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CAS No.: | 81-23-2 |
---|---|
Name: | Dehydrocholic acid |
Article Data: | 35 |
Molecular Structure: | |
Formula: | C24H34O5 |
Molecular Weight: | 402.531 |
Synonyms: | 5b-Cholan-24-oic acid,3,7,12-trioxo- (8CI);3,7,12-Tri-keto-5b-Cholan-24-oic acid;3,7,12-Triketo-5b-cholanic acid;3,7,12-Triketocholanic acid;3,7,12-Trioxo-5b-cholan-24-oic acid;3,7,12-Trioxo-5b-cholanic acid;3,7,12-Trioxocholanic acid;Acolen;Bilidren;Bilostat;Cholagon;Cholan DH;Cholepatin;Cholic acid, dehydro-;Cholimed;Chologon;DHC;Decholin;Dehychol;Dehycon; |
EINECS: | 201-335-7 |
Density: | 1.172 g/cm3 |
Melting Point: | 238-240 °C |
Boiling Point: | 581.5 °C at 760 mmHg |
Flash Point: | 319.5 °C |
Solubility: | 10 mg/mL in ethanol |
Appearance: | white to off-white amorphous powder |
Safety: | 24/25 |
PSA: | 88.51000 |
LogP: | 4.07330 |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium perchlorate; sodium chloride In water at 25℃; for 40h; pH=12; Electrochemical reaction; 50 mA; | 100% |
With sodium bromate; ammonium cerium (IV) nitrate In water; acetonitrile at 80℃; for 3h; Temperature; Green chemistry; | 95% |
With sodium bromate; ammonium cerium (IV) nitrate In water; acetonitrile at 80℃; for 3.3h; | 95% |
dehydrocholic acid
Conditions | Yield |
---|---|
With jones' reagent In acetone for 0.0833333h; | 100% |
dehydrocholic acid
Conditions | Yield |
---|---|
Stage #1: C27H46O5 With potassium sulfate; cerous nitrate at 8℃; for 2.33333h; Large scale; Stage #2: With Tetradecanoic acid 1-methylethyl ester for 3h; Temperature; Large scale; | 94% |
cholic acid
A
3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid
B
7-ketodeoxycholic acid
C
7,12-dioxolitocholic acid
D
dehydrocholic acid
Conditions | Yield |
---|---|
With sodium hydroxide; sodium perchlorate; sodium chloride In water at 25℃; for 6h; pH=12; Product distribution; Further Variations:; electricity; Electrochemical reaction; 200 mA; | A 10% B 33% C 46% D 11% |
(24RS,25RS)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate
dehydrocholic acid
Conditions | Yield |
---|---|
With chromium(VI) oxide In water; acetic acid at 25℃; for 5h; | 90 mg |
Conditions | Yield |
---|---|
With Pseudomonas fluorescens B26 broth In water at 30℃; for 48h; | 41 % Chromat. |
IUPAC Name: (4R)-4-[(5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic Acid
Formula: C24H34O5
Molecular weight: 402.52 g/mol
The Molecular Structure of Dehydrocholic acid (CAS NO.81-23-2):
Density: 1.172 g/cm3
Melting Point: 238-240 °C
Flash Point: 319.5 °C
Boiling Point: 581.5 °C at 760 mmHg
Index of Refraction: 1.534
Molar Refractivity: 106.86 cm3
Molar Volume: 343.3 cm3
Surface Tension: 45.4 dyne/cm
Enthalpy of Vaporization: 95 kJ/mol
Vapour Pressure: 4.96E-15 mmHg at 25 °C
Solubility Ethanol: 10 mg/mL
Appearance: white to off-white amorphous powder
XLogP3-AA: 2.6
H-Bond Donor: 1
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Tautomer Count: 18
Exact Mass: 402.240624
MonoIsotopic Mass: 402.240624
Topological Polar Surface Area: 88.5
Heavy Atom Count: 29
Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(=O)CC3C2C(=O)CC4C3(CCC(=O)C4)C)C
InChI: InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
InChIKey: OHXPGWPVLFPUSM-KLRNGDHRSA-N
EINECS: 201-335-7
Product Categories: Bile Acids;Biochemistry;Steroids
Dehydrocholic acid (CAS NO.81-23-2) can be used as a gallbladder drug and very useful for the gallbladder and biliary tract dysfunction, post-cholecystectomy syndrome, chronic cholecystitis and cholelithiasis and chronic hepatitis.
Dehydrocholic acid is manufactured by the oxidation of cholic acid.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 1492mg/kg (1492mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Japanese Journal of Pharmacology. Vol. 22, Pg. 235, 1972. |
mouse | LD50 | oral | 3100mg/kg (3100mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 857, 1962. | |
mouse | LD50 | subcutaneous | 1620mg/kg (1620mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 116, Pg. 154, 1958. | |
rat | LD50 | intramuscular | 1500mg/kg (1500mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 244, 1954. | |
rat | LD50 | intravenous | 750mg/kg (750mg/kg) | Drugs in Japan Vol. 6, Pg. 495, 1982. | |
rat | LD50 | oral | 4gm/kg (4000mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 116, Pg. 154, 1958. |
Reported in EPA TSCA inventory.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: FZ2300000
Moderately toxic by ingestion, intravenous, intramuscular, and subcutaneous routes. When heated to decomposition it emits acrid smoke and fumes.
The chemical synonyms of Dehydrocholic acid (CAS NO.81-23-2) are 3,7,12-Triketo-5beta-cholanoic acid ; 3,7,12-Triketocholanic acid ; 3,7,12-Trioxo-5-beta-cholan-24-oic acid ; 3,7,12-Trioxo-5beta-cholan-24-oic acid ; 3,7,12-Trioxo-5beta-cholanic acid ; 3,7,12-Trioxocholanic acid ; 4-10-00-03478 (Beilstein Handbook Reference) ; 5beta-Cholanic acid, 3,7,12-trioxo- ; Acide dehydrocholique ; Acide dehydrocholique [French] ; Acide dehydrocholique [INN-French] ; Acido dehidrocolico ; Acido dehidrocolico [INN-Spanish] ; Acido dehidrocolico [Spanish] ; Acido deidrocolico ; Acido deidrocolico [DCIT] ; Acidum dehydrocholicum ; Acidum dehydrocholicum [INN-Latin] ; Chologon ; DHC ; Decholin ; Dee-Co ; Dehychol ; Erebile ; Felacrinos ; Hykolex ; Ketochol ; Ketocholanic acid ; Khologon ; NSC 8796 ; Novocolin ; Oxycholin ; Procholon ; Sanocholen ; Triketocholanic acid ; UNII-NH5000009I . Dehydrocholic acid (CAS NO.81-23-2) is dissolved in sodium hydroxide, slightly soluble in chloroform, slightly soluble in ethanol, practically insoluble in water.