Hyodeoxycholic acid

Hyodeoxycholic acid Structure
Hyodeoxycholic acid
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Common Name Hyodeoxycholic acid
CAS Number 83-49-8 Molecular Weight 392.572
Density 1.1±0.1 g/cm3 Boiling Point 547.1±25.0 °C at 760 mmHg
Molecular Formula C24H40O4 Melting Point 200-201 °C(lit.)
MSDS Chinese USA Flash Point 298.8±19.7 °C

 Use of Hyodeoxycholic acid


Hyodeoxycholic acid is a secondary bile acid formed in the small intestine by the gut flora, and acts as a TGR5 (GPCR19) agonist, with an EC50 of 31.6 µM in CHO cells.

 Names

Name hyodeoxycholic acid
Synonym More Synonyms

 Hyodeoxycholic acid Biological Activity

Description Hyodeoxycholic acid is a secondary bile acid formed in the small intestine by the gut flora, and acts as a TGR5 (GPCR19) agonist, with an EC50 of 31.6 µM in CHO cells.
Related Catalog
Target

Human Endogenous Metabolite

In Vitro Hyodeoxycholic acid is a secondary hydrophilic bile acid formed in the small intestine by the gut flora, and acts as an agonist of TGR5, with an EC50 of 31.6 µM in CHO cells[1]. Hyodeoxycholic acid (50, 100 μM) increases the expression of genes (Abca1, Abcg1, and Apoe) involved in cholesterol efflux in RAW 264.7 cells[2].
In Vivo Hyodeoxycholic acid (HDCA; 1.25% (wt/wt)) obviously decreases fat mass and increases lean mass but does not raise the serum levels of any organ toxicity markers in LDLRKO mice. Hyodeoxycholic acid inhibits atherosclerotic lesion formation in LDLRKO at multiple sites, improves plasma lipoprotein profiles, decreases plasma glucose level and intestinal cholesterol absorption efficiency and increases daily cholesterol excretion through fecal output. Hyodeoxycholic acid also improves HDL function as measured by a cholesterol efflux assay[2].
Solvent
In Vitro:

10 mM in DMSO

Solubility
1 mM 2.5473 mL 12.7366 mL 25.4732 mL
5 mM 0.5095 mL 2.5473 mL 5.0946 mL
10 mM 0.2547 mL 1.2737 mL 2.5473 mL
Animal Admin Mice[2] For atherosclerosis studies, 8-wk-old female LDLRKO mice are fed a Western diet (21% fat, 0.15% cholesterol; TD.88137) for 8 wk. One group of mice (baseline group) is euthanized at this time point for lesion measurement in the aortic root region and in the innominate artery. Atherosclerotic lesion in the whole aorta is not examined in the baseline group. The remaining mice are then divided into 2 groups and fed the following diets for another 15 wk before euthanasia: group 1, chow diet (5% fat, AIN-76A Rodent Diet); and group 2, chow diet + 1.25% (wt/wt) Hyodeoxycholic acid. For other studies, 8-wk-old female LDLRKO mice are fed a chow diet or chow diet + 1.25% Hyodeoxycholic acid for 3 wk before phenotype measurements. Food consumption and body weight are recorded weekly. Animals are measured for total body fat mass and lean mass by magnetic resonance imaging (MRI) using Bruker Minispec with software from Eco Medical Systems[2].
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Shipping Room temperature in continental US; may vary elsewhere
SMILES C[C@H](CCC(O)=O)[C@H]1CC[C@@]2([H])[C@]3([H])C[C@H](O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
References

[1]. Sato H, et al. Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies. J Med Chem. 2008 Mar 27;51(6):1831-41.

[2]. Shih DM, et al. Hyodeoxycholic acid improves HDL function and inhibits atherosclerotic lesion formation in LDLR-knockout mice. FASEB J. 2013 Sep;27(9):3805-17.

Related Molecules 3-Methyladenine | Hydrocortisone | Acetylcysteine | Tretinoin | INT-777 | Melatonine | Prostaglandin E2 | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 547.1±25.0 °C at 760 mmHg
Melting Point 200-201 °C(lit.)
Molecular Formula C24H40O4
Molecular Weight 392.572
Flash Point 298.8±19.7 °C
Exact Mass 392.292664
PSA 77.76000
LogP 5.00
Vapour Pressure 0.0±3.3 mmHg at 25°C
Index of Refraction 1.543
Storage condition Refrigerator

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
FZ2050000
CHEMICAL NAME :
5-beta-Cholan-24-oic acid, 3-alpha,6-alpha-dihydroxy-
CAS REGISTRY NUMBER :
83-49-8
BEILSTEIN REFERENCE NO. :
3218394
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C24-H40-O4
MOLECULAR WEIGHT :
392.64

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Yeast - Saccharomyces cerevisiae
DOSE/DURATION :
5600 umol/L
REFERENCE :
ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 60,192,1987

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn
Risk Phrases R36/37/38:Irritating to eyes, respiratory system and skin . R40:Limited evidence of a carcinogenic effect.
Safety Phrases S26-S36/37/39
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS FZ2050000

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