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Merck

L6250

Lithocholic acid

≥95%

Synonym(s):

3α-Hydroxy-5β-cholan-24-oic acid, 3α-Hydroxy-5β-cholanic acid, 5β-Cholan-24-oic acid-3α-ol

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10 G

₪487.00

25 G

₪1,427.00

₪487.00


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About This Item

Empirical Formula (Hill Notation):
C24H40O3
CAS Number:
Molecular Weight:
376.57
UNSPSC Code:
12352106
NACRES:
NA.25
PubChem Substance ID:
EC Number:
207-099-1
Beilstein/REAXYS Number:
3217757
MDL number:

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Product Name

Lithocholic acid, ≥95%

InChI key

SMEROWZSTRWXGI-HVATVPOCSA-N

InChI

1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1

SMILES string

[H][C@]12CC[C@@]3([H])[C@]4([H])CC[C@H]([C@H](C)CCC(O)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2

biological source

bovine bile

assay

≥95%

mol wt

376.57 g/mol

mp

183-188 °C (lit.)

functional group

carboxylic acid

shipped in

ambient

storage temp.

room temp

Quality Level

Gene Information

human ... POLA1(5422), TOP2A(7153)
rat ... Polb(29240)

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Show Differences

1 of 4

This Item
L0720800BP927700218P
assay

≥95%

assay

-

assay

-

assay

99% (TLC)

storage temp.

room temp

storage temp.

-

storage temp.

2-8°C

storage temp.

−20°C

mol wt

376.57 g/mol

mol wt

-

mol wt

-

mol wt

-

biological source

bovine bile, synthetic

biological source

-

biological source

-

biological source

-

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

mp

183-188 °C (lit.)

mp

183-188 °C (lit.)

mp

183-188 °C (lit.)

mp

-

Application

Lithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. [1] It has also been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ. [2]

Biochem/physiol Actions

Bile Acid

General description

Lithocholic acid is an oligo(ethylene glycol) derivative of bile acid. [3]

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Katarzyna Magiera et al.
Cell chemical biology, 24(4), 458-470 (2017-03-28)
USP2a is a deubiquitinase responsible for stabilization of cyclin D1, a crucial regulator of cell-cycle progression and a proto-oncoprotein overexpressed in numerous cancer types. Here we report that lithocholic acid (LCA) derivatives are inhibitors of USP proteins, including USP2a. The
Vincent R Richard et al.
Aging, 5(4), 234-269 (2013-04-05)
Macromitophagy controls mitochondrial quality and quantity. It involves the sequestration of dysfunctional or excessive mitochondria within double-membrane autophagosomes, which then fuse with the vacuole/lysosome to deliver these mitochondria for degradation. To investigate a physiological role of macromitophagy in yeast, we
Claudiu Saracut et al.
Acta cirurgica brasileira, 30(9), 624-631 (2015-10-16)
To assess whether deoxycholic acid (DOC) and lithocholic acid (LCA) administered in a period of six months in a concentration of 0.25% may have a carcinogenic role in mice colon. The study used C57BL6 female mice divided into four groups.
Satu Strandman et al.
The journal of physical chemistry. B, 117(1), 252-258 (2012-12-12)
Thermoresponsive characteristics of oligo(ethylene glycol) derivatives of lithocholic acid (LCA) depend on the hydrophilic/hydrophobic balance of the compounds. Below a threshold temperature (∼30 °C), one of the derivatives, LCA(EG(4))(2), self-assembles in water into hollow nanotubes that form thixotropic gels at
J Jehle et al.
British journal of pharmacology, 167(7), 1563-1572 (2012-08-01)
Heart failure and atrial fibrillation are associated with apoptosis of cardiomyocytes, suggesting common abnormalities in pro-apoptotic cardiac molecules. Activation of the receptor tyrosine kinase EphA2 causes apoptosis in vitro, and dysregulation of EphA2-dependent signalling is implicated in LEOPARD and Noonan

Protocols

Investigate bile acid roles in gut hormone profiles and glycemic control, vital for clinical labs exploring potential mechanisms.

Related Content

Bile Acids (BA) are synthesized in the liver and play important roles in cholesterol homeostasis, absorption of vitamins and lipids, and various key metabolic processes.

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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