lithocholic acid
cholan-24-oic acid, 3-hydroxy-, (3-alpha,5-beta)- (9CI)
Identification
| Name | lithocholic acid |
| CAS Number | 434-13-9 |
| EINECS | 207-099-1 |
| FDA UNII | 5QU0I8393U |
| Molecular Formula | C24 H40 O3 |
| Molecular Weight | 376.58040000 |
| MDL Number | MFCD00003682 |
| Nikkaji Number | J1.532F |
| Beilstein | 3217757 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 186.00 °C. @ 760.00 mm Hg |
| Boiling Point | 511.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 530.00 °F. TCC ( 276.90 °C. ) (est) |
| logP (o/w) | 6.700 (est) |
| Soluble in | water, 0.377 mg/L @ 20 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-mouse LD50 3900 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for lithocholic acid usage levels up to | not for fragrance use. |
| Recommendation for lithocholic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
cholan-24-oic acid, 3-hydroxy-, (3-alpha,5-beta)- (9CI)
(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
3-alpha-
hydroxy-5-beta-cholanic acid
(3-alpha,5-beta)-3-
hydroxycholan-24-oic acid
17-beta-(1-
methyl-3-carboxypropyl)ethiocholan-3-alpha-ol
PubMed:
Consumption of vitamin B(6) reduces fecal ratio of lithocholic acid to deoxycholic acid, a risk factor for colon cancer, in rats fed a high-fat diet.
PubMed:
Consumption of some polyphenols reduces fecal deoxycholic acid and lithocholic acid, the secondary bile acids of risk factors of colon cancer.
PubMed:
Structural relationship of lithocholic acid derivatives binding to the N-terminal 8-kDa domain of DNA polymerase beta.
PubMed:
Three-dimensional structural model analysis of the binding site of lithocholic acid, an inhibitor of DNA polymerase beta and DNA topoisomerase II.
PubMed:
Possible anti-tumour-promoting activity of components in Japanese soybean fermented food, Natto: effect on gap junctional intercellular communication.
PubMed:
The role of the gallbladder in humans.
PubMed:
Burdock fermented by Aspergillus awamori elevates cecal Bifidobacterium, and reduces fecal deoxycholic acid and adipose tissue weight in rats fed a high-fat diet.
PubMed:
Metabolomics of ginger essential oil against alcoholic fatty liver in mice.
PubMed:
Synergistic induction of human cathelicidin antimicrobial peptide gene expression by vitamin D and stilbenoids.
PubMed:
Determination of bile acids by hollow fibre liquid-phase microextraction coupled with gas chromatography.
PubMed:
Influence of breast feeding, and adapted and hydrolyzed formulas on biliary bile acids in newborn guinea pigs.
PubMed:
[Modification of fecal bile acid excretion by fish oil in healthy probands].
PubMed:
Effect of taurine on total parenteral nutrition-associated cholestasis.
PubMed:
Small bowel resection and gastric acid hypersecretion.
PubMed:
Resolving self-assembly of bile acids at the molecular length scale.
PubMed:
In vitro transformation of cheno- and ursodeoxycholic acids and their 7-oleyl esters by human intestinal microflora.
PubMed:
Faecal pH, bile acid and sterol concentrations in premenopausal Indian and white vegetarians compared with white omnivores.
PubMed:
An international validation study of a Bhas 42 cell transformation assay for the prediction of chemical carcinogenicity.
PubMed:
Calcium supplementation modifies the relative amounts of bile acids in bile and affects key aspects of human colon physiology.
PubMed:
Dietary effects of barley fibre, wheat bran and rye bran on bile composition and gallstone formation in hamsters.
PubMed:
Effects of konjac glucomannan on putative risk factors for colon carcinogenesis in rats fed a high-fat diet.
PubMed:
Modulation of colonic xenobiotic metabolizing enzymes by feeding bile acids: comparative effects of cholic, deoxycholic, lithocholic and ursodeoxycholic acids.
PubMed:
Faecal steroid excretion in humans is affected by calcium supplementation and shows gender-specific differences.
PubMed:
Faecal weight, constituents, colonic motility, and lactose tolerance in the irritable bowel syndrome.
PubMed:
Effect of dried plums on colon cancer risk factors in rats.
PubMed:
Biochemical epidemiology of colon cancer: effect of types of dietary fiber on fecal mutagens, acid, and neutral sterols in healthy subjects.
PubMed:
Technical modification of the Balb/c 3T3 cell transformation assay: the use of serum-reduced medium to optimise the practicability of the protocol.
PubMed:
Effects of different types of dietary fiber preparations isolated from bamboo shoots, edible burdock, apple and corn on fecal steroid profiles of rats.
PubMed:
Cholelithiasis in hamsters: effects of cholic acid and calcium on gallstone formation.
PubMed:
Effects of a combined oestrogen-progestin preparation on gastric acid and pepsin secretion, serum gastrin concentration and biliary secretion of bile acids, phospholipids, and cholesterol in the cat.
PubMed:
Increasing ursodeoxycholic acid in the enterohepatic circulation of pigs through the administration of living bacteria.
PubMed:
Postprandial changes in serum unconjugated bile acid concentrations in healthy beagles.
PubMed:
Ursodiol: a cholesterol gallstone solubilizing agent.
PubMed:
Epimerization of the four 3,7-dihydroxy bile acid epimers by human fecal microorganisms in anaerobic mixed cultures and in feces.
PubMed:
Effect of cecum and appendix on 7 alpha-dehydroxylation and 7 beta-epimerization of chenodeoxycholic acid in the rabbit.
PubMed:
Age and diet effects on fecal bile acids in infants.
PubMed:
Determination of bile acids in human faecal samples using supercritical fluid extraction and high-performance liquid chromatography.
PubMed:
Serum unconjugated primary and secondary bile acids in patients with cholangiocarcinoma and hepatocellular carcinoma.
PubMed:
Simultaneous characterization of bile acid, sterols, and determination of acylglycerides in feces from soluble cellulose-fed hamsters using HPLC with evaporative light-scattering detection and APCI-MS.
PubMed:
Detection of initiating as well as promoting activity of chemicals by a novel cell transformation assay using v-Ha-ras-transfected BALB/c 3T3 cells (Bhas 42 cells).
PubMed:
Dietary fibre, physicochemical properties and their relationship to health.
PubMed:
Detection of tumor promoters by early antigen expression of EB virus in Raji cells using a fluorescence microplate-reader.
PubMed:
Transformation of sulfated bile acids by human intestinal microflora.