Elenolic acid

Base Information

• Chemical Name: Elenolic acid
• CAS No.: 34422-12-3
• Deprecated CAS: 24582-90-9,51050-95-4
• Molecular Formula: C11H14 O6
• Molecular Weight: 242.229
• UNII: 5C9M8PFI8E
• DSSTox Substance ID: DTXSID30188002
• Nikkaji Number: J732.186D
• Wikipedia: Elenolic_acid
• Wikidata: Q2635498
• Metabolomics Workbench ID: 48440
• Mol file: 34422-12-3.mol

Synonyms:calcium elenolate;elenolic acid;elenolic acid Ca salt, (2S-(2alpha,3alpha,4beta))-isomer;elenolic acid, calcium (2:1) salt, (2S-(2alpha,3alpha,4beta))-isomer

Chemical Property of Elenolic acid

Chemical Property:

• Vapor Pressure: 7.87E-08mmHg at 25°C
• Boiling Point: 408.9°Cat760mmHg
• PKA: 4.40±0.10(Predicted)
• Flash Point: 158.2°C
• PSA: 89.90000
• Density: 1.308g/cm³
• LogP: 0.36800
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 242.07903816
• Heavy Atom Count: 17
• Complexity: 359

Purity/Quality:

98%Min ^*data from raw suppliers

ElenolicAcid(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(=CO1)C(=O)OC)CC(=O)O)C=O
• Isomeric SMILES: C[C@H]1[C@H]([C@@H](C(=CO1)C(=O)OC)CC(=O)O)C=O
• Uses: Elenolic Acid is an antiviral agent that inhibits reverse transcriptases, inhibited the growth of chicken embryo fibroblast cells as well as Escherichia coli and Bacillus subtilis strains.

Technology Process of Elenolic acid

There total 17 articles about Elenolic 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:

(4S,5S,6S)-4-Carboxymethyl-6-methyl-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (97387-88-7) → (-)-Elenolic acid (34422-12-3,24582-90-9)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; water; at 0 ℃; Yield given;

DOI:10.1016/S0040-4039(00)61950-0

Reference yield:

(E)-(4S) ethyl 4-(2-tetrahydropyranyloxy)pent-2-enoate (97387-90-1) → (-)-Elenolic acid (34422-12-3,24582-90-9)

Guidance literature:

Multi-step reaction with 14 steps

1: Aluminium hydride / diethyl ether / -60 °C

2: t-BuCOOH / 140 °C

3: PPTS / ethanol / Heating

4: LDA / tetrahydrofuran / -78 °C

5: 1.) DIBAL / 1.) CH₂Cl₂, -78 deg C 2.) glyme, room temp.

6: imidazole / dimethylformamide / Ambient temperature

7: pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

8: p-TsOH / methanol / Heating

9: 72 h / 170 °C

10: 1.) 1N HCl 2.) 5percent H₂SO₄ / 1.) Et₂O, room temp. 2.) reflux

11: osmium tetroxide / pyridine / 0 °C / epimers ratio 8:7

12: lead tetracetate / tetrahydrofuran / 0 °C

13: CrO₃, H₂SO₄ / acetone / 0 °C

14: OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 0 °C

With 1H-imidazole; chromium(VI) oxide; aluminium hydride; lead(IV) acetate; hydrogenchloride; sodium periodate; osmium(VIII) oxide; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; Trimethylacetic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)61950-0

Reference yield:

(4S,E)-4-((tetrahydro-2H-pyran-2-yl)oxy)pent-2-en-1-ol (97415-38-8) → (-)-Elenolic acid (34422-12-3,24582-90-9)

Guidance literature:

Multi-step reaction with 13 steps

1: t-BuCOOH / 140 °C

2: PPTS / ethanol / Heating

3: LDA / tetrahydrofuran / -78 °C

4: 1.) DIBAL / 1.) CH₂Cl₂, -78 deg C 2.) glyme, room temp.

5: imidazole / dimethylformamide / Ambient temperature

6: pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

7: p-TsOH / methanol / Heating

8: 72 h / 170 °C

9: 1.) 1N HCl 2.) 5percent H₂SO₄ / 1.) Et₂O, room temp. 2.) reflux

10: osmium tetroxide / pyridine / 0 °C / epimers ratio 8:7

11: lead tetracetate / tetrahydrofuran / 0 °C

12: CrO₃, H₂SO₄ / acetone / 0 °C

13: OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 0 °C

With 1H-imidazole; chromium(VI) oxide; lead(IV) acetate; hydrogenchloride; sodium periodate; osmium(VIII) oxide; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; Trimethylacetic acid; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)61950-0

upstream raw materials:

(S)-4-(1-formyl-trans-propenyl)-6-oxo-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

(4S,5S,6S)-4-Carboxymethyl-6-methyl-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

oleuropeine

(E)-(4S) ethyl 4-(2-tetrahydropyranyloxy)pent-2-enoate

Downstream raw materials:

ajmalicine

Refernces

• 1、 Hatakeyama,Saijo,Takano. "Enantioselective synthesis of (-)-elenolic acid and (-)-ajmalicine". . p. 865 - 868. Retrieved 2007/10/02.