Cholesterol-d7

Base Information

• Chemical Name: Cholesterol-d7
• CAS No.: 83199-47-7
• Molecular Formula: C₂₇H₄₆O
• Molecular Weight: 393.606
• DSSTox Substance ID: DTXSID50415625
• Nikkaji Number: J2.126.976J
• Wikidata: Q72460685
• Mol file: 83199-47-7.mol

Synonyms:Cholesterol-d7;83199-47-7;7alpha-Hydroxy Cholesterol-D7;Cholesterol(d7);(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol;Cholesterol-25,26,26,26,27,27,27-d7;cholest-5-en-3beta-ol(d7);d7-cholesterol;Cholesterol_d7;Cholesterol D7;HY-N0322S;DTXSID50415625;7 alpha -Hydroxy Cholesterol-D7;CHEBI:172955;LMST01010093;AKOS030242857;CS-T-51105;AS-82224;CS-0093063;D98037;Cholesterol-25,26,26,26,27,27,27-d7, 99 atom % D, 98% (CP);(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-((2)H?)methyl(6,7,7,7-(2)H?)heptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

Chemical Property of Cholesterol-d7

Chemical Property:

• Vapor Pressure: 2.95E-11mmHg at 25°C
• Melting Point: 141-143oC
• Boiling Point: 480.6°C at 760 mmHg
• Flash Point: 209.3°C
• PSA: 20.23000
• Density: 1g/cm³
• LogP: 7.38870
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
• XLogP3: 8.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 393.398803308
• Heavy Atom Count: 28
• Complexity: 591

Purity/Quality:

99% ^*data from raw suppliers

Cholesterol-d7 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: [2H]C([2H])([2H])C([2H])(CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C([2H])([2H])[2H]
• Description: Cholesterol-d7 is intended for use as an internal standard for the quantification of cholesterol by GC- or LC-MS. Cholesterol is a major sterol produced in mammalian cells that is required for cell viability and proliferation. It is a component of mammalian cell membranes that interacts with membrane phospholipids, sphingolipids, and proteins to influence their behavior. Cholesterol is a precursor of steroid hormones, bile acids, and the active form of vitamin D. Impaired cholesterol homeostasis is related to development of various diseases including fatty liver, diabetes, gallstones, dyslipidemia, atherosclerosis, heart attack, and stroke.
• Uses: Cholesterol-d7 is a labelled Cholesterol (C432501). Cholesterol-d7 is the principal sterol of the higher animals. Cholesterol-d7 was found in all body tissues, especial in the brain, spinal cord, and in animal fats or oils. Cholesterol-d7 is the main constituent of gallstones. Cholesterol-d7 can be used as a practical tracer for studies of cholesterol metabolism in humans. Labelled Cholesterol (C432501). Cholesterol is the principal sterol of the higher animals. Cholesterol was found in all body tissues, especial in the brain, spinal cord, and in animal fats or oils. Cholesterol is the main constituent of gallstones. Labelled Cholesterol can be used as a practical tracer for studies of cholesterol metabolism in humans

Technology Process of Cholesterol-d7

There total 15 articles about Cholesterol-d7 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%

6β-methoxy-3α,5-cyclo-5α-25,26,26,26,27,27,27-d7-cholestane (288374-36-7) → (25,26,26,26,27,27,27-2H7)-cholesterol (83199-47-7)

Guidance literature:

With trifluorormethanesulfonic acid; water; In 1,4-dioxane; for 1.5h; Heating;

DOI:10.1002/1099-1344(200007)43:8<773::AID-JLCR361>3.0.CO;2-G

Reference yield: 87.0%

cholester-23,23,24,24,25,26,26,26,27,27,27-d11-3β-ol THP ether → cholester-23,23,24,24,25,26,26,26,27,27,27-d11-3β-ol (83199-47-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 48h;

DOI:10.1016/j.chemphyslip.2013.08.003

Reference yield:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → (25,26,26,26,27,27,27-2H7)-cholesterol (83199-47-7)

Guidance literature:

Multi-step reaction with 8 steps

1: DIPEA; LiCl / acetonitrile / 72 h / 20 °C

2: H₂ / Pd/C / ethyl acetate / 6 h / 20 °C

3: 12 g / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

4: PCC; AcOK; celite / CH₂Cl₂ / 1 h / 20 °C

5: tetrahydrofuran / 1.5 h / -78 - 20 °C

6: 6.3 g / Et₃N / CH₂Cl₂ / 2 h / 0 °C

7: 65.9 percent / NaBH₄ / dimethylsulfoxide / 3 h / 90 °C

8: 99 percent / triflic acid; H₂O / dioxane / 1.5 h / Heating

With sodium tetrahydroborate; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; Celite; water; hydrogen; potassium acetate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetonitrile; 1: Wittig reaction / 2: Catalytic hydrogenation / 3: Reduction / 4: Oxidation / 5: Grignard addition / 6: Condensation / 7: Reduction / 8: Hydrolysis;

DOI:10.1002/1099-1344(200007)43:8<773::AID-JLCR361>3.0.CO;2-G

upstream raw materials:

6β-methoxy-3α,5-cyclo-5α-25,26,26,26,27,27,27-d7-cholestane

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde

ethyl 6β-methoxy-3α,5-cyclocholanate

(22E)-ethyl 6β-methoxy-3α,5-cyclochol-22-enate

Refernces

• 1、 Baek, Dong Jae,Bittman, Robert. "Synthesis of cholesterol analogs having varying length alkyl side chains including cholesterol-23, 23, 24, 24, 25, 26, 26, 26, 27, 27, 27-d11 as probes of cholesterol's functions and properties". . p. 99 - 104. Retrieved 2013.