10,13-Dimethyl-17-(6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Base Information

• Chemical Name: 10,13-Dimethyl-17-(6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS No.: 601-57-0
• Molecular Formula: C27H44 O
• Molecular Weight: 384.646
• Hs Code.: 29142900
• NSC Number: 134926,63000
• DSSTox Substance ID: DTXSID50862271
• Wikidata: Q105187611
• Mol file: 601-57-0.mol

Synonyms:10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;4-Cholestenone;9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one;NSC-63000;NSC-134926;delta-4-Cholesten-3-one;NCIOpen2_008122;CERAPP_28175;SCHEMBL1688732;DTXSID50862271;CHEBI:180953;NYOXRYYXRWJDKP-UHFFFAOYSA-N;NSC63000;BBL028484;NSC134926;STL372847;AKOS025116968;17-(1,5-dimethylhexyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;VS-08793;FT-0618275;17-(1,5-DI-ME-HEXYL)-10,13-DI-ME-TETRADECAHYDRO-CYCLOPENTA(A)PHENANTHREN-3-ONE;17-(1,5-DIMETHYL-HEXYL)-DIMETHYL-TETRADECAHYDRO-CYCLOPENTA(A)PHENANTHREN-3-ONE

Chemical Property of 10,13-Dimethyl-17-(6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Chemical Property:

• Appearance/Colour: white to light yellow crystals or powder
• Vapor Pressure: 1.78E-09mmHg at 25°C
• Melting Point: 79-82 °C
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 482.7 °C at 760 mmHg
• Flash Point: 247.7 °C
• PSA: 17.07000
• Density: 0.98 g/cm³
• LogP: 7.59690
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Sparingly), Methanol (Slightly, Heated)
• Water Solubility.: <0.5 g/L
• XLogP3: 8.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 384.339216023
• Heavy Atom Count: 28
• Complexity: 630

Purity/Quality:

98%,99%, ^*data from raw suppliers

Δ4-Cholesten-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
• Description: Cholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol. It decreases TGF-β-induced Smad2 phosphorylation and TGF-β expression and prevents inhibition of DNA synthesis by TGF-β in Mv1Lu cells when used at a concentration of 50 μg/ml. Increased fecal excretion of cholestenone is correlated with an increased risk of colorectal cancer. Cholestenone reduces serum cholesterol levels in a variety of animal models but is toxic to rats when administered at doses of 700-1,000 mg/kg per day, inducing hypertrophy in and reducing the activity of the adrenal gland. It has been used as synthetic intermediate in the synthesis of steroids.
• Uses: 4-Cholesten-3-one is used as a chiral building block for proteomics research. It is an intestinal metabolite of cholesterol and exhibits an anti-obesity effect on animals.

Technology Process of 10,13-Dimethyl-17-(6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

There total 202 articles about 10,13-Dimethyl-17-(6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

cholesterol (57-88-5) → Cholest-4-en-3-one (601-57-0)

Guidance literature:

With aluminum tris(iso-propoxide); In cyclohexanone; toluene; for 10h; Reflux;

DOI:10.1016/j.bmcl.2014.05.064

Reference yield: 98.0%

cholesterol (57-88-5) → Cholest-4-en-3-one (601-57-0) + 4-cholestene-3,6-dione (54339-68-3,984-84-9) + cholest-4-ene-6β-hydroperoxy-3-one (2207-76-3) + 6α-hydroxy-cholest-4-en-3-one (570-90-1)

Guidance literature:

With cholesterol oxidase; In isopropyl alcohol; at 37 ℃; for 24h; Further byproducts given. Yields of byproduct given;

DOI:10.1021/ja962258o

Reference yield: 98.0%

Cholest-5-en-3-one (601-54-7) → Cholest-4-en-3-one (601-57-0) + 4-cholestene-3,6-dione (54339-68-3,984-84-9) + cholest-4-ene-6β-hydroperoxy-3-one (2207-76-3) + 6α-hydroxy-cholest-4-en-3-one (570-90-1)

Guidance literature:

With cholesterol oxidase; In isopropyl alcohol; at 37 ℃; for 24h; Further byproducts given. Yields of byproduct given;

DOI:10.1021/ja962258o

upstream raw materials:

pyridine

4β-bromo-5β-cholestan-3-one

2,4,6-trimethyl-pyridine

2α-bromo-5α-cholestan-3-one

Downstream raw materials:

4-Methylpentanoic acid

Progesterone

Androstenedione

Cholestanol

Refernces

• 1、 Kocovsky, Pavel,Srogi, Jiri,Pour, Milan,Gogoll, Adolf. "Corner Opening of Cyclopropanes by Mercury(II) and Thallium(III) and Transmetalation of the Intermediate Organomercurials. A Novel, Stereoselective Approach to Cyclobutanes and Cyclopropanes". . p. 186 - 197. Retrieved 1994.
• 2、 Fauve, A.,Kergomard, A.. "MULTIFUNCTIONAL CATALYSIS-X."TAILOR-MADE" CATALYSTS FOR THE ISOMERISATION OF Δ-5 CHOLESTENONE". . p. 1697 - 1702. Retrieved 1981.
• 3、 Kass,Sampson. "The importance of GLU361 position in the reaction catalyzed by cholesterol oxidase.". . p. 2663 - 2668. Retrieved 1998.
• 4、 Lipshutz, Bruce H.,Mollard, Paul,Lindsley, Craig,Chang, Virginia. "Cyclo-SEM: A new carbonyl protecting group". . p. 1873 - 1876. Retrieved 1997.
• 5、 Dewangan, Lakshita,Korram, Jyoti,Karbhal, Indrapal,Nagwanshi, Rekha,Jena, Vinod K.,Satnami, Manmohan L.. "A colorimetric nanoprobe based on enzyme-immobilized silver nanoparticles for the efficient detection of cholesterol". . p. 42085 - 42095. Retrieved 2019.
• 6、 Ou, Xin,Tan, Xingrong,Liu, Xiaofang,Chen, Hongmei,Fan, Yu,Chen, Shihong,Wei, Shaping. "A cathodic luminol-based electrochemiluminescence biosensor for detecting cholesterol using 3D-MoS2-PANI nanoflowers and Ag nanocubes for signal enhancement". . p. 66409 - 66415. Retrieved 2015.
• 7、 Linburg,Cox,Spencer. "". . p. 716. Retrieved 1951.
• 8、 Négrel, Sophie,Brunel, Jean Michel. "Efficient and selective microwave Oppenauer oxidation of sterol derivatives". . . Retrieved 2021/02/05.
• 9、 Bus, Katarzyna,Ofiara, Karol,Sitkowski, Jerzy,Szterk, Arkadiusz,Zmys?owski, Adam. "Synthesis and search for 3β,3′β-disteryl ethers after high-temperature treatment of sterol-rich samples". . . Retrieved 2020/06/08.