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81-25-4

81-25-4 structure
81-25-4 structure
  • Name: cholic acid
  • Chemical Name: cholic acid
  • CAS Number: 81-25-4
  • Molecular Formula: C24H40O5
  • Molecular Weight: 408.571
  • Catalog: API Digestive system medication Biliary medicine
  • Create Date: 2018-02-04 08:00:00
  • Modify Date: 2025-08-20 13:48:33
  • Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.
Name cholic acid
Synonyms Cholalic acid
Cholan-24-oic acid, 3,7,12-trihydroxy-, (3α,5β,7α,12α)- (9CI)
cholic acid
17b-(1-Methyl-3-carboxypropyl)etiocholane-3a,7a,12a-triol
3a,7a,12a-Trihydroxycholanic acid
5β-Cholic acid
3a,7a,12a-Trihydroxy-5b-cholanoic acid
(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
5b-Cholic acid
3a,7a,12a-Trihydroxy-5b-cholanic Acid
3α,7α,12α-trihydroxy-5β-cholan-24-oic acid
CHOLALIN
MFCD00003672
Cholan-24-oic acid, 3,7,12-trihydroxy-, (3α,5β,7α,8ξ,12α,20R)-
EINECS 201-337-8
Cholbam
Cholic&Cyclosphorine
3a,7a,12a-Trihydroxy-b-cholanic acid
3a,7a,12a-Trihydroxy-β-cholanic acid
Cholic acd
5b-Cholanic acid-3a,7a,12a-triol
AHR 3053-13C3
(3α,5β,7α,12α)-3,7,12-Trihydroxycholan-24-oic acid
3a,7a,12a-Trihydroxy-5b-cholan-24-oic Acid
5β-Cholanic acid, 3α,7α,12α-trihydroxy- (7CI)
CHOLATE
Kolbam
UNII-G1JO7801AE
Orphacol
Cholic acid, 5β-
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-oic acid
Cholan-24-oic acid, 3,7,12-trihydroxy-, (3α,5β,7α,12α)-
Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-α,5-β,7-α,12-α)-
(3α,5β,7α,8ξ,12α,20R)-3,7,12-Trihydroxycholan-24-oic acid
Description Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.
Related Catalog
Target

Human Endogenous Metabolite

In Vitro Cholic acid competitively binds Na+/taurocholate cotransporting polypeptide (NTCP) on HepG2 cells and significantly inhibits the uptake of Cholic acid (CA)-nanoliposomes (LPs)-Doxorubicin (DOX)-HCl, which indicates that CA-LPs-DOX-HCl are also uptaken via NTCP-mediated endocytosis pathway[1].
In Vivo Cholic acid feeding leads to increased CYP2D6 expression in CYP2D6-humanized mice. As a cholestasis model, Tg-CYP2D6 mice are fed a Cholic acid (CA)-supplemented diet for over 1 week. The treatment is known to increase bile acid pool size by 2-fold and to replace ~90% of bile acids with CA, recapitulating the features of cholestatic conditions in humans[2].
Cell Assay HepG2 cells are pretreated with the inhibitors NaN3 (1 mg/mL), Genistein (50 μg/mL), MβCD (10 mM), Nystatin (50 μg/mL), Chlorpromazine (10 μg/mL), and Cholic acid (1 mg/mL) for 30 min. After removing the inhibitors, the cells are incubated with CA-LPs for 2 h, and the cellular uptake of LPs is determined in the "In vitro cellular uptake assays" section[1].
Animal Admin Mice[2] Tg-CYP2D6 mice are fed with normal chow (control) or 1% (w/w) Cholic acid-supplemented diet (CA) for 14 days (n=4 mice/group). Alkaline phosphatase (ALP) and alanine aminotransferase (ALT) activities are measured in mouse serum.
References

[1]. Li Y, et al. Mechanism of hepatic targeting via oral administration of DSPE-PEG-Cholic acid-modified nanoliposomes. Int J Nanomedicine. 2017 Feb 28;12:1673-1684.

[2]. Pan X, et al. Cholic acid Feeding Leads to Increased CYP2D6 Expression in CYP2D6-Humanized Mice. Drug Metab Dispos. 2017 Apr;45(4):346-352.
Density 1.2±0.1 g/cm3
Boiling Point 583.9±50.0 °C at 760 mmHg
Melting Point 197-202 ºC
Molecular Formula C24H40O5
Molecular Weight 408.571
Flash Point 321.0±26.6 °C
Exact Mass 408.287567
PSA 97.99000
LogP 2.62
Vapour Pressure 0.0±3.7 mmHg at 25°C
Index of Refraction 1.558
Storage condition 2-8°C
Water Solubility 0.28 g/L (15 ºC)

CHEMICAL IDENTIFICATION

RTECS NUMBER :
FZ9350000
CHEMICAL NAME :
Cholic acid
CAS REGISTRY NUMBER :
81-25-4
BEILSTEIN REFERENCE NO. :
2822009
LAST UPDATED :
199701
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C24-H40-O5
MOLECULAR WEIGHT :
408.64
WISWESSER LINE NOTATION :
L E5 B666TJ A1 DQ E1 FY1&2VQ KQ OQ

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 :
4950 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
330 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TEST SYSTEM :
Rodent - rat
DOSE/DURATION :
7560 mg/kg/6W
REFERENCE :
CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 9,387,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84435 No. of Facilities: 174 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1744 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84435 No. of Facilities: 46 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 511 (estimated) No. of Female Employees: 325 (estimated)
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319
Precautionary Statements P305 + P351 + P338
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases S24/25
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS FZ9350000
HS Code 2942000000
HS Code 2942000000
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