Hyodeoxycholic acid

Hyodeoxycholic acid
Names
IUPAC name
3α,6α-Dihydroxy-5β-cholan-24-oic acid
Systematic IUPAC name
(4R)-4-[(1R,3aS,3bS,5S,5aR,7R,9aR,9bS,11aR)-5,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.349
UNII
  • 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 N
    Key: DGABKXLVXPYZII-SIBKNCMHSA-N N
  • 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
    Key: DGABKXLVXPYZII-SIBKNCMHBP
  • 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
Properties
C24H40O4
Molar mass 392.58 g/mol
Density ? g/cm3
Melting point 200 to 201 °C (392 to 394 °F; 473 to 474 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Hyodeoxycholic acid, also known as 3α,6α-Dihydroxy-5β-cholan-24-oic acid or HDCA, is a secondary bile acid, one of the metabolic byproducts of intestinal bacteria. It differs from deoxycholic acid in that the 6α-hydroxyl is in the 12 position in the former. The 6α-hydroxyl group makes HDCA a hydrophilic acid, a property it shares with hyocholic acid. HDCA is present in mammalian species in different proportions. It is the main acid constituent of hog bile, and for this reason it was used industrially as precursor for steroid synthesis before total synthesis became practical.