CAS 83-44-3|Deoxycholic acid
Introduction：Basic information about CAS 83-44-3|Deoxycholic acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Deoxycholic acid | ||
|---|---|---|---|
| CAS Number | 83-44-3 | Molecular Weight | 392.572 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 547.1±35.0 °C at 760 mmHg |
| Molecular Formula | C24H40O4 | Melting Point | 171-174 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 298.8±22.4 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | Deoxycholic Acid |
|---|---|
| Synonym | More Synonyms |
Deoxycholic acid BiologicalActivity
| Description | Deoxycholic acid is specifically responsible for activating the G protein-coupled bile acid receptor TGR5 that stimulates brown adipose tissue (BAT) thermogenic activity. |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>GPCR19Natural Products >>SteroidsResearch Areas >>Metabolic Disease |
| Target | Human Endogenous Metabolite |
| In Vitro | Deoxycholic acid (DCA) and chenoDeoxycholic acid (CDCA), as the common ingredients of duodenal reflux, act synergistically in many physiological and pathological processes. The cells are repeatedly exposed to 100 μM CDCA and Deoxycholic acid at pH 5.5 for up to 120 min. To simulate chronic local recurrent disease in vitro, the gastric cancer cell line MGC803 is exposed to acidified medium (pH 5.5) containing 100 μM Deoxycholic acid and CDCA. An untreated log-growth MGC803 cell line is generated to be used as a control in normal pH media. After daily 10 min exposure to the acidified bile acids for 60 weeks, MGC803-resistant cells are able to survive and proliferate after 120 min exposure[2]. |
| Cell Assay | MGC803 cells are cultured in Roswell Park Memorial Institute media supplemented with 10% fetal calf serum and 100 U/mL Penicillin and 100 mg/mL Streptomycin. To generate MGC803-resistant cells, the pH value of the MGC803 culture medium is adjusted to the experimental conditions using the hydrochloric acid (A). The bile acids GCDA and Deoxycholic acid are diluted to optimal working concentrations of 100 μM (B) with culture medium, and the overall pH (A+B) is adjusted to pH 5.5, simulating the gastric environment. Initially, MGC803 cells are chronically exposed to acidified medium with bile acids (A+B) for 10 min every 24 h. The experimental time and conditions are optimized in our preliminary experiments, which show that 10 min is enough and does not result in cell damage. This procedure is repeated and it takes 60 weeks for the MGC803 cells to survive and proliferate under the exposure of A+B for 120 min. Control untreated cells are cultured in neutral RPMI medium at pH 7.4 in parallel to the resistant cells for 60 weeks. The morphological changes in MGC803 cells exposed to acidified bile acids (A+B) are documented at 30 and 60 weeks[2]. |
| References | [1]. Somm E, et al. β-Klotho deficiency protects against obesity through a crosstalk between liver, microbiota, and brown adipose tissue. JCI Insight. 2017 Apr 20;2(8). pii: 91809. [2]. Wang X, et al. Acidified bile acids enhance tumor progression and telomerase activity of gastric cancer in micedependent on c-Myc expression. Cancer Med. 2017 Apr;6(4):788-797. |
Chemical & Physical Properties
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 547.1±35.0 °C at 760 mmHg |
| Melting Point | 171-174 °C(lit.) |
| Molecular Formula | C24H40O4 |
| Molecular Weight | 392.572 |
| Flash Point | 298.8±22.4 °C |
| Exact Mass | 392.292664 |
| PSA | 77.76000 |
| LogP | 4.66 |
| Vapour Pressure | 0.0±3.3 mmHg at 25°C |
| Index of Refraction | 1.543 |
| InChIKey | KXGVEGMKQFWNSR-LLQZFEROSA-N |
| SMILES | CC(CCC(=O)O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C |
| Water Solubility | 0.24 g/L (15 ºC) |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1 gm/kg
- TOXIC EFFECTS :
- Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 130 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 2 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2700 mg/kg/10W-I
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1120 mg/kg/22W-I
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application
- TYPE OF TEST :
- TD - Toxic dose (other than lowest)
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1400 mg/kg/22W-I
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 166 mg/kg
- SEX/DURATION :
- female 12-19 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
MUTATION DATA - TYPE OF TEST :
- Morphological transformation
- TEST SYSTEM :
- Rodent - hamster Embryo
- DOSE/DURATION :
- 7250 ug/L
- REFERENCE :
- TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 9,177,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80398 No. of Facilities: 153 (estimated) No. of Industries: 2 No. of Occupations: 7 No. of Employees: 3527 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80398 No. of Facilities: 82 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 2416 (estimated) No. of Female Employees: 1577 (estimated)
- TYPE OF TEST :
- Morphological transformation
- TEST SYSTEM :
- Rodent - hamster Embryo
- DOSE/DURATION :
- 7250 ug/L
- REFERENCE :
- TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 9,177,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80398 No. of Facilities: 153 (estimated) No. of Industries: 2 No. of Occupations: 7 No. of Employees: 3527 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80398 No. of Facilities: 82 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 2416 (estimated) No. of Female Employees: 1577 (estimated)
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302 |
| Precautionary Statements | P301 + P312 + P330 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn:Harmful |
| Risk Phrases | R22;R36/37/38 |
| Safety Phrases | S26-S36-S37/39 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | FZ2100000 |
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Synonyms
| 7-DEOXYCHOLIC ACID |
| Cholan-24-oic acid, 3,12-dihydroxy-, (3α,5β,12α)- |
| 5b-Deoxycholic acid |
| Deoxycholatic acid |
| EINECS 201-478-5 |
| Deoxycholic acid |
| 17b-(1-Methyl-3-carboxypropyl)etiocholane-3a,12a-diol |
| deoxy-Cholic acid |
| (3α,5β,12α)-3,12-Dihydroxycholan-24-oic acid |
| 7α-Deoxycholic acid |
| Kybella |
| 3α,12α-dihydroxy-5β-cholan-24-oic acid |
| ATX-101 |
| 5b-Cholanic acid-3a,12a-diol |
| Dihydroxycholanoic acid |
| Cholic acid, deoxy- |
| (3a,5b,12a)-3,12-Dihydroxy-5-cholan-24-oic Acid |
| (4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid |
| MFCD00003673 |
