Lanosterol

Base Information

• Chemical Name: Lanosterol
• CAS No.: 79-63-0
• Molecular Formula: C30H50O
• Molecular Weight: 426.726
• European Community (EC) Number: 201-214-9
• NSC Number: 60677
• UNII: 1J05Z83K3M
• DSSTox Substance ID: DTXSID1040744
• Nikkaji Number: J4.237D
• Wikipedia: Lanosterol
• Wikidata: Q414996
• RXCUI: 1442199
• Metabolomics Workbench ID: 34377
• ChEMBL ID: CHEMBL225111
• Mol file: 79-63-0.mol

Synonyms:4,4,14 alpha-trimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol;Kryptosterol;Lanosterol

Chemical Property of Lanosterol

Chemical Property:

• Vapor Pressure: 4.83E-12mmHg at 25°C
• Melting Point: 137 °C
• Refractive Index: 1.53
• Boiling Point: 498.855 °C at 760 mmHg
• PKA: 15.16±0.70(Predicted)
• Flash Point: 221.143 °C
• PSA: 20.23000
• Density: 0.988 g/cm³
• LogP: 8.47910
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 426.386166214
• Heavy Atom Count: 31
• Complexity: 767

Purity/Quality:

99% ^*data from raw suppliers

Lanosterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCC=C(C)C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C
• Isomeric SMILES: C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
• Description: Lanosterol occurs naturally in the eyes of mammals and has been shown to dissolve cataracts by revitalizing damaged cataract-causing crystallin proteins. Lanosterol’s amphipathic nature is believed to play a large role in its ability to prevent and reverse cataract formation. Lanosterol is a naturally-occurring sterol and biosynthetic precursor of several animal, fungal, and protozoan steroids, including cholesterol and ergosterol. Defects in the processing of lanosterol contribute to a wide variety of disorders, including the formation of cataracts. Similarly, certain fungicides act by blocking lanosterol processing by fungi.
• Uses: Lanosterol has been used:as a standard in HPLC for the quantification in testis samplesin S-adenosyl-L-methionine:Δ24-sterol-C-methyltransferase (SMT) assayto treat wild-type cells growing in rich medium to know its effects on Sre1 protein

Technology Process of Lanosterol

There total 43 articles about Lanosterol 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: 94.0%

O-acetyl-lanosterol (2671-68-3) → tirucallol (79-63-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; for 72h; Ambient temperature;

Reference yield: 82.0%

2,3-Oxidosqualene (14050-42-1,54910-48-4,54910-49-5,54910-50-8,55058-26-9,55058-27-0,132199-42-9,138809-21-9,147731-51-9,7200-26-2,54274-53-2,71606-52-5) → tirucallol (79-63-0)

Guidance literature:

With Trypanosoma cruzi LHY₄-[pBJ_1.22] transformant; at 25 ℃; for 24h;

DOI:10.1021/ol0160506

Reference yield: 79.0%

2,3-Oxidosqualene (14050-42-1,54910-48-4,54910-49-5,54910-50-8,55058-26-9,55058-27-0,132199-42-9,138809-21-9,147731-51-9,7200-26-2,54274-53-2,71606-52-5) → parkeol (514-45-4) + tirucallol (79-63-0) + Lanost-24-ene-3β,9α-diol (69637-82-7)

Guidance literature:

With S_. cerevisiae lanosterol-synthase Thr 384 Tyr mutant; Further Variations:; Reagents; Product distribution;

upstream raw materials:

cholesterol

2,3-Oxidosqualene

cycloartenol

O-acetyl-lanosterol

Downstream raw materials:

3β-(toluene-4-sulfonyloxy)-lanosta-8,24-diene

lanosta-8,24-dien-3-one

24(25)-epiminolanosterol

C₃₉H₅₈O₆S

Refernces

• 1、 Nicotra,Ronchetti,Russo. "Stereospecific synthesis of Δ24-sterols labelled on the 26- or 27-methyl group". . p. 541 - 548. Retrieved 1978.
• 2、 Tani, Osamu,Akutsu, Yukie,Ito, Shinji,Suzuki, Takayuki,Tateishi, Yukihiro,Yamaguchi, Tomohiko,Niimi, Tatsuya,Namatame, Ichiji,Chiba, Yasunori,Sakashita, Hitoshi,Kubota, Tomomi,Yanagi, Tetsuo,Mizukami, Shusaku,Hirayama, Kenji,Furukawa, Koji,Yamasaki, Kazuhiko. "NMR Biochemical Assay for Oxidosqualene Cyclase: Evaluation of Inhibitor Activities on Trypanosoma cruzi and Human Enzymes". . p. 5047 - 5053. Retrieved 2018/05/29.
• 3、 Chang, Cheng-Hsiang,Chen, Yi-Chi,Tseng, Sheng-Wei,Liu, Yuan-Ting,Wen, Hao-Yu,Li, Wen-Hsuan,Huang, Chiao-Ying,Ko, Cheng-Yu,Wang, Tsai-Ting,Wu, Tung-Kung. "The cysteine 703 to isoleucine or histidine mutation of the oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae generates an iridal-type triterpenoid". . p. 2376 - 2381,6. Retrieved 2020/08/20.