(9Z,12Z)-13-hydroxyoctadeca-9,12-dienoic acid

Base Information

• Chemical Name: (9Z,12Z)-13-hydroxyoctadeca-9,12-dienoic acid
• CAS No.: 67030-67-5
• Molecular Formula: C18H32O3
• Molecular Weight: 0

Synonyms:13-hydroxylinoleic acid

Chemical Property of (9Z,12Z)-13-hydroxyoctadeca-9,12-dienoic acid

Chemical Property:

• Vapor Pressure: 5.69E-09mmHg at 25°C
• Boiling Point: 424.1°C at 760 mmHg
• Flash Point: 224.5°C
• PSA: 57.53000
• Density: 0.972g/cm³
• LogP: 5.77020
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 296.23514488
• Heavy Atom Count: 21
• Complexity: 306

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=CCC=CCCCCCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C(=C/C/C=C\CCCCCCCC(=O)O)/O

Technology Process of (9Z,12Z)-13-hydroxyoctadeca-9,12-dienoic acid

There total 3 articles about (9Z,12Z)-13-hydroxyoctadeca-9,12-dienoic 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:

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → 13-hydroperoxylinoleic acid (34444-18-3) + 13-L-hydroxylinoleic acid (67030-67-5)

Guidance literature:

With t-butylnitrite; di-tert-butyl nitroxide; In ethanol; Product distribution; Ambient temperature; γ-irradiation;

DOI:10.1246/cl.1981.1599

Reference yield:

13-hydroperoxylinoleic acid (34444-18-3) → 13-L-hydroxylinoleic acid (67030-67-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; 1) 0 deg C, 20 min, 2) 25 deg C, 40 min.;

Reference yield:

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → 13-L-hydroxylinoleic acid (67030-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₄Cl/NH₄OH, borate / H₂O / 3 h / 25 °C / pH 9.0 , soybean lipoxygenase

2: NaBH₄ / methanol / 1) 0 deg C, 20 min, 2) 25 deg C, 40 min.

With ammonium hydroxide; sodium tetrahydroborate; boric acid; ammonium chloride; In methanol; water;

upstream raw materials:

linoleic acid

13-hydroperoxylinoleic acid

Refernces

Preparation of the enantiomers of hydroxy-C18 fatty acids and their anti-rice blast fungus activities

10.1016/S0957-4166(01)00486-4

The research aimed to investigate the relationship between the chirality of allylic alcohols and their anti-rice blast fungus activity. The study was motivated by the discovery of various oxygenated unsaturated fatty acids in rice plants, which play a crucial role in defending against rice blast fungus. Specifically, the allylic alcohols 16-hydroxy-γ-linolenic acid 1, 9-hydroxylinoleic acid 2, and 13-hydroxylinoleic acid 3 were of interest, as they accumulate in infected rice plants. The researchers synthesized both enantiomers of these allylic alcohols starting from the original fatty acids 4 and 5 and assessed their anti-fungal activities. The conclusion drawn from the study was that there was no noticeable correlation between the activity and chirality of the allylic alcohols. Chemicals used in the process included γ-linolenic and linoleic acids, hydroperoxy fatty acids, allylic alcohols, and epoxy fatty acids, among others. The synthesis involved various reagents and solvents such as n-BuLi, Pr2NH, CH2N2, (PhCO)2O/Et3N, and HPLC for purification and separation, as well as lipase PS, vinyl acetate, and thiacrown ether for the resolution of enantiomers.

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