Tuberculostearic acid

Base Information

• Chemical Name: Tuberculostearic acid
• CAS No.: 542-47-2
• Molecular Formula: C19H38O2
• Molecular Weight: 298.51
• NSC Number: 625426
• UNII: C2LR962W58
• DSSTox Substance ID: DTXSID50862155
• Nikkaji Number: J108.049K
• Wikipedia: Tuberculostearic_acid
• Wikidata: Q2823320
• Metabolomics Workbench ID: 74882
• Mol file: 542-47-2.mol

Synonyms:10-methyloctadecanoic acid;10-methylstearic acid;tuberculostearic acid

Chemical Property of Tuberculostearic acid

Chemical Property:

• Vapor Pressure: 4.64E-08mmHg at 25°C
• Melting Point: 20-21 °C
• Refractive Index: 1.4466 (estimate)
• Boiling Point: 415.3°Cat760mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 234.5°C
• PSA: 37.30000
• Density: 0.885g/cm³
• LogP: 6.57850
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 298.287180451
• Heavy Atom Count: 21
• Complexity: 226

Purity/Quality:

99%, ^*data from raw suppliers

TuberculostearicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCC(C)CCCCCCCCC(=O)O
• Uses: Tuberculostearic Acid is a saturated fatty acid produced by Actinomycetales bacteria.

Technology Process of Tuberculostearic acid

There total 30 articles about Tuberculostearic 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: 44.0%

(R,S)-10-methyloctadecanol (2490-04-2) → 10-Methyl-octadecanoic acid (542-47-2,80508-15-2)

Guidance literature:

With dipyridinium dichromate; 4 A molecular sieve; In N,N-dimethyl-formamide; for 120h; Ambient temperature;

DOI:10.1016/0009-3084(94)90067-1

Reference yield:

1,6-hexanediol (629-11-8) → 10-Methyl-octadecanoic acid (542-47-2,80508-15-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 48 percent / iron (III) sulphate on silica gel / hexane / 1.42 h / 45 °C

2: 84 percent / pyridine / CH₂Cl₂ / 16 h / Ambient temperature

3: 46 percent / I₂, 1,2-bis(diphenylphosphino)ethane / CH₂Cl₂ / 4 h / Ambient temperature

4: 34 percent / dimethylsulfoxide / 2 h / Ambient temperature

5: 79 percent / trifluoroacetic acid, H₂O / CH₂Cl₂

6: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, 0 deg C, 1.5 h

7: 88 percent / H₂ / 10percent Pd/C / diethyl ether / 16 h

8: 44 percent / molecular sieves 4 A, pyridinum dichromate / dimethylformamide / 120 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; n-butyllithium; 4 A molecular sieve; water; hydrogen; iodine; trifluoroacetic acid; 1,2-bis-(diphenylphosphino)ethane; iron(III) sulfate; palladium on activated charcoal; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0009-3084(94)90067-1

Reference yield:

2-methyldecan-1-ol (18675-24-6) → 10-Methyl-octadecanoic acid (542-47-2,80508-15-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / I₂, chlorodiphenylphosphine, imidazole / toluene / 3 h / 70 °C

2: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -78 deg C to RT, 1 h, 2.) THF, hexane, form -78 deg C to RT, 4 h

3: 68 percent / methanolic para-toluenesulfonic acid / toluene / 144 h

4: 88 percent / H₂ / 10percent Pd/C / diethyl ether / 16 h

5: 44 percent / molecular sieves 4 A, pyridinum dichromate / dimethylformamide / 120 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; n-butyllithium; 4 A molecular sieve; hydrogen; iodine; toluene-4-sulfonic acid; chloro-diphenylphosphine; palladium on activated charcoal; In diethyl ether; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0009-3084(94)90067-1

upstream raw materials:

3-methylundecanoic acid

azelaic monomethyl ester

(R)-10-methyloctadecanoic acid

(S)-10-methyloctadecanoic acid

Downstream raw materials:

(+/-)-10-methyl-octadecanoic acid amide

ethyl (R,S)-10-methyloctadecanoate

methyl (R,S)-10-methyloctadecanoate

Refernces

• 1、 Wallace, Paul A.,Minnikin, David E.,McCrudden, Katharine,Pizzarello, Andrea. "Synthesis of (R,S)-10-methyloctadecanoic acid (tuberculostearic acid) and key chiral 2-methyl branched intermediates". . p. 145 - 162. Retrieved 2007/10/02.