Bilobol

Base Information

• Chemical Name: Bilobol
• CAS No.: 22910-86-7
• Molecular Formula: C21H34 O2
• Molecular Weight: 318.5
• Hs Code.: 2907299090
• UNII: NSK9KWM3T6
• ChEMBL ID: CHEMBL461628
• DSSTox Substance ID: DTXSID90872874
• Metabolomics Workbench ID: 53010
• Nikkaji Number: J167.340H
• Wikidata: Q4913564
• Wikipedia: Bilobol
• Mol file: 22910-86-7.mol

Synonyms:5-(8-pentadecenyl)-1,3-benzenediol;bilobol

Chemical Property of Bilobol

Chemical Property:

• Vapor Pressure: 5.37E-09mmHg at 25°C
• Melting Point: 32 °C
• Boiling Point: 457.7°C at 760 mmHg
• PKA: 9.55±0.10(Predicted)
• Flash Point: 199.3°C
• PSA: 40.46000
• Density: 0.97g/cm³
• LogP: 6.67840
• XLogP3: 8.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 318.255880323
• Heavy Atom Count: 23
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC=CCCCCCCCC1=CC(=CC(=C1)O)O
• Isomeric SMILES: CCCCCC/C=C\CCCCCCCC1=CC(=CC(=C1)O)O

Technology Process of Bilobol

There total 8 articles about Bilobol 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:

5-(pentadec-8-ynyl)resorcinol dimethyl ether (52483-34-8) → bilobol (22910-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / H₂, quinoline / 5percent Pd/CaCO₃ / cyclohexane / 1 h / 760 Torr

2: 92 percent / MeMgI / 0.25 h / 100 - 165 °C

With quinoline; methyl magnesium iodide; hydrogen; Lindlar's catalyst; In cyclohexane;

DOI:10.1021/ja00156a004

Reference yield:

1-octynyllithium (21433-45-4) → bilobol (22910-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 7.5 h / Heating

3: 96 percent / 9-iodo-BBN / hexane / Ambient temperature

With 9-iodo-BBN; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane;

DOI:10.1021/jo962423i

Reference yield:

n-octyne (629-05-0) → bilobol (22910-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi, hexamethylphosphoramide / 1.) hexane, 0 deg C, 30 min, 2.) THF, RT, 12 h

2: 87 percent / H₂, quinoline / 5percent Pd/CaCO₃ / cyclohexane / 1 h / 760 Torr

3: 92 percent / MeMgI / 0.25 h / 100 - 165 °C

With quinoline; N,N,N,N,N,N-hexamethylphosphoric triamide; methyl magnesium iodide; n-butyllithium; hydrogen; Lindlar's catalyst; In cyclohexane;

DOI:10.1021/ja00156a004

upstream raw materials:

3,5-dimethoxyphenol

3,5-dimethoxyphenyl trifluoromethanesulfonate

1-octynyllithium

6-hepten-1-yl iodide

Downstream raw materials:

heptanal

5-n-pentadecylresorcinol

1,3-dimethoxy-5-pentadecylbenzene

Refernces

Antitumor principles from Ginkgo biloba L.

10.1248/cpb.35.3016

This research aimed to isolate and identify antitumor principles from Ginkgo biloba L., focusing on their effectiveness against Sarcoma 180 ascites in mice. The study successfully isolated seven long-chain phenols, among which anacardic acid (Ib), bilobol (IIa), and cardanol (IIIa) demonstrated significant antitumor activity, with effectiveness rated as (+++) for Ib, (++) for IIa, and (+++) for IIIa at a dosage of 40 mg/kg/day. The compounds were further purified using high-performance liquid chromatography (HPLC) and characterized through spectral data analysis, which included ultraviolet, infrared, nuclear magnetic resonance, and mass spectrometry. The study concluded that the antitumor activity against Sarcoma 180 ascites does not require the carboxyl group, in contrast to the antimicrobial activity which does.