Zeylenol

Base Information

• Chemical Name: Zeylenol
• CAS No.: 78804-17-8
• Molecular Formula: C21H20 O7
• Molecular Weight: 384.386
• UNII: UVM7L54PBC
• DSSTox Substance ID: DTXSID70451085
• Nikkaji Number: J1.540.119B
• Wikidata: Q72516828
• ChEMBL ID: CHEMBL4469789
• Mol file: 78804-17-8.mol

Synonyms:zeylenol

Chemical Property of Zeylenol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 131-132oC
• Boiling Point: 549.615oC at 760 mmHg
• Flash Point: 192.395oC
• PSA: 113.29000
• Density: 1.395g/cm3
• LogP: 1.09170
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 384.12090297
• Heavy Atom Count: 28
• Complexity: 577

Purity/Quality:

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

((1R,2S,5R,6S)-5-(Benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methylBenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2(C(C=CC(C2O)OC(=O)C3=CC=CC=C3)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@]2([C@H](C=C[C@H]([C@@H]2O)OC(=O)C3=CC=CC=C3)O)O
• Uses: Sanjiaozi, also known as Dahua Ziyupan, belongs to the genus Ziyupan of the Ansopaceae family. It is mainly distributed in southern Guangdong and its islands in my country. It grows in low-altitude shrubs or hills and mountain forests, in South Asia, Southeast Asia, etc. It is also distributed in tropical and subtropical regions. Sanchoenol is an organic alcohol with anti-inflammatory and anti-tumor biological activities, which can be used in scientific research experiments.

Technology Process of Zeylenol

There total 34 articles about Zeylenol 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: 72.0%

((3aR,4S,7R,7aS)-7-(benzoyloxy)-4-hydroxy-2,2-dimethyl-7,7a-dihydrobenzo[d][1,3]dioxol-3a(4H)-yl)methyl benzoate → ((1R,2S,5R,6S)-5-(benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate (78804-17-8)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 5h;

DOI:10.1016/j.tetlet.2017.02.003

Reference yield: 50.0%

(+)-Pipoxide (29399-87-9) → ((1R,2S,5R,6S)-5-(benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate (78804-17-8) + (1R,4S,5S,6S)-5,6-dihydroxy-5-(hydroxymethyl)cyclohex-2-ene-1,4-diyl dibenzoate (122585-45-9)

Guidance literature:

In dichloromethane; for 2h; -20 deg C to rt;

DOI:10.1016/S0040-4039(00)85583-5

Reference yield: 45.0%

C30H38O7Si (1379659-90-1) → <(+)-zeylenol> (78804-17-8,92620-04-7,113532-12-0) + (1R,2S,3R,4S)-2-hydroxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,4-dibenzoate

Guidance literature:

With methanol; iodine; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201104035

upstream raw materials:

C₃₀H₄₄O₇Si₃

(+)-Pipoxide

benzoyl chloride

(+)-(1R,4S,4aR,5S,8aS)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one

Downstream raw materials:

(+)-(1R,2S,3R,4S)-2-benzoyloxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,2,3-triacetate 4-benzoate

(-)-Uvarigranol G

2-O-acetylzeylenone

(+)-Pipoxide

Refernces

• 1、 Palframan, Matthew J.,Kociok-Koehn, Gabriele,Lewis, Simon E.. "Photooxygenation of a microbial arene oxidation product and regioselective Kornblum-DeLamare rearrangement: Total synthesis of zeylenols and zeylenones". experimental part. p. 4766 - 4774. Retrieved 2012/05/04.
• 2、 Pancharoen, Orasa,Tuntiwachwuttikul, Pittaya,Taylor, Walter C.. "CYCLOHEXANE OXIDE DERIVATIVES FROM KAEMPFERIA ANGUSTIFOLIA AND KAEMPFERIA SPECIES". . p. 1143 - 1148. Retrieved 2007/10/02.