cholic acid

Names

[ CAS No. ]:
81-25-4

[ Name ]:
cholic acid

[Synonym ]:
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

Biological Activity

[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]:

Natural Products >> Acids and Aldehydes

Research Areas >> Metabolic Disease

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ 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)

MSDS

Click to get detail MSDS

Toxicological Information

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)

Safety Information

[ Symbol ]:

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2942000000

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