1534-35-6

Basic information

• Product Name: (4R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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: (4R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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
• CAS NO: 1534-35-6
• Molecular Formula: C₂₄H₄₀O₃
• Molecular Weight: 376.57
• Mol File: 1534-35-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 90-95 °C
• Boiling Point: 511°C at 760 mmHg
• Flash Point: 276.9°C
• Appearance: /
• Density: 1.073g/cm³
• Vapor Pressure: 1.4E-12mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: (4R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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(1534-35-6)
• EPA Substance Registry System: (4R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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(1534-35-6)

Safety Data

• Hazardous Substances Data: 1534-35-6(Hazardous Substances Data)

Usage

Uses

(3β,5β)-3-Hydroxycholan-24-oic acid has been used for the study of the activation of β1 subunit-?containing BK channels with respect to the structure of monohydroxylated bile acids.

Definition

ChEBI: A monohydroxy-5beta-cholanic acid with a beta-hydroxy substituent at position 3. The 3beta-hydroxy epimer of lithocholic acid.

InChI:InChI=1/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,23+,24-/m1/s1

Upstream product

• 104538-82-1 C₃₂H₄₆O₄ 
• 1255-51-2 methyl 3β-acetyloxy-5β-cholan-24-oate 
• 81938-70-7 methyl O-mesyllithocholate 
• 1249-75-8 methyl lithocholate 
• 434-13-9 Lithocholic acid 
• 7647-01-0 hydrogenchloride 
• 1553-56-6 dehydrolithocholic acid 
• 64-19-7 acetic acid 
• 141-52-6 sodium ethanolate 
• 106714-00-5 3β-hydroxy-5β.17βH.20ξH-cholen-(14)-oic acid-(24) 
• 861-83-6 methyl chlolate 
• 81-25-4 3α,7α,12α-trihydroxy-5β-cholanic acid 
• 91509-44-3 4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-(2,2-Dimethyl-propionyloxy)-10,13-dimethyl-7,12-dioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester 

Downstream Products

• 1249-75-8 3α-Hydroxy-5β-cholansaeure-methylester 
• 84573-10-4 N-(methoxycarbonylmethyl)-3-oxo-5β-cholan-24-oic acid amide 
• 5405-42-5 methyl 3β-hydroxy-5β-cholan-24-oate 
• 1249-75-8 4-((R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 1553-56-6 dehydrolithocholic acid 
• 434-13-9 Lithocholic acid 
• 28083-35-4 5β.14β.17βH.20ξH-cholen-(3)-oic acid-(24) 

Relevant articles and documents

Optimization of EphA2 antagonists based on a lithocholic acid core led to the identification of UniPR505, a new 3α-carbamoyloxy derivative with antiangiogenetic properties

The EphA2 receptor has been validated in animal models as new target for treating tumors depending on angiogenesis and vasculogenic mimicry. In the present work, we extended our current knowledge on structure-activity relationship (SAR) data of two related classes of antagonists of the EphA2 receptor, namely 5β-cholan-24-oic acids and 5β-cholan-24-oyl L-β-homotryptophan conjugates, with the aim to develop new antiangiogenic compounds able to efficiently prevent the formation of blood vessels. As a result of our exploration, we identified UniPR505, N-[3α-(Ethylcarbamoyl)oxy-5β-cholan-24-oyl]-L-β-homo-tryptophan (compound 14), as a submicromolar antagonist of the EphA2 receptor capable to block EphA2 phosphorylation and to inhibit neovascularization in a chorioallantoic membrane (CAM) assay.

3-MODIFIED ISO-/ISOALLO-LITHOCHOLIC ACID DERIVATIVES OR THEIR HOMO-ANALOGS FOR PREVENTING AND TREATING CLOSTRIDIOIDES DIFFICILE-ASSOCIATED DISEASES

The present invention relates to isolithocholic acid (3β-hydroxy-5β-cholan-24-oic acid) and isoallolithocholic acid (3β-hydroxy-5α-cholan-24-oic acid) together with the respective 22-homo-analogs or the deuterated analogs, which are modified in 3-position

Triplet energy management between two signaling units through cooperative rigid scaffolds

Through-bond triplet exciplex formation in donor-acceptor systems linked through a rigid bile acid scaffold has been demonstrated on the basis of kinetic evidence upon population of the triplet acceptors (naphthalene, or biphenyl) by through-bond triplet-