Shellolic acid

Base Information

• Chemical Name: Shellolic acid
• CAS No.: 4448-95-7
• Molecular Formula: C₁₅H₂₀O₆
• Molecular Weight: 296.32
• UNII: 82XGF31Q2Y
• Wikidata: Q27269360
• Mol file: 4448-95-7.mol

Synonyms:Shellolic acid;Shellolic acid [MI];UNII-82XGF31Q2Y;82XGF31Q2Y;4448-95-7;10beta,13-Dihydroxycedr-8-ene-12,15-dioic acid;1H-3a,7-Methanoazulene-3,6-dicarboxylic acid, 2,3,4,7,8,8a-hexahydro-4-hydroxy-8-(hydroxymethyl)-8-methyl-, (3R,3aS,4S,7R,8S,8aS)-;SCHEMBL310200;Q27269360;10.BETA.,13-DIHYDROXYCEDR-8-ENE-12,15-DIOIC ACID;(1S,2R,5S,6S,7R,10S)-10-hydroxy-6-(hydroxymethyl)-6-methyltricyclo[5.3.1.01,5]undec-8-ene-2,8-dicarboxylic acid

Chemical Property of Shellolic acid

Chemical Property:

• Vapor Pressure: 3.36E-15mmHg at 25°C
• Melting Point: 204-207°
• Boiling Point: 566.7°Cat760mmHg
• Flash Point: 310.6°C
• PSA: 115.06000
• Density: 1.48g/cm³
• LogP: 0.48760
• XLogP3: 0
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 296.12598835
• Heavy Atom Count: 21
• Complexity: 540

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC(C23CC1C(=CC3O)C(=O)O)C(=O)O)CO
• Isomeric SMILES: C[C@@]1([C@@H]2CC[C@H]([C@]23C[C@H]1C(=C[C@@H]3O)C(=O)O)C(=O)O)CO

Technology Process of Shellolic acid

There total 8 articles about Shellolic 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:

dimethyl 13-acetoxy-10α-hydroxycedr-8-ene-12,15-dioate (51979-03-4,64845-85-8,64845-88-1,64866-53-1) → 10-epi-shellolic acid (4448-95-7,6718-99-6,64845-86-9,64845-89-2,98306-85-5)

Guidance literature:

With sodium hydroxide; In water; at 30 ℃; for 15h;

Reference yield:

Dimethyl 13-acetoxy-10-oxocedr-8-ene-12,15-dioate (73272-50-1,73272-51-2) → 10-epi-shellolic acid (4448-95-7,6718-99-6,64845-86-9,64845-89-2,98306-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.015 g / NaBH₄ / methanol / Ambient temperature

2: NaOH / H₂O / 15 h / 30 °C

With sodium hydroxide; sodium tetrahydroborate; In methanol; water;

Reference yield:

→ (8aS)-4c-hydroxy-8t-methyl-8c-hydroxymethyl-(8arH)-1.2.4.7.8.8a-hexahydro-3H-3at.7t-methano-azulene-dicarboxylic acid-(3t.6) (4448-95-7,6718-99-6,64845-86-9,64845-89-2,98306-85-5)

Guidance literature:

Epischellolsaeure-dimethylester, wss.NaOH;

DOI:10.1016/S0040-4020(01)92705-X

upstream raw materials:

dimethyl 13-acetoxy-10α-hydroxycedr-8-ene-12,15-dioate

Dimethyl 13-acetoxy-10-oxocedr-8-ene-12,15-dioate

Refernces

• 1、 Subramanian, G. B. V.,Mahajan, Vijay K.,Ganesh, K. N.. "Oxygenated Cedrane Derivatives : Part IV - Sodium Borohydride Reductions of Some Oxo Derivatives of Cedranoid Terpenes". . p. 169 - 172. Retrieved 2007/10/02.