Taurocholic acid: Difference between revisions

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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Taurocholic_acid.png|200px|{{PAGENAME}}]] <!-- replace if not identical with the pagename -->
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| [[IUPAC nomenclature|Chemical name]]
| <small>2-{[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-<br>24-oxocholan-24-yl]amino}ethanesulfonic acid</small>
|-
| [[Chemical formula]]
| C<sub>26</sub>H<sub>45</sub>NO<sub>7</sub>S
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| [[Molecular mass]]
| 515.7058 g/mol
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| [[CAS registry number|CAS number]]
| [81-24-3]
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| [[Density]]
| x.xxx g/cm<sup>3</sup>
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| [[Melting point]]
| 125.0 °C
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| [[Boiling point]]
| xx.x °C
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| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small>
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'''Taurocholic acid''' is a prominent bile acid, instrumental in the process of fat emulsification. Recognized by several other names such as '''cholaic acid''', '''cholyltaurine''', and '''acidum cholatauricum''', it primarily exists as a sodium salt in mammalian bile. Structurally, it is a conjugate formed by the combination of [[cholic acid]] and [[taurine]]. Both medically and commercially, taurocholic acid finds varied applications and is primarily derived from cattle bile.
{{Short description|A bile acid involved in the digestion of fats}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477239679
| ImageFile = Taurocholic acid.svg
| ImageSize = 200px
| IUPACName = 2-[[(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-yl]amino]ethanesulfonic acid
| OtherNames = N-Choloyltaurine
| Section1 = {{Chembox Identifiers
  | CASNo_Ref = <ref>{{Cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/Taurocholic-acid |title=Taurocholic acid |website=PubChem |access-date=2023-10-01}}</ref>
  | CASNo = 81-24-3
  | PubChem = 439225
  | ChemSpiderID = 388211
  | UNII = 7LYO5VOR8H
  | ChEBI = 28832
  | ChEMBL = 1201630
  | SMILES = C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@@H]1[C@H]2[C@H]3[C@@H](CC[C@]3(C)[C@H]2[C@@H](O)C1)O
  | InChI = 1S/C26H45NO7S/c1-16(2)7-8-19(28)27-9-10-35(32,33)34)26(6)14-18(30)22-20(26)11-12-21-23(22)15-24(31)25(21,3)13-17(16)4-5-17/h16-18,20-24,28,30-31H,4-15H2,1-3H3,(H,27,28)(H,32,33,34)/t16-,17-,18-,20-,21-,22+,23-,24-,25-,26-/m0/s1
  | InChIKey = RUDATBOHQWOJDD-CEGNMAFCSA-N
}}
| Section2 = {{Chembox Properties
  | C = 26
  | H = 45
  | N = 1
  | O = 7
  | S = 1
  | MolarMass = 515.7 g/mol
}}
}}


=== Overview ===
'''Taurocholic acid''' is a [[bile acid]] that is conjugated with [[taurine]]. It is one of the primary bile acids produced in the [[liver]] and is involved in the [[digestion]] and [[absorption]] of [[fats]] and [[fat-soluble vitamins]] in the [[small intestine]].
As a yellowish crystalline substance that is deliquescent, taurocholic acid plays an indispensable role in the digestive system. Its primary function involves assisting in the emulsification of fats, a critical step in digestion that facilitates the absorption of dietary lipids.


=== Medical Significance ===
==Biological Role==
In the field of medicine, taurocholic acid is revered for its cholagogue and cholerectic properties. These attributes make it useful for:
Taurocholic acid is synthesized in the liver from [[cholesterol]] and is secreted into the [[bile duct]]. It plays a crucial role in the emulsification of dietary fats, which is essential for their digestion by [[lipase]] enzymes. The presence of taurocholic acid in the intestine also facilitates the absorption of fat-soluble vitamins such as [[vitamin A]], [[vitamin D]], [[vitamin E]], and [[vitamin K]].
* Stimulating bile production in the liver.
* Enhancing bile secretion into the small intestine, which aids in the digestion and absorption of dietary fats.


=== Hydrolysis and Taurine ===
==Clinical Significance==
Upon undergoing hydrolysis, taurocholic acid yields [[taurine]], a nonessential amino acid that has several functions in the body. Taurine is pivotal for various physiological processes, including:
Abnormal levels of taurocholic acid can be indicative of liver dysfunction or [[bile acid malabsorption]]. It is also studied in the context of [[gallstone]] formation and [[cholestasis]].
* Regulating mineral balance in cells.
* Antioxidant activities.
* Modulating immune system health.
* Contributing to the proper function of the central nervous system.


=== Commercial Production ===
==See Also==
On a commercial scale, taurocholic acid is predominantly extracted from cattle bile, which is readily available as a byproduct of the meat-processing industry. This ensures efficient utilization of animal byproducts while also catering to medical and commercial needs.
 
=== See Also ===
* [[Cholic acid]]
* [[Cholic acid]]
* [[Taurine]]
* [[Glycocholic acid]]
* [[Bile acid]]
* [[Bile salt]]
* [[Lipid digestion]]


=== References ===
==References==
<references />
<references />
==See also==
 
* [[Deoxycholic acid]].
==External Links==
{{stub}}
* [https://pubchem.ncbi.nlm.nih.gov/compound/Taurocholic-acid PubChem - Taurocholic acid]
 
[[Category:Bile acids]]
[[Category:Bile acids]]
[[Category:Sulfonic acids]]
[[Category:Cholanes]]
[[Category:Cholanes]]
[[Category:Deliquescent substances]]
[[Category:Biochemistry]]

Revision as of 21:46, 29 December 2024


A bile acid involved in the digestion of fats


{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477239679 | ImageFile = Taurocholic acid.svg | ImageSize = 200px | IUPACName = 2-[[(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-yl]amino]ethanesulfonic acid | OtherNames = N-Choloyltaurine | Section1 = Template:Chembox Identifiers | Section2 = Template:Chembox Properties }}

Taurocholic acid is a bile acid that is conjugated with taurine. It is one of the primary bile acids produced in the liver and is involved in the digestion and absorption of fats and fat-soluble vitamins in the small intestine.

Biological Role

Taurocholic acid is synthesized in the liver from cholesterol and is secreted into the bile duct. It plays a crucial role in the emulsification of dietary fats, which is essential for their digestion by lipase enzymes. The presence of taurocholic acid in the intestine also facilitates the absorption of fat-soluble vitamins such as vitamin A, vitamin D, vitamin E, and vitamin K.

Clinical Significance

Abnormal levels of taurocholic acid can be indicative of liver dysfunction or bile acid malabsorption. It is also studied in the context of gallstone formation and cholestasis.

See Also

References

<references />

External Links

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