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Purity: =99.98%
Hyocholic Acid (3α,6α,7α-trihydroxy-5β-cholan-24-oic acid) is a biliary acid found mainly in pig as well as in human urine at low concentrations, in particular, in urine samples from patients with cholestasis. Hyocholic Acid can promote GLP-1 secretion via activating TGR5 and inhibiting FXR in enteroendocrine cells. It is known for its exceptional resistance to type 2 diabetes . Hyocholic acid differs from the primary bile acids found in humans by having a third hydroxyl group in the α-conformation at the 6-position, unlike cholic acid, which has a 12-hydroxyl, and chenodeoxycholic acid which has neither a 6- or 12-hydroxyl. It also differs from the muricholic acids found in rodents, as they are 6β-hydroxylated, and can have the 7-hydroxyl in either the α- or β- positions, forming α- or β-muricholic acids.
| Targets |
TGR5; FXR
|
|---|---|
| ln Vitro |
In STC-1 and NCI-H716 cells, HCA (25 and 50 μM, 24 h) increases GLP-1 protein secretion[3]. In STC-1 and NCI-H716 cells, HCA (25 and 50 μM, 24 h) increases the transcription of the proglucagon gene[3].
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| ln Vivo |
Pigs' blood glucose rise brought on by BA depletion is suppressed by hyocholic acid (20 mg/kg, po)[3]. In diabetic mouse models, hydroxycholic acid (100 mg/kg/day, po) enhances serum fasting GLP-1 secretion and glucose homeostasis [3].
Hyocholic acid (HCA) and its derivatives are found in trace amounts in human blood but constitute approximately 76% of the bile acid (BA) pool in pigs, a species known for its exceptional resistance to type 2 diabetes. Here, we show that BA depletion in pigs suppressed secretion of glucagon-like peptide-1 (GLP-1) and increased blood glucose levels. HCA administration in diabetic mouse models improved serum fasting GLP-1 secretion and glucose homeostasis to a greater extent than tauroursodeoxycholic acid. HCA upregulated GLP-1 production and secretion in enteroendocrine cells via simultaneously activating G-protein-coupled BA receptor, TGR5, and inhibiting farnesoid X receptor (FXR), a unique mechanism that is not found in other BA species. We verified the findings in TGR5 knockout, intestinal FXR activation, and GLP-1 receptor inhibition mouse models. Finally, we confirmed in a clinical cohort, that lower serum concentrations of HCA species were associated with diabetes and closely related to glycemic markers.[3] |
| Cell Assay |
Western Blot Analysis[3]
Cell Types: NCI-H716 cells Tested Concentrations: 50 μM Incubation Duration: 48 h Experimental Results: Inhibited the high expression of SHP (small heterodimer partner) induced by the FXR agonist. |
| Animal Protocol |
Animal/Disease Models: BA depletion pigs[3]
Doses: 20 mg/kg Route of Administration: Oral administration (po) Experimental Results: Attenuated the increased blood glucose levels corresponding with GLP-1 decrease. Animal/Disease Models: db/db model, and the high-fat diet and streptozotocin (HFD+STZ) induced diabetic model[3] Doses: 100 mg/kg/day Route of Administration: Oral administration (po) Experimental Results: Improved oral glucose tolerances shown by lower glucose levels. Increased circulating active GLP- 1 levels and fasting insulin levels. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
Hyocholic acid has known human metabolites that include hyocholic acid 24-O-glucuronide and hyocholic acid 6-O-glucuronide. |
| References |
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| Additional Infomation |
Hyocholic acid is a trihydroxy-5beta-cholanic acid in which the three hydroxy substituents are located at the 3alpha-, 6alpha- and 7alpha-positions. It has a role as a mouse metabolite, a human urinary metabolite and a rat metabolite. It is a C24-steroid, a 6alpha-hydroxy steroid, a 7alpha-hydroxy steroid and a member of muricholic acids. It is a conjugate acid of a hyocholate.
Hyocholic acid has been reported in Homo sapiens with data available. |
| Molecular Formula |
C24H40O5
|
|---|---|
| Molecular Weight |
408.5714
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| Exact Mass |
408.287
|
| CAS # |
547-75-1
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| Related CAS # |
Hyocholic Acid-d4;Hyocholic Acid-d5
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| PubChem CID |
92805
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| Appearance |
White to light yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
565.7±40.0 °C at 760 mmHg
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| Melting Point |
188-189ºC
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| Flash Point |
310.0±23.8 °C
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| Vapour Pressure |
0.0±3.5 mmHg at 25°C
|
| Index of Refraction |
1.558
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| LogP |
3.82
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
29
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| Complexity |
637
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| Defined Atom Stereocenter Count |
11
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| SMILES |
C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]4(C)CC[C@H](C[C@H]4[C@H]([C@H]3O)O)O
|
| InChi Key |
DKPMWHFRUGMUKF-KWXDGCAGSA-N
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| InChi Code |
InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22+,23-,24-/m1/s1
|
| Chemical Name |
(4R)-4-[(3R,5R,6R,7S,8S,9S,10R,13R,14S,17R)-3,6,7-trihydroxy-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 |
gamma-Muricholic acid; Iocholic acid; 3alpha,6alpha,7alpha-Trihydroxy-5beta-cholan-24-oic acid; (4R)-4-[(3R,5R,6R,7S,8S,9S,10R,13R,14S,17R)-3,6,7-trihydroxy-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; 2H5H0Q47FL; CHEBI:81244;
|
| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~62.5 mg/mL (~152.97 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4476 mL | 12.2378 mL | 24.4756 mL | |
| 5 mM | 0.4895 mL | 2.4476 mL | 4.8951 mL | |
| 10 mM | 0.2448 mL | 1.2238 mL | 2.4476 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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