Deoxycholic acid | deoxycholate | cholanoic acid | CAS#83-44-3

MedKoo Cat#: 510266 | Name: Deoxycholic Acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Deoxycholic acid, also known as deoxycholate, cholanoic acid, and 3α,12α-dihydroxy-5β-cholanate, is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. Deoxycholic acid has been used since its discovery in various fields of human medicine. In the human body deoxycholic acid is used in the emulsification of fats for the absorption in the intestine. Outside the body it is used in experimental basis of cholagogues and is also in use to prevent and dissolve gallstones.

Chemical Structure

Deoxycholic Acid

CAS#83-44-3

Theoretical Analysis

MedKoo Cat#: 510266

Name: Deoxycholic Acid

CAS#: 83-44-3

Chemical Formula: C24H40O4

Exact Mass: 392.2927

Molecular Weight: 392.57

Elemental Analysis: C, 73.43; H, 10.27; O, 16.30

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 Weeks
25g	USD 450.00	2 Weeks

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Related CAS #

No Data

Synonym

Deoxycholic acid; Cholanoic Acid; Desoxycholic acid; Deoxycholate; Cholerebic; DCA; NSC 8797; NSC8797; NSC-8797;

IUPAC/Chemical Name

(R)-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

InChi Key

KXGVEGMKQFWNSR-LLQZFEROSA-N

InChi Code

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

SMILES Code

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

Appearance

white to off-white solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Deoxycholic acid has been used since its discovery in various fields of human medicine. In the human body deoxycholic acid is used in the emulsification of fats for the absorption in the intestine. It has, in some countries (including Switzerland) been licensed as an emulsifier in food industry, but it is no longer common. Outside the body it is used in experimental basis of cholagogues and is also in use to prevent and dissolve gallstones. Sodium deoxycholate, the sodium salt of deoxycholic acid, is frequently used in mesotherapy injections, mixed with phosphatidylcholine. In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins. The critical micelle concentration for deoxycholic acid is approximately 2.4-4 mM. Sodium deoxycholate, the sodium salt of deoxycholic acid, is often used as a biological detergent to lyse cells and solubilise cellular and membrane components. Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology. They also have found application in microlithography as photoresistant components. There is promising research to suggest the use of deoxycholic acid may be a viable alternative to surgical excision in the treatment of lipomas. (http://en.wikipedia.org/wiki/Deoxycholic_acid)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Deoxycholic acid is specifically responsible for activating the G protein-coupled bile acid receptor TGR5 that stimulates brown adipose tissue (BAT) thermogenic activity.

In vitro activity:

Deoxycholic acid was shown to have a malignant induction effect, activating the IL-6/STAT3 pathway, and promoting the upregulation of KLF4, OCT4, Nanog, Bcl-xL, and other genes. It also has the potential to induce the transformation of EAC cells into CSCs, improving the antiapoptosis ability of tumors, and further increasing the malignancy of EAC. Reference: Technol Cancer Res Treat. 2020; 19: 1533033820945302. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7469721/

In vivo activity:

Compared with the empty vector, overexpression of miR-92b-3p significantly increased the cell proliferation, whereas DCA (deoxycholic acid) treatment could significantly attenuated miR-92b-3p-mediated tumor growth (Fig. 7a). Consistently, the tumors excised from mice with miR-92b-3p-overexpressing cells increased weights compared with those excised from mice inoculated with the empty vector, even when treated with DCA (Fig. 7b, c). Reference: Oncogene. 2020; 39(26): 4983–5000. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7314665/

	Solvent	mg/mL	mM
Solubility
	DMSO	66.0	168.12
	DMF	30.0	76.42
	DMF:PBS (pH 7.2) (1:1)	0.5	1.27
	Ethanol	40.0	101.89
	Water	1.0	2.55

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 392.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Chen M, Ye A, Wei J, Wang R, Poon K. Deoxycholic Acid Upregulates the Reprogramming Factors KFL4 and OCT4 Through the IL-6/STAT3 Pathway in Esophageal Adenocarcinoma Cells. Technol Cancer Res Treat. 2020 Jan-Dec;19:1533033820945302. doi: 10.1177/1533033820945302. PMID: 32869704; PMCID: PMC7469721. 2. Lin R, Zhan M, Yang L, Wang H, Shen H, Huang S, Huang X, Xu S, Zhang Z, Li W, Liu Q, Shi Y, Chen W, Yu J, Wang J. Deoxycholic acid modulates the progression of gallbladder cancer through N6-methyladenosine-dependent microRNA maturation. Oncogene. 2020 Jun;39(26):4983-5000. doi: 10.1038/s41388-020-1349-6. Epub 2020 Jun 8. PMID: 32514152; PMCID: PMC7314665.

In vitro protocol:

In vivo protocol:

1. Lin R, Zhan M, Yang L, Wang H, Shen H, Huang S, Huang X, Xu S, Zhang Z, Li W, Liu Q, Shi Y, Chen W, Yu J, Wang J. Deoxycholic acid modulates the progression of gallbladder cancer through N6-methyladenosine-dependent microRNA maturation. Oncogene. 2020 Jun;39(26):4983-5000. doi: 10.1038/s41388-020-1349-6. Epub 2020 Jun 8. PMID: 32514152; PMCID: PMC7314665.

1: Hill MJ. The ratio of lithocholic to deoxycholic acid in faeces: a risk factor in colorectal carcinogenesis. Eur J Cancer Prev. 1991 Oct;1 Suppl 2:75-8. Review. PubMed PMID: 1842737. 2: Marcus SN, Heaton KW. Deoxycholic acid and the pathogenesis of gall stones. Gut. 1988 Apr;29(4):522-33. Review. PubMed PMID: 3286385; PubMed Central PMCID: PMC1433553. 3: Owen RW, Thompson MH, Hill MJ, Wilpart M, Mainguet P, Roberfroid M. The importance of the ratio of lithocholic to deoxycholic acid in large bowel carcinogenesis. Nutr Cancer. 1987;9(2-3):67-71. Review. PubMed PMID: 3550718. 4: LaRusso NF, Szczepanik PA, Hofmann AF. Effect of deoxycholic acid ingestion on bile acid metabolism and biliary lipid secretion in normal subjects. Gastroenterology. 1977 Jan;72(1):132-40. Review. PubMed PMID: 318580.