30960

Deoxycholic acid

≥99.0% (T)

• Synonym(s): 3α,12α-Dihydroxy-5β-cholanic acid, 7-Deoxycholic acid, Desoxycholic acid
• Empirical Formula (Hill Notation): C₂₄H₄₀O₄
• CAS Number: 83-44-3
• Molecular Weight: 392.57
• Beilstein: 3219882
• EC Number: 201-478-5
• MDL number: MFCD00003673
• UNSPSC Code: 12352106
• PubChem Substance ID: 329753610
• NACRES: NA.77

Properties

• biological source: ox bile
• Quality Level: 100
• description: anionic
• Assay: ≥99.0% (T)
• form: powder
• optical activity: [α]20/D +54±1°, c = 1% in ethanol
• mol wt: 392.57 g/mol
• impurities: ≤1% cholic acid (TLC)
• mp: 170-175 °C; 171-174 °C (lit.)
• functional group: carboxylic acid
• SMILES string: C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
• 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
• Gene Information: human ... ATIC(471)

Description

General description

Deoxycholic acid is an amphiphilic molecule and an important constituent of bile acid. It contains hydroxyl groups substituted at the 3α and 12α positions and a carboxyl group towards the end of the branched-chain. These moieties contribute to the hydrophilic nature of the molecule and the hydrophobic cyclopentanophenanthrene forms its center.[1]

Application

Deoxycholic acid has been used as:

• a hyphal-inhibitory compound in an ex vivo assay to study the hyphal morphogenesis of Candida albicans in the gastrointestinal tract[2]
• an internal standard to estimate the toxin concentration in the cell pellet[3]
• a bile acid (BA) standard to quantitatively measure BA in various samples from treated mice by ultra-performance liquid chromatography triple quadrupole mass spectrometry[4]

Biochem/physiol Actions

Deoxycholic acid, due to its amphiphilicity, significantly helps to solubilize, emulsify, and absorb fat, vitamins, and cholesterol in the body.[1] High levels of intestinal deoxycholic acid might cause colorectal cancer by inducing oxidative stress and leading to DNA damage. It acts as an oncogene and pro-tumor factor.[5]

Other Notes

For the solubilization of the β-adrenergic receptor[6]

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H315,H319,H335
• Precautionary Statements: P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves