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83-49-8

Basic Information
CAS No.: 83-49-8
Name: Hyodeoxycholic acid
Molecular Structure:
Molecular Structure of 83-49-8 (Hyodeoxycholic acid)
Formula: C24H40O4
Molecular Weight: 392.58
Synonyms: 3-alpha,6-alpha-Dihydroxy-5-beta-cholan-24-oic acid;3alpha,6alpha-Dihydroxy-5beta-cholan-24-saeure;3alpha,6alpha-Dihydroxycholanic acid;5-beta-Cholanic acid-3-alpha,6-alpha-diol;6-alpha-Hydroxylithocholic acid;7-Deoxyhyocholic acid;
EINECS: 201-483-2
Density: 1.128 g/cm3
Melting Point: 200-201 °C
Boiling Point: 547.1 °C at 760 mmHg
Flash Point: 298.8 °C
Solubility: 5.889mg/L(25 oC)
Appearance: White or slightly yellow powder
Hazard Symbols: HarmfulXn
Risk Codes: 36/37/38-40
Safety: 26-36/37/39-22
Transport Information:
PSA: 77.76000
LogP: 4.47790
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  • Hyodeoxycholic acidCAS NO.: 83-49-8

  • Casno:

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    Hyodeoxycholic acidCAS NO.: 83-49-8

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Chemistry

IUPAC Name: 4-[(3R,6S)-3,6-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]pentanoic acid
Synonyms of Hyodeoxycholic acid (CAS NO.83-49-8): 3-alpha,6-alpha-Dihydroxy-5-beta-cholan-24-oic acid ; 3alpha,6alpha-Dihydroxy-5beta-cholan-24-saeure ; 3alpha,6alpha-Dihydroxy-5beta-cholanoic acid ; 3alpha,6alpha-Dihydroxycholanic acid ; 5-beta-Cholanic acid-3-alpha,6-alpha-diol ; 6-alpha-Hydroxylithocholic acid ; 7-Deoxyhyocholic acid
CAS NO: 83-49-8
Molecular Formula: C24H40O4
Molecular Weight: 392.58
Molecular Structure:
EINECS: 201-483-2
H bond acceptors: 4
H bond donors: 3
Freely Rotating Bonds: 6
Polar Surface Area: 44.76 Å2
Index of Refraction: 1.543
Molar Refractivity: 109.65 cm3
Molar Volume: 347.8 cm3
Surface Tension: 46 dyne/cm
Density: 1.128 g/cm3
Flash Point: 298.8 °C
Enthalpy of Vaporization: 95.01 kJ/mol
Boiling Point: 547.1 °C at 760 mmHg
Vapour Pressure: 2.98E-14 mmHg at 25°C
Melting Point: 200-201°C
Product Categories: Natural Plant Extract
SMILES: O=C(O)CC[C@@H](C)[C@@H]4[C@]3(CC[C@H]1[C@@H](C[C@H](O)[C@@H]2C[C@H](O)CC[C@]12C)[C@@H]3CC4)C
InChI: InChI=1/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20+,21+,23-,24-/m1/s1
InChIKey: DGABKXLVXPYZII-SIBKNCMHBP
Std. InChI: InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20+,21+,23-,24-/m1/s1
Std. InChIKey: DGABKXLVXPYZII-SIBKNCMHSA-N

History

It was known that Hyodeoxycholic acid could be used to synthesize progesterone since 1939. A decade later, an analysis of hog bile showed that Hyodeoxycholic acid accounted for approximately 40% of its acid contents. In the 1950s, the East German company Jenapharm used hyodeoxycholic acid extracted from hog bile as the sole precursor for steroid synthesis because of lacking access to vegetal prescurors of steroids, like diosgenin.

In the 1980s, propensity of Hyodeoxycholic acid was investigated that it could  prevent cholesterol-induced gallstones in animals fed with a lithogenic diet. Another animal study showed that oral administration of Hyodeoxycholic acid leads to a decrease in LDL-cholesterol concentration, a strong stimulation of hepatic cholesterol biosynthesis and an excessive loss of cholesterol in feces.Hyodeoxycholic acid , unlike ursodeoxycholic acid which is an approved drug for the treatment of gallstones, is not marketed for any medical condition.

Uses

 Hyodeoxycholic acid (CAS NO.83-49-8) display different proportions  in mammalian species. It was used industrially as precursor for steroid synthesis before total synthesis became practical  because it is the main acid constituent of hog bile.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 36/37/38-40
R36/37/38: Irritating to eyes, respiratory system and skin. 
R40: Limited evidence of a carcinogenic effect.
Safety Statements: 26-36/37/39-22
S22: Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3