Deoxycholic Acid

• Catalog Number: ACM83443-1
• Product Name: Deoxycholic Acid
• CAS: 83-44-3
• Category: Heterocyclic Organic Compound
• 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
• Molecular Weight: 392.58
• Molecular Formula: C24H40O4
• 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.