Calendic acid

Base Information

• Chemical Name: Calendic acid
• CAS No.: 5204-87-5
• Molecular Formula: C₁₈H₃₀O₂
• Molecular Weight: 278.435
• Hs Code.: 2916190090
• UNII: DK8G4N35L5
• DSSTox Substance ID: DTXSID80897455
• Wikipedia: Calendic_acid
• Wikidata: Q2823246
• Metabolomics Workbench ID: 576
• Mol file: 5204-87-5.mol

Synonyms:calendic acid

Chemical Property of Calendic acid

Chemical Property:

• Vapor Pressure: 2.36E-08mmHg at 25°C
• Boiling Point: 423.4°Cat760mmHg
• Flash Point: 320.1°C
• PSA: 37.30000
• Density: 0.924g/cm³
• LogP: 5.66050
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 278.224580195
• Heavy Atom Count: 20
• Complexity: 301

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC=CC=CCCCCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C\C=C\C=C\CCCCCCC(=O)O

Technology Process of Calendic acid

There total 26 articles about Calendic 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:

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran (53963-10-3) → Octadeca-8t,10t,12c-triensaeure (5204-87-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-butyl-lithium / 1.) TFH/HMPA/hexane, 0 deg C; 2.) THF/HMPA/hexane, 30 min, r.t.

2: deuterium / chlorotris(triphenylphosphine)rhodium / benzene-d6 / 12 h

3: 71 percent / PPTS / ethanol / 3 h / 35 °C

4: 68 percent / PCC / CH₂Cl₂ / 2 h / 20 °C

5: 46 percent / deuterium oxide / pyridine / 7 h / 90 - 95 °C / procedure repeated twice more

6: 1.) t-butyl-lithium / 1.) hexane, 0 deg C, 5 min; 2.) THF, 0 deg C -> r.t., 2 h

7: potassium hydroxide / aq. ethanol

8: marigold (Calendula officinalis) seed homogenate

With potassium hydroxide; n-butyllithium; water-d2; tert.-butyl lithium; pyridinium p-toluenesulfonate; deuterium; pyridinium chlorochromate; Wilkinson's catalyst; In pyridine; ethanol; dichloromethane; benzene-d6;

Reference yield:

9-(tetrahydropyran-2-yloxy)non-2-yne (85484-80-6) → Octadeca-8t,10t,12c-triensaeure (5204-87-5)

Guidance literature:

Multi-step reaction with 7 steps

1: deuterium / chlorotris(triphenylphosphine)rhodium / benzene-d6 / 12 h

2: 71 percent / PPTS / ethanol / 3 h / 35 °C

3: 68 percent / PCC / CH₂Cl₂ / 2 h / 20 °C

4: 46 percent / deuterium oxide / pyridine / 7 h / 90 - 95 °C / procedure repeated twice more

5: 1.) t-butyl-lithium / 1.) hexane, 0 deg C, 5 min; 2.) THF, 0 deg C -> r.t., 2 h

6: potassium hydroxide / aq. ethanol

7: marigold (Calendula officinalis) seed homogenate

With potassium hydroxide; water-d2; tert.-butyl lithium; pyridinium p-toluenesulfonate; deuterium; pyridinium chlorochromate; Wilkinson's catalyst; In pyridine; ethanol; dichloromethane; benzene-d6;

Reference yield:

9-oxo-(10E,12Z)-octadecadien-1-oic acid methyl ester (64265-96-9) → Octadeca-8t,10t,12c-triensaeure (5204-87-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 23 mg / sodium borotritide, sodium borohydride / methanol / 0.08 h / 0 °C

2: 20 mg / KOH / ethanol; H₂O / 1 h / Heating

3: marigold (Calendula officinalis) seed homogenate

With potassium hydroxide; sodium tetrahydroborate; sodium boron [ 3H]hydride; In methanol; ethanol; water;

upstream raw materials:

8,10-trans,12-cis-octadecatrienoic acid methyl ester

<8,8,11,11,16,16,17,17-2H8>octadec-(9Z)-enoic acid

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

Methyl oleate

Downstream raw materials:

t8,t10,t12-linolenic acid

Refernces