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83-49-8

83-49-8 structure

83-49-8 structure

Name: Hyodeoxycholic acid
Chemical Name: hyodeoxycholic acid
CAS Number: 83-49-8
Molecular Formula: C₂₄H₄₀O₄
Molecular Weight: 392.572
Catalog: API Circulatory system medication Regulating blood lipids
Create Date: 2018-02-04 08:00:00
Modify Date: 2026-06-29 19:02:56
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.

Name	hyodeoxycholic acid
Synonyms	HYODEOXYCHOLIC ACID (RG) Apigenine Impurity 2 3ALPHA, 6ALPHA-DIHYDROXY-5BETA-CHOLANIC ACID Iodeoxycholic acid 3à,6à-dihydroxy-5á-cholan-24-oic acid 3a,6a-Dihydroxy-5beta-cholan-24-oic acid 5β-CHOLANIC ACID-3α, 6α-DIOL 4-[(2R,5R,7R,8S,14R,15R)-5,8-dihydroxy-2,15-diMethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]htadecan-14-yl]pentanoic acid ALPHA-HYODESOXYCHOLIC ACID 3α, 6α-Dihydroxy-5beta-cholan-24-oic acid 3α,6α-Dihydroxy-5β-cholan-24-oic acid Hyodeoxycholic acid(HDCA) 4-(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 3α,6α-dihydroxy-5β-cholanic acid 3ALPHA,6ALPHA-DIHYDROXY-5BETA-CHOLAN-24-OIC ACID 5β-Cholan-24-Oic Acid-3α,6α-Diol (R)-4-((3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid EINECS 201-483-2 alpha-HYDROXYDEOXYCHOLIC ACID HYODEOXYCHOLANIC ACID HYDROCHOLIC ACID 3-ALPHA,6-ALPHA-DIHYDROXY-5-ALPHA-CHOLAN-24-OIC ACID 3.alpha.,6.alpha.-Dihydroxycholanic acid Hyodeoxycholic acid, >= MFCD00003681 Hyodeoxycholicacid 3a,6a-Dihydroxy-5b-Cholan-24-Oic Acid Cholan-24-oic acid, 3,6-dihydroxy-, (3α,5β,6α) Cholan-24-oic acid, 3,6-dihydroxy-,(3α,5β,6α) 7-deoxyhyocholicacid HyodeoxychoL (3R,5R,6S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-5-methylhex-5-en-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol HYODEOXYCHOLIC ACID FREE ACID Nsc60672 Pig deoxybile acid 3α,6α-Dihydroxy-5β-cholanoic acid 6-alpha-hydroxylithocholicacid 5.beta.-Cholan-24-oic acid, 3.alpha.,6.alpha.-dihydroxy Hyodeoxycholic 5BETA-CHOLAN-24 OIC ACID-3ALPHA,6ALPHA-DIOL 3alpha,6alpha-Dihydroxy-5beta-cholanoic acid 4-{5,9-dihydroxy-2,15-diMethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]htadecan-14-yl}pentanoic acid (4R)-4-((3R,5R,6S,10R,13R,17R)-3,6-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phena 3,6-dihydroxy-,(3alpha,5beta,6alpha)-cholan-24-oicaci α-Hyodeoxycholic Acid HYODEOXYCHOLIC ACID hyodeoxycholic acid GMP 5-BETA-CHOLANIC ACID-3-ALPHA, 6-ALPHA-DIOL alpha-hyodeoxycholicacid Hyodeoxycholic acid,3α,6α-Dihydroxy-5β-cholan-24-oic acid (4R)-4-((3R,5R,6S,10R,13R,17R)-3,6-dihydroxy-10,13-diMethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid 3-alpha,6-alpha-dihydroxy-5-beta-cholan-24-oicaci Hyodesoxycholic Acid (HDCA) HYODESOXYCHOLIC ACID Cholan-24-oic acid, 3,6-dihydroxy-, (3.alpha.,5.beta.,6.alpha.) Hyodeoxycholic acid //BP Deoxycholic Acid Impurity 4(α-Hyodeoxycholic Acid) 3α, 6α-dihydroxycholanic acid HDCA

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	Signaling Pathways >> GPCR/G Protein >> GPCR19 Research Areas >> Metabolic Disease Natural Products >> Steroids
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].
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].
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.

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

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

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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