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The chemical "benzyl (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate" is a complex organic compound with a molecular formula of C31H48O3. It is a chiral molecule, meaning it has a non-superimposable mirror image, and it belongs to the class of compounds known as esters. This specific ester is derived from a long-chain hydroxy acid and a benzyl alcohol, featuring a cyclopenta[a]phenanthren-17-yl group, which is a type of polycyclic aromatic hydrocarbon structure. The compound's structure is characterized by multiple chiral centers, indicating that it has several stereoisomers. It is likely to be found in the field of organic synthesis, potentially as an intermediate in the production of pharmaceuticals or other specialty chemicals, due to its intricate structure and the presence of a hydroxyl group that can participate in further reactions.

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  • 6112-83-0 Structure
  • Basic information

    1. Product Name: benzyl (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
    2. Synonyms: benzyl (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
    3. CAS NO:6112-83-0
    4. Molecular Formula:
    5. Molecular Weight: 466.704
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 6112-83-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: benzyl (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate(CAS DataBase Reference)
    10. NIST Chemistry Reference: benzyl (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate(6112-83-0)
    11. EPA Substance Registry System: benzyl (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate(6112-83-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6112-83-0(Hazardous Substances Data)

6112-83-0 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 6112-83-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,1 and 2 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 6112-83:
(6*6)+(5*1)+(4*1)+(3*2)+(2*8)+(1*3)=70
70 % 10 = 0
So 6112-83-0 is a valid CAS Registry Number.

6112-83-0Relevant articles and documents

Novel lithocholaphanes: Syntheses, NMR, MS, and molecular modeling studies

Valkonen, Arto,Siev?nen, Elina,Ikonen, Satu,Lukashev, Nikolai V.,Donez, Pavel A.,Averin, Alexej D.,Lahtinen, Manu,Kolehmainen, Erkki

, p. 65 - 73 (2007)

Novel head-to-head lithocholaphanes 6 and 11 have been synthesized via precursors 1-5 and 7-10 with overall good yields, and characterized by 1H, 13C, and 15N NMR spectroscopy, ESI-TOF mass spectrometry, thermal analysis,

Biotinylated lithocholic acids for affinity chromatography of mammalian DNA polymerases α and β

Watanabe, Madoka,Hanashima, Shinya,Mizushina, Yoshiyuki,Yoshida, Hiromi,Oshige, Masahiko,Sakaguchi, Kengo,Sugawara, Fumio

, p. 287 - 290 (2002)

Biotinylated lithocholic acids have been synthesized. The compounds inhibited mammalian DNA polymerases α and β with dose-dependent manner. The streptavidine columns conjugated with the synthetic biotinylated compounds chromatographed both two enzymes eluted by KCl solution at the different concentrations.

Bile Acid Tethered Docetaxel-Based Nanomicelles Mitigate Tumor Progression through Epigenetic Changes

Sreekanth, Vedagopuram,Kar, Animesh,Kumar, Sandeep,Pal, Sanjay,Yadav, Poonam,Sharma, Yamini,Komalla, Varsha,Sharma, Harsh,Shyam, Radhey,Sharma, Ravi Datta,Mukhopadhyay, Arnab,Sengupta, Sagar,Dasgupta, Ujjaini,Bajaj, Avinash

, p. 5394 - 5399 (2021/02/05)

In this study, we describe the engineering of sub-100 nm nanomicelles (DTX-PC NMs) derived from phosphocholine derivative of docetaxel (DTX)-conjugated lithocholic acid (DTX-PC) and poly(ethylene glycol)-tethered lithocholic acid. Administration of DTX-PC NMs decelerate tumor progression and increase the mice survivability compared to Taxotere (DTX-TS), the FDA-approved formulation of DTX. Unlike DTX-TS, DTX-PC NMs do not cause any systemic toxicity and slow the decay rate of plasma DTX concentration in rodents and non-rodent species including non-human primates. We further demonstrate that DTX-PC NMs target demethylation of CpG islands of Sparcl1 (a tumor suppressor gene) by suppressing DNA methyltransferase activity and increase the expression of Sparcl1 that leads to tumor regression. Therefore, this unique system has the potential to improve the quality of life in cancer patients and can be translated as a next-generation chemotherapeutic.

BILE ACID-GCPII INHIBITOR CONJUGATES TO TREAT INFLAMMATORY DISEASES

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Page/Page column 39; 51, (2021/08/06)

GCPII inhibitors comprising 2-(phosphonomethyl) pentanedioic acid (2-PMPA) conjugated to a bile acid and their use for treating a disease or condition associated with elevated levels of GCPII, including inflammatory bowel disease.

Development of novel lithocholic acid derivatives as vitamin D receptor agonists

Masuno, Hiroyuki,Kazui, Yuko,Tanatani, Aya,Fujii, Shinya,Kawachi, Emiko,Ikura, Teikichi,Ito, Nobutoshi,Yamamoto, Keiko,Kagechika, Hiroyuki

, p. 3674 - 3681 (2019/07/10)

Lithocholic acid (2) was identified as the second endogenous ligand of vitamin D receptor (VDR), though its binding affinity to VDR and its vitamin D activity are very weak compared to those of the active metabolite of vitamin D3, 1α,25-dihydroxyvitamin D3 (1). 3-Acylated lithocholic acids were reported to be slightly more potent than lithocholic acid (2) as VDR agonists. Here, aiming to develop more potent lithocholic acid derivatives, we synthesized several derivatives bearing a 3-sulfonate/carbonate or 3-amino/amide substituent, and examined their differentiation-inducing activity toward human promyelocytic leukemia HL-60 cells. Introduction of a nitrogen atom at the 3-position of lithocholic acid (2) decreased the activity, but compound 6 bearing a 3-methylsulfonate group showed more potent activity than lithocholic acid (2) or its acylated derivatives. The binding of 6 to VDR was confirmed by competitive binding assay and X-ray crystallographic analysis of the complex of VDR ligand-binding domain (LBD) with 6.

Synthesis, physicochemical properties, and biological activity of bile acids 3-glucuronides: Novel insights into bile acid signalling and detoxification

Mostarda, Serena,Passeri, Daniela,Carotti, Andrea,Cerra, Bruno,Colliva, Carolina,Benicchi, Tiziana,Macchiarulo, Antonio,Pellicciari, Roberto,Gioiello, Antimo

, p. 349 - 358 (2017/12/28)

Glucuronidation is considered an important detoxification pathway of bile acids especially in cholestatic conditions. Glucuronides are less toxic than the parent free forms and are more easily excreted in urine. However, the pathophysiological significanc

snorkelling : Vs. diving in mixed micelles probed by means of a molecular bathymeter

Rodriguez-Mu?iz, Gemma M.,Gomez-Mendoza, Miguel,Nuin, Edurne,Andreu, Inmaculada,Marin, M. Luisa,Miranda, Miguel A.

, p. 10281 - 10288 (2017/12/26)

A photoactive bathymeter based on a carboxylic acid moiety covalently linked to a signalling methoxynaphthalene (MNP) fluorophore has been designed to prove the concept of snorkelling vs. diving in mixed micelles (MM). The carboxylic acid floats on the MM surface, while the MNP unit sinks deep in MM. The rate constants of MNP fluorescence quenching by iodide, which remains basically in water, consistently decrease with increasing spacer length, revealing different regions. This is associated with the distance MNP should dive in MM to achieve protection from aqueous reactants. Unequivocal proof of the exergonic photoinduced electron transfer was obtained from the UV-visible spectral signature of I3- upon steady-state photolysis. The applicability of the bathymeter was examined upon testing a family of MNP derivatives. The obtained results were validated by comparison with different lipophilicity tests: (i) a modified version of the Kow partition coefficient and (ii) the retention factor on thin layer chromatography. This concept could potentially be extended to test drugs or pharmacophores exhibiting any photoactive moiety.

Molecular Self-Assembly of Bile Acid-Phospholipids Controls the Delivery of Doxorubicin and Mice Survivability

Sreekanth, Vedagopuram,Medatwal, Nihal,Pal, Sanjay,Kumar, Sandeep,Sengupta, Sagar,Bajaj, Avinash

, p. 2649 - 2659 (2017/08/14)

Lipid composition in general determines the drug encapsulation efficacy and release kinetics from liposomes that impact the clinical outcomes of cancer therapy. We synthesized three bile acid phospholipids by conjugating the phosphocholine headgroup to th

CONJUGATED ANTI-PROLIFERATIVE DRUG NANO-PARTICLES AND PROCESS FOR PREPARATION THEREOF

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Page/Page column 17-18, (2018/04/12)

A modified bile acid-drug conjugate nanoparticle of formula R-L1-BA-L2-D or pharmaceutically acceptable salts thereof; wherein R is natural, synthetic or modified phospholipid head group,polyethylene glycol or poloxamer class of polyols, or other compatib

Glucuronidation of bile acids under flow conditions: Design of experiments and Koenigs-Knorr reaction optimization

Mostarda, Serena,Filipponi, Paolo,Sardella, Roccaldo,Venturoni, Francesco,Natalini, Benedetto,Pellicciari, Roberto,Gioiello, Antimo

, p. 9592 - 9600 (2015/02/19)

An efficient method for the C3-glucuronidation of bile acids is developed under flow conditions. A modular mesoreactor assisted flow set-up was combined with statistical design of experiments to speed up the optimization of the Koenigs-Knorr re

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