Deoxycholic Acid

• CAS: 83-44-3
• Catalog Number: ACM83443-1
• Category: Other Products
• Molecular Weight: 392.58
• Molecular Formula: C24H40O4
• Description: Deoxycholic acid (DCA) is a bile acid that plays an important role in the digestion and absorption of dietary fats and fat-soluble vitamins.
• Synonyms: Choleic acid
• IUPAC Name: (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-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
• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
• InChI: InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
• InChI Key: KXGVEGMKQFWNSR-LLQZFEROSA-N
• Boiling Point: 547.1±35.0 °C at 760 mmHg
• Melting Point: 171-174 °C(lit.)
• Flash Point: 298.8±22.4 °C
• Density: 1.1±0.1 g/mL
• Solubility: Soluble in water (0.24 g/l).
• Appearance: White to off-white solid
• Application: It is a natural component of the human body and is produced in the liver from cholesterol. It is also used in laboratory experiments to study the effects of bile acids on cell physiology, metabolism, and gene expression.
• Storage: Room temperature
• Complexity: 605
• Covalently-Bonded Unit Count: 1
• EC Number: 201-478-5
• Exact Mass: 392.292664
• Formal Charge: 0
• Hazard Codes: Xn:Harmful
• Hazard Statements: H302
• Heavy Atom Count: 28
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 3
• IC50 Target: G-protein coupled bile acid receptor 1: EC5050 = 1.25 µM (human)
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• MDL Number: MFCD00003673
• Monoisotopic Mass: 392.29265975 g/mol
• Optical Activity: α20D 56, c = 1 in EtOH
• Physical State: Solid
• pKa: pKa: 4.76
• PSA: 77.76
• Refractive Index: 1.543
• Rotatable Bond Count: 4
• Shipping: Ambient temperature
• Supplemental Hazard Statements: H225-H301+H311+H331-H370-H302-H315-H319-H335
• Symbol: GHS02,GHS06,GHS08,GHS07
• Topological Polar Surface Area: 77.8 Å2
• Vapor Pressure: 0.0±3.3 mmHg at 25°C
• WGK Germany: 3
• XLogP3: 4.66
• XLogP3-AA: 4.9

Case Study

Preparation of a novel deoxycholic acid-O-carboxymethylated chitosan-folic acid conjugates

Wang F, et al. Carbohydrate polymers, 2011, 84(3): 1192-1200.

A novel conjugate was prepared using deoxycholic acid (DOCA), O-carboxymethylated chitosan (OCMC) and folic acid (FA), which can be used in cancer-targeted drug delivery systems.
Synthesis of Conjugates
· Modification of OCMC with DOCA: OCMC was hydrophobically modified with DOCA to obtain a new amphiphilic polymer. To activate the carboxylic acid groups of DOCA in dried DMSO, equal amounts of EDC and NHS were added into the solution, which allowing the formation of an amide linkage by the reaction with primary amino groups in OCMC.
· Synthesis of DOMC-FA conjugates: Folate was attached to the surface amino groups of DOMC via a carbodiimide reaction.

Custom Q&A

What is the molecular formula of deoxycholic acid?

The molecular formula of deoxycholic acid is C24H40O4.

What is the molecular weight of deoxycholic acid?

The molecular weight of deoxycholic acid is 392.6 g/mol.

How is deoxycholic acid described in terms of its chemical structure?

Deoxycholic acid is described as a bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.

What role does deoxycholic acid play as a human blood serum metabolite?

Deoxycholic acid serves as a human blood serum metabolite.

What is the IUPAC name of deoxycholic acid?

The IUPAC name of deoxycholic acid is (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-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.

How does deoxycholic acid function when injected subcutaneously?

When injected subcutaneously, deoxycholic acid disrupts cell membranes in adipocytes and destroys fat cells in that tissue.

When was deoxycholic acid approved by the FDA for the treatment of submental fat?

Deoxycholic acid was approved by the FDA for the treatment of submental fat in April 2015.

What brand name is deoxycholic acid marketed under for submental fat reduction?

Deoxycholic acid is marketed under the brand name Kybella by Kythera Biopharma.

What is the chemical structure of deoxycholic acid represented in its Canonical SMILES?

The Canonical SMILES representation of deoxycholic acid is CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C.

As a naturally occurring bile acid, what specific type of fat does deoxycholic acid demonstrate a relative selectivity for?

Deoxycholic acid demonstrates a relative selectivity for fat over other tissues as a naturally occurring bile acid.