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LITHOCHOLIC ACID

Product Name
LITHOCHOLIC ACID
CAS No.
434-13-9
Chemical Name
LITHOCHOLIC ACID
Synonyms
Lithocolic acid;NCI-C03861;Lithocholate;(R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid;NCI-CO-3861;lithocholicaci;LITHOCHOLIC ACID;Lithocholic aCld;Stone cholic acid;Lithocholic Acide
CBNumber
CB2342229
Molecular Formula
C24H40O3
Formula Weight
376.57
MOL File
434-13-9.mol
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LITHOCHOLIC ACID Property

Melting point:
183-188 °C (lit.)
alpha 
D20 +33.7° (c = 1.5 in abs ethanol); D19 +23.3° (Wieland); D20 +32.1° (Fischer)
Boiling point:
445.09°C (rough estimate)
Density 
1.0454 (rough estimate)
refractive index 
35.5 ° (C=1, EtOH)
Flash point:
9℃
storage temp. 
room temp
solubility 
Chloroform (Slightly), Dichloromethane (Slightly, Heated), DMSO (Slightly, Heated)
pka
4.76±0.10(Predicted)
form 
Powder
color 
White to off-white
optical activity
+3220 (c 1.5, ethanol)
Water Solubility 
18.83ug/L(25 ºC)
Merck 
5545
BRN 
3217757
InChIKey
SMEROWZSTRWXGI-HVATVPOCSA-N
LogP
6.700 (est)
CAS DataBase Reference
434-13-9(CAS DataBase Reference)
EPA Substance Registry System
Lithocholic acid (434-13-9)
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Safety

Safety Statements 
22-24/25
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
2
RTECS 
FZ2275000
HS Code 
29181998
Hazardous Substances Data
434-13-9(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H370Causes damage to organs

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
L6250
Product name
Lithocholic acid
Purity
≥95%
Packaging
10g
Price
$77
Updated
2024/03/01
Cayman Chemical
Product number
20253
Product name
Lithocholic Acid
Purity
≥95%
Packaging
5g
Price
$33
Updated
2024/03/01
Cayman Chemical
Product number
20253
Product name
Lithocholic Acid
Purity
≥95%
Packaging
10g
Price
$60
Updated
2024/03/01
Sigma-Aldrich
Product number
L6250
Product name
Lithocholic acid
Purity
≥95%
Packaging
25g
Price
$264
Updated
2024/03/01
Sigma-Aldrich
Product number
L0720800
Product name
Lithocholic acid
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
l0720800
Price
$220
Updated
2024/03/01
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LITHOCHOLIC ACID Chemical Properties,Usage,Production

Chemical Properties

white to off-white powder

Uses

LD50(mouse) 3900 mg/kg po

Uses

Cholagogue;Anticholelithogenic

Uses

Lithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. It has also been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ.

Uses

A cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

Definition

ChEBI: A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.

General Description

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

Air & Water Reactions

Insoluble in water.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition LITHOCHOLIC ACID emits acrid smoke and fumes.

Fire Hazard

Flash point data for LITHOCHOLIC ACID are not available. LITHOCHOLIC ACID is probably combustible.

Biological Activity

lithocholic acid (lca) is a toxic secondary bile acid, causing intrahepatic cholestasis, which has tumor-promoting activity.

in vitro

among 17 kinds of bile acids with respect to inhibition of mammalian dna polymerases, only lca and its derivatives inhibited dna polymerases, while other bile acids did not show inhibitory effect [1].

in vivo

administration of lca and its conjugates to rodents causes intrahepatic cholestasis, which is a pathogenic state characterized by decreased bile flow and the accumulation of bile constituents in the liver and blood [2].

Purification Methods

Lithocholic acid can be purified by conversion to the rather insoluble Na or K salt by addition of the equivalent amount of aqueous NaOH or KOH, filtering off the alkali salt, washing it with ice cold H2O, dissolving it in the least volume of boiling H2O, acidifying with the dilute HCl (slight excess), filtering off the acid, washing with cold H2O and drying it thoroughly in a vacuum. Recrystallise it from Me2CO, EtOH or acetic acid. The methyl ester crystallises from MeOH, with 0.5 mol of MeOH, and has m 92-93o, [] D 25 +34o (MeOH). It has also been purified by recrystallisation from pet ether (b 40-60o) and, after chromatography on Al2O3 in pet ether, gave a labile form m 92-93o which is transformed to the stable form m 125-126o after standing for 2days in a vacuum desiccator. [Hoelm & Mason J Am Chem Soc 62 569 1940, Sarel & Yanuka J Org Chem 24 2018 1959, Beilstein 10 IV 785.]

References

[1] ogawa a, murate t, suzuki m, nimura y, yoshida s. lithocholic acid, a putative tumor promoter, inhibits mammalian dna polymerase beta. jpn j cancer res. 1998 nov;89(11):1154-9.
[2] staudinger jl, goodwin b, jones sa, hawkins-brown d, mackenzie ki, latour a, liu y, klaassen cd, brown kk, reinhard j, willson tm, koller bh, kliewer sa. the nuclear receptor pxr is a lithocholic acid sensor that protects against liver toxicity. proc natl acad sci u s a. 2001 mar 13;98(6):3369-74.

LITHOCHOLIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from LITHOCHOLIC ACID manufacturers

HebeiShuoshengImportandExportco.,Ltd
Product
LITHOCHOLIC ACID 434-13-9
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-09
Hebei Longbang Technology Co., Ltd
Product
LITHOCHOLIC ACID 434-13-9
Price
US $5.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20TONS
Release date
2024-05-13
Hebei Jingbo New Material Technology Co., Ltd
Product
LITHOCHOLIC ACID 434-13-9
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000000
Release date
2024-01-05

434-13-9, LITHOCHOLIC ACIDRelated Search:

Ursodeoxycholic acid (4R)-4-[(3S,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 Allo-UDCA Cholic acid Deoxycholic acid 3-ALPHA-HYDROXY-6-KETOCHOLANIC ACID (+)-NEOMENTHOL (2R,5S)-5-(5-Fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,3-oxathiolane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester (2S)-2-[[[(1,1-Dimethylethyl)diphenylsilyl]oxy]methyl]-1,3-oxathiolan-5-ol 5-Acetate Emtricitabine Impurity 18 5-fluoro-1-(2-(hydroxymethyl)-1,3-dioxolan-4-yl)cytosine 5-epi EMtricitabine 2,4(1H,3H)-Pyrimidinedione,5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2S-cis)- (9CI) Emtricitabine Emtricitabine Impurity 8 ISOPULEGOL, TECH. 156198-94-6 EMTRICITABINE-13C,15N2

  • 17-beta-(1-Methyl-3-carboxypropyl)ethiocholan-3-alpha-ol
  • 17beta-(1-methyl-3-carboxypropyl)etiocholan-3alpha-ol
  • BETA-CHOLANIC ACID-3-ALPHA-OL
  • HYDROYCHOLANIC ACID
  • 3-HYDROXYCHOLANIC ACID
  • 3ALPHA-HYDROXYCHOLANIC ACID
  • 3ALPHA-HYDROXY-5BETA-CHOLANIC ACID
  • 3ALPHA-HYDROXY-5BETA-CHOLAN-24-OIC ACID
  • 5BETA-CHOLAN-24-OIC ACID-3A-OL
  • 5BETA-CHOLAN-24-OIC ACID-3ALPHA-OL
  • 5BETA-CHOLANIC ACID-3ALPHA-OL
  • LITHOCHOLIC ACID
  • Ursodeoxycholic Acid Impurity 3（Ursodeoxycholic Acid EP Impurity C）
  • Lithocolic acid
  • NCI-C03861
  • 3α-Hydroxy-5β-cholan-24-oic acid
  • 3α-Hydroxy-5β-cholanic acid
  • 5β-Cholan-24-oic acid-3α-ol
  • Lithocholic Acide
  • Lithocholic acid,3α-Hydroxy-5β-cholan-24-oic acid, 3α-Hydroxy-5β-cholanic acid, 5β-Cholan-24-oic acid-3α-ol
  • 17β-(1-Methyl-3-car-boxypropyl) etiocholan-3α-ol
  • (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,]
  • LITHOCHOLIC ACID(RG)
  • 3α-Hydroxy-5β-cholan-24-oic acid, 3α-Hydroxy-5β-cholanic acid, 5β-Cholan-24-oic acid-3α-ol
  • 3β-Hydroxyallocholanic acid
  • NCI-CO-3861
  • Lithocholic acid,98%
  • Lithocholic acid3alpha-Hydroxycholanic acid
  • Lithocholic acid, 98% 5GR
  • (3α,5β)-3-Hydroxycholan-24-oic Acid
  • 3α-Hydroxy-5β-cholan-24-oate
  • 3α-Hydroxy-5β-cholanoic Acid
  • 5beta-Cholanic Acid-3alpha-ol 3alpha-Hydroxy-5beta-cholanic Acid
  • 3-alpha-hydroxy-5-beta-cholan-24-oicaci
  • 3alpha-hydroxy-5beta-cholan-24-oicaci
  • 3-alpha-hydroxy-5-beta-cholanicaci
  • 3alpha-Hydroxy-5beta-cholanoic acid
  • 3alpha-hydroxy-5beta-cholanoicacid
  • 3-hydroxy-,(3-alpha,5-beta)-cholan-24-oicaci
  • 3-hydroxy-,(3alpha,5beta)-cholan-24-oicaci
  • 3-Hydroxycholan-24-oic acid
  • 3-hydroxycholan-24-oicacid
  • 5beta-Cholan-24-oic acid, 3alpha-hydroxy-
  • 5-beta-Cholanic acid, 3-alpha-hydroxy-
  • Cholan-24-oic acid, 3-hydroxy-, (3alpha,5beta)-
  • Lithocholate
  • Cholan-24-oic acid, 3-hydroxy-, (3α,5β)-
  • Lithocholic aCld
  • LITHOCHOLIC ACID >=95%
  • Ursodeoxycholic Acid EP Impurity C
  • Stone cholic acid
  • (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
  • Chenodeoxycholic Acid Impurity 3
  • Lithocholic acid CRS
  • LithocholicAcid&gt
  • LITHOCHOLIC ACID USP/EP/BP
  • Chenodeoxycholic acid EP Impurity C
  • ALPHA-HYDROXY-5BETA-CHOLANIC ACID