-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - hepatobiliary system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 30160 ug/kg

SEX/DURATION :: female 12-19 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 37700 ug/kg

SEX/DURATION :: female 12-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intrauterine

DOSE :: 18850 ug/kg

SEX/DURATION :: female 5 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: Mutation test systems - not otherwise specified

MUTATION DATA

TYPE OF TEST :: DNA adduct

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 10 mg/L

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 15,1911,1994

石胆酸安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
F+

[ 安全声明 (欧洲) ]:
S22-S24/25

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

[ WGK德国 ]:
2

[ RTECS号 ]:
FZ2275000

石胆酸合成路线

石胆酸上下游产品

石胆酸上游产品

石胆酸下游产品

石胆酸文献

Ultra high resolution SFC-MS as a high throughput platform for metabolic phenotyping: application to metabolic profiling of rat and dog bile.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 966 , 200-7, (2014)

Ultra high resolution SFC-MS (on sub-2μm particles) coupled to mass spectrometry has been evaluated for the metabolic profiling of rat and dog bile. The selectivity of the SFC separation differed from...

Impact of confinement on proteins concentrated in lithocholic acid based organic nanotubes.

J. Colloid. Interface Sci. 454 , 97-104, (2015)

Organic nanotubes form in aqueous solution near physiological pH by self-assembly of lithocholic acid (LCA) with inner diameters of 20-40nm. The encapsulation of enhanced green fluorescent protein (eG...

Hydrogels Triggered by Metal Ions as Precursors of Network CuS for DNA Detection.

Chemistry 21 , 12194-201, (2015)

The gelation behavior of lithocholate (LC(-) ) with different metal ions in water was investigated. The microstructures of hydrogels were determined to be three-dimensional (3D) networks of fibrous ag...

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石胆酸