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434-13-9

434-13-9 structure
434-13-9 structure
  • Name: Lithocholic acid
  • Chemical Name: lithocholic acid
  • CAS Number: 434-13-9
  • Molecular Formula: C24H40O3
  • Molecular Weight: 376.573
  • Catalog: API Digestive system medication Biliary medicine
  • Create Date: 2018-05-10 08:00:00
  • Modify Date: 2026-07-01 13:30:43
  • Lithocholic acid is a toxic secondary bile acid, causes intrahepatic cholestasis, has tumor-promoting activity.Target: OthersLithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. It has also been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ. It has been implicated in human and experimental animal carcinogenesis. Preliminary in vitro research suggests that LCA selectively kills neuroblastoma cells, while sparing normal neuronal cells and is cytotoxic to numerous other malignant cell types at physiologically relevant concentrations.
Name lithocholic acid
Synonyms Ursodeoxycholic Acid Impurity 3（Ursodeoxycholic Acid Impurity C）
3-α-Hydroxy-5-β-cholanic acid
3ALPHA-HYDROXYCHOLANIC ACID
Ursodeoxycholic Acid Impurity C -9
3alpha-hydroxy-5beta-cholanoicacid
5beta-Cholanic Acid-3alpha-ol 3alpha-Hydroxy-5beta-cholanic Acid
LITHOCHOLIC ACID >=
BETA-CHOLANIC ACID-3-ALPHA-OL
3-hydroxy-,(3alpha,5beta)-cholan-24-oicaci
3-Hydroxycholan-24-oic acid
Lithocholic acid, R
17-beta-(1-Methyl-3-cboxypropyl)ethiocholan-3-alpha-ol
3alpha-hydroxy-5beta-cholan-24-oicaci
17β-(1-Methyl-3-c-boxypropyl) etiocholan-3α-ol
3α-Hydroxy-5β-cholanoic Acid
3-hydroxycholan-24-oicacid
Chenodeoxycholic Acid Impurity 3
17beta-(1-methyl-3-cboxypropyl)etiocholan-3alpha-ol
3α-Hydroxy-5β-cholanic acid
(3α,5β)-3-Hydroxycholan-24-oic acid
3alpha-Hydroxy-5beta-cholanoic acid
Stone cholic acid
Chenodeoxycholic acid Impurity C
EINECS 207-099-1
NCI-CO-3861
3-hydroxy-,(3-alpha,5-beta)-cholan-24-oicaci
3α-Hydroxy-5β-cholanic Acid
MFCD00003682
5-beta-Cholanic acid, 3-alpha-hydroxy
3a-Hydroxycholanic Acid
3a-Hydroxy-5b-cholan-24-oic Acid
Cholan-24-oic acid, 3-hydroxy-, (3-α,5-β)- (9CI)
Cholan-24-oic acid, 3-hydroxy-, (3alpha,5beta)
LITHOCHOLIC ACID(RG)
Lithocholic acid CRS
17b-(1-Methyl-3-carboxypropyl)etiocholan-3a-ol
Lithocholate
LITHOCHOLIC ACID //BP
Lithocholic acid,3α-Hydroxy-5β-cholan-24-oic acid, 3α-Hydroxy-5β-cholanic acid, 5β-Cholan-24-oic acid-3α-ol
HYDROYCHOLANIC ACID
3β-Hydroxyallocholanic acid
Lithocholic aCld
Lithocholic Acide
3-alpha-hydroxy-5-beta-cholanicaci
5BETA-CHOLAN-24-OIC ACID-3A-OL
3-alpha-hydroxy-5-beta-cholan-24-oicaci
(3a,5b)-3-hydroxycholan-24-oic acid
5BETA-CHOLANIC ACID-3ALPHA-OL
5beta-Cholan-24-oic acid, 3alpha-hydroxy
3ALPHA-HYDROXY-5BETA-CHOLAN-24-OIC ACID
3α-Hydroxy-5β-cholan-24-oic acid
3ALPHA-HYDROXY-5BETA-CHOLANIC ACID
(R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
Cholan-24-oic acid, 3-hydroxy-, (3α,5β)
5BETA-CHOLAN-24-OIC ACID-3ALPHA-OL
3α-Hydroxy-5β-cholan-24-oic acid, 3α-Hydroxy-5β-cholanic acid, 5β-Cholan-24-oic acid-3α-ol
3-HYDROXYCHOLANIC ACID
LITHOCHOLIC ACID
4-10-00-00785 (Beilstein Handbook Reference)
Ursodeoxycholic Acid Impurity C
5β-Cholanic Acid-3α-ol
NCI-C03861
Lithocolic acid
Lithocholic acid3alpha-Hydroxycholanic acid
(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,]
(3a,5b)-3-hydroxy-cholan-24-oic acid
5β-Cholan-24-oic acid-3α-ol
LithocholicAcid>
(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
ALPHA-HYDROXY-5BETA-CHOLANIC ACID
3α-Hydroxy-5β-cholan-24-oate
3α-hydroxy-5β-cholan-24-oic acid
Description Lithocholic acid is a toxic secondary bile acid, causes intrahepatic cholestasis, has tumor-promoting activity.Target: OthersLithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. It has also been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ. It has been implicated in human and experimental animal carcinogenesis. Preliminary in vitro research suggests that LCA selectively kills neuroblastoma cells, while sparing normal neuronal cells and is cytotoxic to numerous other malignant cell types at physiologically relevant concentrations.
Related Catalog
Target

Human Endogenous Metabolite

References

[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.
Density 1.1±0.1 g/cm3
Boiling Point 511.0±23.0 °C at 760 mmHg
Melting Point 183-188 °C(lit.)
Molecular Formula C24H40O3
Molecular Weight 376.573
Flash Point 276.9±19.1 °C
Exact Mass 376.297760
PSA 57.53000
LogP 6.70
Vapour Pressure 0.0±3.0 mmHg at 25°C
Index of Refraction 1.528
Storage condition Refrigerator

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
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes F+
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS FZ2275000
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