(3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid

Base Information

• Chemical Name: (3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid
• CAS No.: 31653-05-1
• Molecular Formula: C₂₀H₄₀O₂
• Molecular Weight: 312.536
• UNII: DNI0G88EKC
• DSSTox Substance ID: DTXSID801227433
• Nikkaji Number: J1.164.329I
• Wikidata: Q27896750
• Metabolomics Workbench ID: 333
• Mol file: 31653-05-1.mol

Synonyms:(3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid;Phytanic acid, L,d,D-;DNI0G88EKC;31653-05-1;3L,7D,11D-Phytanic acid;Phytanic acid, (3S,7R,11R)-;UNII-DNI0G88EKC;Phytanic acid, (3S,7R,11R)-(-)-;3S,7R,11R,15-Tetramethylhexadecanoic acid;Hexadecanoic acid, 3,7,11,15-tetramethyl-, (3S,7R,11R)-;3L,7D,11D-Phytanate;SCHEMBL3819827;(3S,7R,11R)-phytanic acid;CHEBI:179700;DTXSID801227433;3S,7R,11R,15-tetramethyl-hexadecanoic acid;Q27896750;3,7,11,15-tetramethyl-[3S-(3R*,7S*,11S*)]-Hexadecanoate;3,7,11,15-tetramethyl-[3S-(3R*,7S*,11S*)]-Hexadecanoic acid

Chemical Property of (3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid

Chemical Property:

• Boiling Point: 422.3°Cat760mmHg
• Flash Point: 179.7°C
• PSA: 37.30000
• Density: 0.88g/cm³
• LogP: 6.53630
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 312.302830514
• Heavy Atom Count: 22
• Complexity: 273

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid

There total 9 articles about (3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic 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:

(Z)-phytol (5492-30-8,844467-91-0) → (3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid (31653-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II) / methanol / 24 h / 77572.2 Torr

2: CrO₃ / acetone; aq. acetic acid / 1 h / Ambient temperature

With chromium(VI) oxide; hydrogen; <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>diacetatoruthenium(II); In methanol; acetic acid; acetone;

DOI:10.1021/jo00071a049

Reference yield:

C32H50N2O2 → (3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid (31653-05-1)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 24h;

DOI:10.1071/CH99001

Reference yield:

(3RS,7R,11R)-3,7,11,15-tetramethylhexadecan-1-ol (189302-44-1) → (3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoic acid (31653-05-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / CrO₃ / H₂O; acetone; acetic acid / 1 h / 20 °C

2: oxalyl chloride / DMF / diethyl ether / 1 h / 20 °C

3: NEt₃ / CH₂Cl₂ / 2 h / 20 °C

4: NaNO₂ / acetic acid; acetic anhydride / 4 h / 20 °C

5: LiOH; 30 percent H₂O₂ / tetrahydrofuran; H₂O / 24 h / 0 - 20 °C

With chromium(VI) oxide; lithium hydroxide; oxalyl dichloride; dihydrogen peroxide; triethylamine; sodium nitrite; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic anhydride; acetic acid; acetone; 1: Oxidation / 2: Chlorination / 3: Substitution / 4: Nitrosation / 5: Hydrolysis;

DOI:10.1071/CH99001

upstream raw materials:

(3S,7R,11R)-3,7,11,15-Tetramethylhexadecan-1-ol

(3RS,7R,11R)-3,7,11,15-tetramethylhexadecan-1-ol

(3S,7R,11R)-N-<(1R)-1-Naphthylethyl>-3,7,11,15-tetramethylhexadecanamide

(3RS,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid