Lithocholic Acid

less than 1 mg/mL at 67.5 °F (NTP, 1992)

FREELY SOL IN HOT ALC; MORE SOL IN BENZENE THAN DESOXYCHOLIC ACID; INSOL IN PETROLEUM ETHER, GASOLINE, WATER; SLIGHTLY SOL IN GLACIAL ACETIC ACID (ABOUT 0.2 G IN 3 ML); MORE SOL IN ETHER THAN CHOLIC OR DESOXYCHOLIC ACID; SOL IN ABOUT 10 TIMES ITS WT OF ETHYL ACETATE

In water, 0.38 mg/l at 25 °C.

0.000377 mg/mL

363 to 367 °F (NTP, 1992)

184-186 °C

186 °C

Hexagonal leaflets (from alcohols) or prisms (from acetic acid) or white powder. (NTP, 1992)

Solid

203.0 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6020779]

200.33 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

199.95 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

198.8 Ų [M+HCOO]- [CCS Type: DT; Method: single field calibrated]

203.1 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

210.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

CRYSTALS /ETHYL ESTER/

CRYSTALS /BENZYL ESTER/

CRYSTALS /ACETYLLITHOCHOLIC ACID/

FLAT NEEDLES FROM PENTANE /ACETYLLITHOCHOLIC ACID METHYL ESTER/

For more Other Experimental Properties (Complete) data for LITHOCHOLIC ACID (6 total), please visit the HSDB record page.

This chemical does not meet GHS hazard criteria for 42.9% (3 of 7) of reports.

Warning

H315 (57.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 7 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

SKIN TUMOR INHIBITION DECR IN FOLLOWING ORDER OF ACIDS: CHENODEOXYCHOLIC, LITHOCHOLIC, DEOXYCHOLIC, & CHOLIC.

16ALPHA-CYANOPREGNENOLONE (5 MG IP TWICE DAILY FOR 2 DAYS) INCR IN VITRO RAT LIVER MICROSOMAL 6BETA- & 7ALPHA-HYDROXYLATION OF LITHOCHOLIC ACID BY FACTORS OF 2 & 3-4 RESPECTIVELY. THIS MAY ACCOUNT FOR PREVENTION OF LITHOCHOLIC ACID-INDUCED CHOLELITHIASIS.

LITHOCHOLIC ACID (24)C(14) IS CONVERTED BY RAT LIVER HOMOGENATE INTO 3ALPHA-6BETA-DIHYDROXY-5BETA-CHOLANIC ACID. ADDN OF ETHANOL TO ENZYMATIC SYSTEM RESULTS IN INHIBITION OF FORMATION OF 3ALPHA, 6BETA-DIHYDROXY-5BETA-CHOLANIC ACID.

SODIUM LITHOCHOLATE INCR MNNG (N-METHYL-N'-NITRO-N-NITROSOGUANIDINE) INDUCED COLON TUMOR INCIDENCE IN BOTH GERM-FREE & CONVENTIONAL RATS (F344). /SODIUM LITHOCHOLATE/

LCA was also tested as a promoter of N-Nitrobis(2-hydroxypropyl)amine (BHP) induced carcinogenesis. Two groups of 5 to 6-wk-old hamsters (number not stated) were given 500 mg/kg BHP subcutaneously once per week for 5 weeks, and group 3 was given no further treatment; group 4 was given 0.5% LCA in feed for 30 weeks, all animals were autopsied at 35 weeks. There was no difference in food consumption or body weight between these 2 groups. There were no differences in number on liver lesions (group 3: 15/15 hyperplastic nodules, 2/15 hepatocellular carcinoma, 1/15 cholangiocarcinoma; group 4: 22/22 hyperplastic nodules, 3/22 hepatocellular carcinoma, 3/22 cholangiocarcinoma). However, there was a significant difference in the pancreatic tumors: group 3 had 4/15 gross tumors, 5/15 carcinomas, 4/15 adenomas while group 4 had 13/22 gross tumors, 15/22 carcinomas (P<.04) and 2/22 adenomas. Under the conditions of this experiment, LCA was not carcinogenic when administered alone, but was an effective promoter of BHP pancreatic carcinogenesis.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=434-13-9]

Lithocholic acid

TR-175: Bioassay of Lithocholic Acid for Possible Carcinogenicity (CASRN 434-13-9) (1979 )

08/31/78

No Evidence

No Evidence

No Evidence

PROLIFERATION OF ENDOPLASMIC RETICULUM WAS ONLY HEPATIC CHANGE OBSERVED IN RABBITS FOLLOWING 20 DAYS OF INGESTING FEED WITH LITHOCHOLIC ACID (50 MG/DAY). @ 30 DAYS CHANGES INCL PRESENCE OF INTRACYTOPLASMIC DENSE BODIES & ALTERATIONS OF HEPATOCELLULAR BILIARY POLE.

LITHOCHOLIC ACID (8 MG/DAY, BY GAVAGE), BETWEEN DAYS 1.5 & 2.5 LARGE DECR IN CHOLIC ACID CONCN & LITHOCHOLIC ACID & 3ALPHA,6BETA-DIHYDROXY-5BETA-CHOLANOIC ACID APPEARED IN INCR AMT, THESE CHANGES PRECEDED LIVER DAMAGE.

NO TUMORS WERE DETECTED IN RATS GIVEN INTRARECTAL DOSES OF SODIUM LITHOCHOLATE ALONE @ 20 MG/RAT 3 TIMES/WK FOR 48 WK. SODIUM LITHOCHOLATE INCR MNNG (N-METHYL-N'-NITRO-N-NITROSOGUANIDINE) INDUCED COLON TUMOR INCIDENCE IN BOTH GERM-FREE & CONVENTIONAL RATS (F344). /SODIUM LITHOCHOLATE/

THE EFFECTS OF LITHOCHOLIC ACID ON LIVER DRUG-METAB ENZYMES WAS MICROSOMAL EPOXIDE HYDRASE STIMULATION & GLUTATHIONE-S-TRANSFERASE INHIBITION.

For more Non-Human Toxicity Excerpts (Complete) data for LITHOCHOLIC ACID (7 total), please visit the HSDB record page.

A bioassay for the possible carcinogenicity of lithocholic acid was conducted using Fischer 344 rats and B6C3F1 mice. Lithocholic acid was admin by gavage, at either of two dosages, to groups of 50 male and 50 female animals of each species, except for 49 low dose female rats. Twenty animals of each sex and species were placed on test as controls. The high and low dosages of lithocholic acid admin were, respectively, 500 and 250 mg/kg for rats and 250 and 125 mg/kg for mice. The compound was admin to rats and mice for 103 wk. The period of cmpd admin was followed by an observation period of 1 wk for rats and 2 wk for mice. ... Adequate numbers of animals in all groups survived sufficiently long to be at risk from late-developing tumors. ... Under the conditions of this bioassay, lithocholic acid was not carcinogenic when administered by gavage to Fischer 344 rats or B6C3F1 mice. ... Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

LITHOCHOLIC ACID (24)C(14) IS CONVERTED BY RAT LIVER HOMOGENATE INTO 3ALPHA-6BETA-DIHYDROXY-5BETA-CHOLANIC ACID, 7SIGMA-HYDROXYLATION OCCURS, HYDROXYLATION CONJUGATION WITH TAURINE & FORMATION OF 3-SULFATE ESTER CAN BE DEMONSTRATED.

LABELED LITHOCHOLATE WAS INJECTED INTO GALLSTONE PATIENTS & HEALTHY VOLUNTEERS, MAJORITY OF RADIOACTIVITY IN BILE (50-60%) WAS PRESENT AS SULFATED CONJUGATES. DEGREE OF SULFATION WAS GREATER FOR GLYCINE THAN TAURINE CONJUGATES, WHICH SUGGESTED PREFERENTIAL SULFATION OF GLYCINE CONJUGATES.

Lithocholic Acid has known human metabolites that include 6alpha-Hydroxylithocholic acid.

Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

EXTRACTION FROM OX BILE (IN SALT FORM); FROM DEOXYCHOLIC ACID OR CHOLIC ACID

FROM CHOLIC OR DESOXYCHOLIC ACID.

...CHOLIC ACIDS REPRESENTED IN BILE...CHOLIC, DESOXYCHOLIC, & LITHOCHOLIC. ... FREE BILE ACIDS...COMBINE WITH FATTY ACIDS IN VARYING PROP...BY MEANS OF SECONDARY VALENCE FORCES TO FORM CHOLEIC ACIDS. LATTER ARE RESPONSIBLE FOR EMULSIFYING, DISPERSING, &...PROMOTING ABSORPTION OF FATS, CHOLESTEROL, & OIL-SOL VITAMINS.

FOUND IN OX BILE, HUMAN BILE, RABBIT BILE, & IN OX & PIG GALLSTONES.