Oleuropeic acid

Base Information

• Chemical Name: Oleuropeic acid
• CAS No.: 5027-76-9
• Molecular Formula: C10H16 O3
• Molecular Weight: 184.23
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID20198271
• Nikkaji Number: J14.268I
• Wikidata: Q72497808
• ChEMBL ID: CHEMBL4796626
• Mol file: 5027-76-9.mol

Synonyms:oleuropeic acid

Chemical Property of Oleuropeic acid

Chemical Property:

• Vapor Pressure: 2.75E-05mmHg at 25°C
• Boiling Point: 319.6°Cat760mmHg
• Flash Point: 161.3°C
• PSA: 57.53000
• Density: 1.171g/cm³
• LogP: 1.56840
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 241

Purity/Quality:

98%min ^*data from raw suppliers

Oleuropeicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C1CCC(=CC1)C(=O)O)O
• Isomeric SMILES: CC(C)([C@H]1CCC(=CC1)C(=O)O)O

Technology Process of Oleuropeic acid

There total 6 articles about Oleuropeic acid 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: 74.0%

(S)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxaldehyde (56197-78-5) → (S)-(-)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxylic acid (5027-76-9)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; In tert-butyl alcohol; cyclohexene; Ambient temperature;

Reference yield:

β-pinene oxide (56246-58-3) → (S)-(-)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxylic acid (5027-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / aq. carbonic acid / 2 h

2: 85 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1.) O deg C to room temperature, 2.) room temperature, 2 h

3: 74 percent / aq. sodium chlorite, potassium dihydrogenphosphate / 2-methyl-propan-2-ol; cyclohexene / Ambient temperature

With sodium chlorite; potassium dihydrogenphosphate; carbonic-acid; sodium acetate; pyridinium chlorochromate; In dichloromethane; tert-butyl alcohol; cyclohexene;

Reference yield:

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → (S)-(-)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxylic acid (5027-76-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / peracetic acid, sodium carbonate / CH₂Cl₂ / 2 h / 0 - 5 °C

2: 65 percent / aq. carbonic acid / 2 h

3: 85 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 1.) O deg C to room temperature, 2.) room temperature, 2 h

4: 74 percent / aq. sodium chlorite, potassium dihydrogenphosphate / 2-methyl-propan-2-ol; cyclohexene / Ambient temperature

With peracetic acid; sodium chlorite; potassium dihydrogenphosphate; carbonic-acid; sodium acetate; sodium carbonate; pyridinium chlorochromate; In dichloromethane; tert-butyl alcohol; cyclohexene;

upstream raw materials:

8-bromo-p-menth-1-en-7-oic acid

(S)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-carboxaldehyde

(4S)-4-(1-β-D-glucopyranosyloxy-1-methyl)ethyl-1-cyclohexene-1-carboxylic acid

β-pinene oxide

Refernces

• 1、 Pellegata, R.,Ventura, P.,Villa, M.,Palmisano, G.,Lesma, G.. "AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF OLEUROPEIC ACID. I". . p. 165 - 170. Retrieved 2007/10/02.