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Documenti

30960

Sigma-Aldrich

Deoxycholic acid

≥99.0% (T)

Sinonimo/i:

3α,12α-Dihydroxy-5β-cholanic acid, 7-Deoxycholic acid, Desoxycholic acid

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About This Item

Formula empirica (notazione di Hill):
C24H40O4
Numero CAS:
83-44-3
Peso molecolare:
392.57
Beilstein:
3219882
Numero CE:
201-478-5
Numero MDL:
MFCD00003673
Codice UNSPSC:
12352106
ID PubChem:
329753610
NACRES:
NA.77

Origine biologica

ox bile

Descrizione

anionic

Saggio

≥99.0% (T)

Forma fisica

powder

Attività ottica

[α]20/D +54±1°, c = 1% in ethanol

PM

392.57 g/mol

Impurezze

≤1% cholic acid (TLC)

Punto di fusione

170-175 °C
171-174 °C (lit.)

Gruppo funzionale

carboxylic acid

Stringa SMILE

C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C

InChI

1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
KXGVEGMKQFWNSR-LLQZFEROSA-N

Informazioni sul gene

human ... ATIC(471)

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Categorie correlate

Descrizione generale

Deoxycholic acid is an amphiphilic molecule and an important constituent of bile acid. It contains hydroxyl groups substituted at the 3α and 12α positions and a carboxyl group towards the end of the branched-chain. These moieties contribute to the hydrophilic nature of the molecule and the hydrophobic cyclopentanophenanthrene forms its center.

Applicazioni

Deoxycholic acid has been used as:
  • a hyphal-inhibitory compound in an ex vivo assay to study the hyphal morphogenesis of Candida albicans in the gastrointestinal tract
  • an internal standard to estimate the toxin concentration in the cell pellet
  • a bile acid (BA) standard to quantitatively measure BA in various samples from treated mice by ultra-performance liquid chromatography triple quadrupole mass spectrometry

Azioni biochim/fisiol

Deoxycholic acid, due to its amphiphilicity, significantly helps to solubilize, emulsify, and absorb fat, vitamins, and cholesterol in the body. High levels of intestinal deoxycholic acid might cause colorectal cancer by inducing oxidative stress and leading to DNA damage. It acts as an oncogene and pro-tumor factor.

Altre note

For the solubilization of the β-adrenergic receptor

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302,H315,H319,H335

Classi di pericolo

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Preparation and characterizations of a novel deoxycholic acid-O-carboxymethylated chitosan-folic acid conjugates and self-aggregates
Wang F, et al.
Carbohydrate Polymers, 84, 1192-1200 (2011)
E Nedivi et al.
The Journal of biological chemistry, 259(9), 5803-5808 (1984-05-10)
Agonist, but not antagonist, protects the beta-adrenergic receptor from inactivation during solubilization in deoxycholate. Protection is apparently due to locking of the agonist in the receptor, a high affinity interaction induced or stabilized by this detergent. The guanyl nucleotide-binding protein
Jeffery L Smith et al.
Hepatology (Baltimore, Md.), 39(6), 1673-1682 (2004-06-09)
Focal biliary cirrhosis causes significant morbidity and mortality in cystic fibrosis (CF). Although the mechanisms of pathogenesis remain unclear, bile acids have been proposed as potential mediators of liver injury. This study examined bile acid composition in CF and assessed
J Stadler et al.
Cancer letters, 38(3), 315-320 (1988-01-01)
Rectal biopsies and fecal collections were obtained from a consecutive series of 34 outpatients prior to colonoscopy at a gastroenterology clinic. Subsequently, 14 were found to have no colonic pathology, 13 had adenomatous polyps, (3 of those had a previous
Lotta K Stenman et al.
American journal of physiology. Gastrointestinal and liver physiology, 304(3), G227-G234 (2012-12-04)
Impairment of gut barrier is associated with a fat-rich diet, but mechanisms are unknown. We have earlier shown that dietary fat modifies fecal bile acids in mice, decreasing the proportion of ursodeoxycholic acid (UDCA) vs. deoxycholic acid (DCA). To clarify
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