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83-44-3

83-44-3 structure
83-44-3 structure
  • Name: Deoxycholic acid
  • Chemical Name: Deoxycholic Acid
  • CAS Number: 83-44-3
  • Molecular Formula: C24H40O4
  • Molecular Weight: 392.572
  • Catalog: Biochemical Chinese herbal medicine ingredients
  • Create Date: 2018-03-19 08:00:00
  • Modify Date: 2026-07-01 21:22:36
  • 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
Synonyms Cholan-24-oicacid,3,12-dihydroxy-,(3.alpha.,5.beta.,12.alpha.)
5β-Deoxycholic Acid
DEOXYCHOLIC ACID
desoxycholsaeure
DESOXYCHOLIC ACID
cholorebic
3,12-dihydroxy-,(3-alpha,5-beta,12-alpha)-cholan-24-oicaci
7alpha-deoxycholicacid
EINECS 201-478-5
3alpha,12alpha-dihydroxy-5beta-cholan-24-oicaci
12α -Dihydroxy-5β-cholan-24-oic acid
7α-Deoxycholic acid
Deoxy-cholic Αcid
ATX-101
3ALPHA,12ALPHA-DIHYDROXY-5BETA-CHOLAN-24-OIC ACID
3ALPHA,12ALPHA-DIHYDROXYCHLOLANIC ACID
Dihydroxycholanoic acid
stochol
3-ALPHA,12-ALPHA-DIHYDROXYCHOLANIC ACID
pyrochol
5B-CHOLAN-24-OIC ACID-3A,12A-DIOL
3,12-dihydroxycholanicacid
(R)-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-diMethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
17b-(1-Methyl-3-carboxypropyl)etiocholane-3a,12a-diol
deoxy-Cholic acid
3α,12α-dihydroxy-5β-cholan-24-oic acid
(3alpha,5beta,12alpha)-3,12-dihydroxy-cholan-24-oic acid
17B-(1-METHYL-3-CBOXYPROPYL)ETIOCHOLANE-3A,12A-DIOL
DEOXYCHOLIC ACID FREE ACID
Stocholl
3α,12α-Dihydroxy-5β-dhoianic acid
(3a,5b,12a)-3,12-Dihydroxy-5-cholan-24-oic Acid
Deoxycholic acid, R
5-BETA-CHOLANIC ACID-3-ALPHA, 12-ALPHA-DIOL
3alpha,12alpha-dihydroxy-5beta-cholanoicacid
deoxycholic
3,12-dihydroxy-,(3alpha,5beta,12alpha)-cholan-24-oicaci
3-alpha,12-alpha-dihydroxy-5-beta-cholan-24-oicaci
3-alpha,12-alpha-dihydroxy-5-beta-cholanoicacid
deoxcholic acid
3,12-dihydroxy-,(3.alpha.,5.beta.,12.alpha.)-Cholan-24-oicacid
(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
5-beta-deoxycholicacid
cholerebic
5β-Cholan-24-oic acid-3α,12α-diol
3ALPHA, 12ALPHA-DIHYDROXY-5BETA-CHOLANIC ACID
(4R)-4-[(3R,5R,8R,9S,10S,12S,13S,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]pentanoate
7-DEOXYCHOLIC ACID
17β-(1-Methyl-3-cboxypropyl)etiocholane-3α,12α-diol
5β-Cholanic Acid-3α,12α-diol
deoxycholaticacid
5BETA-CHOLAN-24-OIC ACID-3ALPHA,12ALPHA-DIOL
5b-Deoxycholic acid
l7-beta-(1-methyl-3-cboxypropyl)-etiocholane-3-alpha,12-alpha-diol
5BETA-CHOLAN-3ALPHA, 12BETA-DIOL
3,12-dihydroxy-(3alpha,5beta,12alpha)-cholan-24-oi
Deoxycholatic acid
DEOXYCHOLIC ACID FREE ACID SIGMAULTRA
degalol
CHOLAIC ACID
(3α,5β,12α)-3,12-Dihydroxycholan-24-oic acid
Kybella
droxolan
5b-Cholanic acid-3a,12a-diol
3α,12α-Dihydroxy-5β-cholanoic Acid
CHOLEIC ACID
17-beta-(1-methyl-3-cboxypropyl)-etiocholane-3-alpha,12-alpha-diol
Chenodeoxycolic acid(Chenodiol)95
3-alpha,12-alpha-dihydroxycholansaeure
deoxy-cholicaci
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
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)

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
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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