Chenodeoxycholic acid

Structural formula
General
Non-proprietary name	Chenodeoxycholic acid
other names	3 α , 7 α -dihydroxycholanoic acid; (4 R ) -4 - [(3 R , 5 S , 7 R , 8 R , 9 S , 10 S , 13 R , 14 S , 17 R ) -3,7-dihydroxy-10,13-dimethyl-2 , 3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1 H -cyclopenta [ a ] phenanthren-17-yl] pentanoic acid ( IUPAC ) ; Chenodiol;
Molecular formula	C 24 H 40 O 4
Brief description	white crystalline powder
External identifiers / databases
EC number	207-481-8
ECHA InfoCard	100.006.803
PubChem	10133
ChemSpider	9728
DrugBank	DB06777
Wikidata	Q419028
Drug information
ATC code	A05 AA01
properties
Molar mass	392.57 g mol −1
Physical state	firmly
Melting point	165-167 ° C
solubility	practically insoluble in water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319
	P: 305 + 351 + 338
Toxicological data	4000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Along with cholic acid, chenodeoxycholic acid is one of the primary bile acids . Chemically it is a steroid belonging to the group of sterols (sterols) . Their salts are called chenodeoxycholates .

It was first isolated from the gall of geese (old Greek: χήν = goose).

biochemistry

education

Chenodeoxycholic acid is one of the four most common acids produced by the liver . There it is formed from cholesterol via the intermediate stage pregnenolone .

function

Chenodeoxycholic acid and the other gall acids act as emulsifiers . During digestion they emulsify fats and make them accessible to the lipases .

About 90% of the gall acids are absorbed in the small intestine and thus get back into the liver for reuse.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on chenodeoxycholic acid in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
^ Carey MC (December 1975): Editorial: Cheno and urso: what the goose and the bear have in common . N. Engl. J. Med. 293 (24): 1255-1257. doi: 10.1056 / NEJM197512112932412 .
^ Voet & Voet, Biochemistry (second edition), pp. 694-704, publisher: Wiley & Sons.

literature

J. Greenberger, G. Paumgartner; C. Büning and H. Schmidt: Diseases of the biliary tract and gall bladder. Harrison's Internal Medicine, 16th Edition. ABW Wissenschaftsverlag, 2005 (PDF file; 332 kB)

Web links

Wikibooks: Biosynthesis of Bile Acids - Learning and Teaching Materials

Entries in the NIH study register

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f Entry on chenodeoxycholic acid in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[2] Carey MC (December 1975): Editorial: Cheno and urso: what the goose and the bear have in common . N. Engl. J. Med. 293 (24): 1255-1257. doi: 10.1056 / NEJM197512112932412 .

[3] Voet & Voet, Biochemistry (second edition), pp. 694-704, publisher: Wiley & Sons.