5BETA-CHOLESTAN-3-ONE

• CAS: 601-53-6
• Catalog Number: ACM601536
• Category: Main Products
• Molecular Weight: 386.65
• Molecular Formula: C27H46O

Case Study

5β-Cholestan-3-one as a Marine Antifouling Agent from Seaweeds

Bakar, Kamariah, et al. Journal of Applied Pharmaceutical Science 9.10 (2019): 047-053.

In this work, 5β-Cholestan-3-one (Compound 6) was isolated from Malaysian seaweeds Dictyota dichotoma and Sargassum granuliferum collected at Pulau Nunuyan Laut, Sabah. It was purified alongside other sterols (campesterol, stigmasterol, fucosterol, coprostanol, epicoprostanol) through chromatographic separation. Two assays namely, disk diffusion assay for testing antibacterial activity and crystal violet assay for testing antifouling efficacy were used in this study.
The results indicated that Gram-negative bacteria were more effectively inhibited than Gram-positive bacteria by these compounds. Fucosterol (4) and epicoprostanol (5) were the most active, showing inhibition of the two bacterial strains when compared to other tested compounds. In addition, coprostanol (1), campesterol (2), stigmasterol (3), epicoprostanol (5), and 5β-cholestan-3-one (6) were the most active as antifouling agents against the selected bacterial strains, having IC50 values in the range of 266.3 - 425.8 µg/ml.

5β-Cholestan-3-One as Key Substrate for Regioselective α-Bromination

Jastrzebska, Izabella. Journal of Chemistry 2013.1 (2013): 294107.

5β-Cholestan-3-one served as a model substrate to validate a novel α-bromination protocol involving, generation of potassium enolate with potassium hexamethyldisilazide (KHMDS) in THF/Ar atmosphere, formation of potassium enoxytriethylborate at -78°C with triethylborane, and reaction with N-bromosuccinimide (NBS) (2 equivalents) at room temperature.
Synthesis Protocol
· Enolate formation: Ketone + KHMDS (1.1 eq, 0.5M toluene) in dry THF at RT/Ar
· Borate complex: Cooled to -78°C + BEt3 (1.1 eq, 1.0M THF)
· Bromination: NBS in dry THF added → stirred at RT overnight
· Workup: Evaporated solvent; Residue washed with 3N HCl; CH2Cl2 extraction; NaHCO3 wash → MgSO4 drying → evaporation.
The bromination product of 5β-cholestane-3-one was obtained in 90% yield with high regioselectivity (single isomer). This synthetic method is superior to the direct KHMDS/NBS reaction (forming a mixture).

Custom Q&A

What is the molecular formula of 5beta-cholestan-3-one?

The molecular formula is C27H46O.

What is the molecular weight of 5beta-cholestan-3-one?

The molecular weight is 386.7 g/mol.

What is the IUPAC name of 5beta-cholestan-3-one?

The IUPAC name is (5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one.

What is the InChI of 5beta-cholestan-3-one?

The InChI is InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20-,22+,23-,24+,25+,26+,27-/m1/s1.

What is the InChIKey of 5beta-cholestan-3-one?

The InChIKey is PESKGJQREUXSRR-JDIFZLMISA-N.

What are the synonyms of 5beta-cholestan-3-one?

The synonyms are Coprostanone, Coprostan-3-one, and 5beta-cholestanone.

What is the CAS number of 5beta-cholestan-3-one?

The CAS number is 601-53-6.

How many hydrogen bond donor counts does 5beta-cholestan-3-one have?

It has 0 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does 5beta-cholestan-3-one have?

It has 1 hydrogen bond acceptor count.

What is the topological polar surface area of 5beta-cholestan-3-one?

The topological polar surface area is 17.1Ų.