Deoxycholic acid

Modify Date: 2024-01-02 16:21:32

Deoxycholic acid structure	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	Chinese USA	Flash Point	298.8±22.4 °C
	Symbol	GHS07	Signal Word	Warning

Use of Deoxycholic acid

Deoxycholic acid is specifically responsible for activating the G protein-coupled bile acid receptor TGR5 that stimulates brown adipose tissue (BAT) thermogenic activity.

Name	Deoxycholic Acid
Synonym	More Synonyms

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 >> GPCR19 Natural Products >> Steroids Research 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.

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
Water Solubility	0.24 g/L (15 ºC)

Deoxycholic acid MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ2100000

CHEMICAL NAME :: 5-beta-Cholan-24-oic acid, 3-alpha,12-alpha-dihydroxy-

CAS REGISTRY NUMBER :: 83-44-3

BEILSTEIN REFERENCE NO. :: 3219882

LAST UPDATED :: 199701

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C24-H40-O4

MOLECULAR WEIGHT :: 392.64

WISWESSER LINE NOTATION :: L E5 B666TJ A1 DQ E1 FY1&2VQ OQ

HEALTH HAZARD DATA

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)

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

Precursor 9
CAS#:3245-38-3 Cholan-24-oic a... CAS#:28050-47-7 Methyl 3α-hydro... CAS#:27240-83-1 5BETA-CHOLANIC ... CAS#:434-13-9 Lithocholic acid
CAS#:4472-02-0 5.beta.-Chol-9 ... CAS#:560-62-3 9-Hydroxyandros... CAS#:1093397-61-5 9alpha-hydroxy-... CAS#:1093397-63-7 5β-androst-9(11...
CAS#:571-49-3 9(11), (5-BETA)...
DownStream 8
CAS#:360-65-6 GLYCODEOXYCHOLI... CAS#:3245-38-3 Cholan-24-oic a... CAS#:15173-30-5 5b-Cholan-24-oi... CAS#:434-13-9 Lithocholic acid
CAS#:513-49-5 (S)-(+)-2-Amino... CAS#:2287-93-6 Cholan-24-oic a... CAS#:2387-23-7 1,3-Dicyclohexylurea CAS#:516-50-7 taurodeoxycholi...

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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

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China
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