Spathulenol

Base Information

• Chemical Name: Spathulenol
• CAS No.: 6750-60-3
• Molecular Formula: C15H24O
• Molecular Weight: 220.355
• UNII: 7XV9L96SJJ
• Nikkaji Number: J16.275B
• Wikipedia: Spathulenol
• Wikidata: Q1376658
• ChEMBL ID: CHEMBL518542
• Mol file: 6750-60-3.mol

Synonyms:spathulenol

Chemical Property of Spathulenol

Chemical Property:

• Vapor Pressure: 0.000141mmHg at 25°C
• Boiling Point: 297°C at 760 mmHg
• PKA: 15.10±0.40(Predicted)
• Flash Point: 123.9°C
• PSA: 20.23000
• Density: 1.02g/cm³
• LogP: 3.38580
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 220.182715385
• Heavy Atom Count: 16
• Complexity: 343

Purity/Quality:

99%, ^*data from raw suppliers

Spathulenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2C1C3C(CCC3(C)O)C(=C)CC2)C
• Isomeric SMILES: C[C@@]1(CC[C@@H]2[C@@H]1[C@H]3[C@H](C3(C)C)CCC2=C)O
• Description: Spathulenol?is a tricyclic?sesquiterpene?alcohol which has a basic skeleton similar to the?azulenes,it occurs in?oregano?among other plants.
• Uses: Eucalyptol is an organic alcohol compound, mainly used for content determination and experimental research, not for other purposes.

Technology Process of Spathulenol

There total 15 articles about Spathulenol 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: 79.0%

(+)-11β-hydroxy-apoaromadendrone (99147-42-9) + Methylenetriphenylphosphorane (19493-09-5) → spathulenol (6750-60-3)

Guidance literature:

DOI:10.1016/S0040-4039(00)94792-0

Reference yield: 57.0%

(+)-bicyclogermacrene (41437-00-7,67650-49-1,67650-90-2,79951-53-4,100762-45-6,100762-46-7,100762-48-9,100762-49-0,133005-43-3,24703-35-3) → spathulenol (6750-60-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform-d1; chloroform; at 25 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/chem.201403082

Reference yield:

(-)-apoaromadendrone (6790-66-5,14682-45-2,14917-87-4,95977-69-8,97275-30-4,97950-12-4,99147-41-8) → spathulenol (6750-60-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / NaIO₄, RuO₂*xH₂O / CCl₄; acetonitrile; H₂O / 48 h / 50 °C

2: 1) Mg, I₂, 2) conc. H₂SO₄ / 1) ether, reflux, 2) THF, rt, 2 h

With ruthenium(IV) oxide; sodium periodate; sulfuric acid; iodine; magnesium; In tetrachloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)88765-2

upstream raw materials:

(+)-11β-hydroxy-apoaromadendrone

Methylenetriphenylphosphorane

Chloromethyltrimethylsilane

(1S,3aR,8aS)-3a-methyl-7-methylidene-1-propan-2-yl-2,3,5,6,8,8a-hexahydro-1H-azulen-4-one

Downstream raw materials:

4β,10β-aromadendranediol

4β,10α-aromadendranediol

β-Spathulen

Refernces

• 1、 Gijsen, Harrie J. M.,Wijnberg, Joannes B. P. A.,Stork, Gerrit A.,De Groot, Aede,De Waard, Maarten A.,Van Nistelrooy, Johannes G. M.. "The synthesis of mono- and dihydroxy aromadendrane sesquiterpenes, starting from natural (+)-aromadendrene-III". . p. 2465 - 2476. Retrieved 2007/10/02.
• 2、 Maurer, Bruno,Hauser, Arnold. "New Sesquiterpenoids from Clary Sage Oil (Salvia sclarea L.)". . p. 2223 - 2235. Retrieved 2007/10/02.