Ferruginol

Base Information

• Chemical Name: Ferruginol
• CAS No.: 514-62-5
• Molecular Formula: C20H30 O
• Molecular Weight: 286.458
• UNII: N2CMM6X37M
• DSSTox Substance ID: DTXSID20331722
• Nikkaji Number: J17.558G
• Wikipedia: Ferruginol
• Wikidata: Q3743828
• Metabolomics Workbench ID: 69094
• ChEMBL ID: CHEMBL197308
• Mol file: 514-62-5.mol

Synonyms:ferruginol

Chemical Property of Ferruginol

Chemical Property:

• Vapor Pressure: 1.41E-06mmHg at 25°C
• Melting Point: 56-57℃
• Boiling Point: 388.1°Cat760mmHg
• PKA: 10.89±0.60(Predicted)
• Flash Point: 175.1°C
• PSA: 20.23000
• Density: 0.988g/cm³
• LogP: 5.54580
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 286.229665576
• Heavy Atom Count: 21
• Complexity: 385

Purity/Quality:

99%, ^*data from raw suppliers

Ferruginol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C1=C(C=C2C(=C1)CCC3C2(CCCC3(C)C)C)O
• Isomeric SMILES: CC(C)C1=C(C=C2C(=C1)CC[C@@H]3[C@@]2(CCCC3(C)C)C)O
• Uses: Ferruginol can be used for its antibacterial activities.

Technology Process of Ferruginol

There total 115 articles about Ferruginol 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: 100.0%

(4aS,10aS)-1,2,3,4,4a,9,10,10a-Octahydro-6-hydroxy-7-isopropenyl-1,1,4a-trimethylphenanthrene (303962-64-3) → ferruginol (514-62-5)

Guidance literature:

With hydrogen; 5percent Pd/C; In ethyl acetate; at 20 ℃; for 24h;

DOI:10.1039/b003497p

Reference yield: 99.0%

ferruginol acetate (15340-79-1) → ferruginol (514-62-5)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1021/ol4003652

Reference yield: 97.0%

(+/-)-ferruginyl methyl ether (10064-26-3,64199-80-0,64998-39-6,70051-26-2,94669-27-9,113059-71-5,113349-89-6) → (+/-)-ferruginol (514-62-5,10219-82-6,112744-09-9)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1002/bkcs.11538

upstream raw materials:

1,2,3,4,4a,9,10,10a-Octahydro-7-isopropenyl-6-methoxy-1,1,4a-trimethylphenanthrene

sugiol

(+/-)-ferruginol acetate

(+/-)-ferruginyl methyl ether

Downstream raw materials:

8β-Benzoyloxy-12-oxoabieta-9(11),13-dien

12-benzoyloxy-11-hydroxyabieta-8,11,13-triene

13α-Benzoyloxy-12-oxoabieta-8(14),9(11)-dien

13β-Benzoyloxy-12-oxoabieta-8(14),9(11)-dien

Refernces

• 1、 Zi, Jiachen,Peters, Reuben J.. "Characterization of CYP76AH4 clarifies phenolic diterpenoid biosynthesis in the Lamiaceae". . p. 7650 - 7652. Retrieved 2013.
• 2、 Wenkert,E. et al.. "-". . p. 2545 - 2549. Retrieved 1974.
• 3、 Yatagai, Mitsuyoshi,Takahashi, Toshii. "NEW DITERPENES FROM CHAMAECYPARIS PISIFERA". . p. 1149 - 1152. Retrieved 1980.
• 4、 -. "Synthesis method of aromatic avaietan diterpenoids". Paragraph 0094-0099. . Retrieved 2020/06/02.
• 5、 -. "(+/-)-ferruginol analogs and preparation method thereof, and applications of (+/-)-ferruginol analogs in preparation of antibacterial drugs". Paragraph 0403; 0404; 0407. . Retrieved 2018/11/03.