Hyodeoxycholic acid

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

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.

 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.

Hazard Codes: Xn
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