(9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid

Base Information

• Chemical Name: (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid
• CAS No.: 89886-42-0
• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 294.434
• Hs Code.: 2918199090
• Metabolomics Workbench ID: 45191
• Nikkaji Number: J532.647H,J2.891.041J
• Wikidata: Q27161577
• Mol file: 89886-42-0.mol

Synonyms:(10E,12Z,15Z)-9-OH-10,12,15-ODTA;9-hydroxy-10,12,15-octadecatrienoic acid;9-OH-10,12,15-ODTA

Chemical Property of (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid

Chemical Property:

• Vapor Pressure: 3.74E-09mmHg at 25°C
• Boiling Point: 428.9 ºCat 760 mmHg
• Flash Point: 227.3 ºC
• PSA: 57.53000
• Density: 0.984 g/cm³
• LogP: 4.63130
• Storage Temp.: −20°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 294.21949481
• Heavy Atom Count: 21
• Complexity: 329

Purity/Quality:

99% ^*data from raw suppliers

9(S)-HOTrE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CC=CC(CCCCCCCC(=O)O)O
• Isomeric SMILES: CC/C=C/C/C=C/C=C/C(CCCCCCCC(=O)O)O
• Uses: 9(S)-HOTrE is a monohydroxy polyunsaturated fatty acid produced by the action of 5-lipoxygenase on α-linolenic acid. 9(S)-HOTrE is predominantly localized in cellular ester lipids of Glechoma hederacea leaves and is partially released during artificial dehydration. The biological role of 9(S)-HOTrE in G. hederacea leaves is still undetermined, but it may play a role in natural senescence. 9(S)-HOTrE is an inhibitor of spore germination and germ tube elongation of rice blast fungus with ED50 values of 45 and 30 ppm, respectively.[Cayman Chemical]

Technology Process of (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic acid

There total 2 articles about (9S,10E,12Z,15Z)-9-Hydroxy-10,12,15-octadecatrienoic 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: 53.0%

(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid (111004-08-1) → (9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid (89886-42-0)

Guidance literature:

With phosphorous acid trimethyl ester; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(02)00231-4

Reference yield:

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0) → (9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid (89886-42-0)

Guidance literature:

With sodium tetrahydroborate; tomato lipoxygenase; Multistep reaction;

DOI:10.1039/P19930003065

Reference yield: 69.0%

(9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid (89886-42-0) → 9-oxo-(10E,12Z,15Z)-octadecatrienoic acid (125559-74-2)

Guidance literature:

With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)00231-4

upstream raw materials:

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid

Downstream raw materials:

9-oxo-(10E,12Z,15Z)-octadecatrienoic acid

Refernces

• 1、 Hamberg, Mats. "Oxidation of Octadecatrienoic Acids in the Red Alga Lithothamnion corallioides: Structural and Stereochemical Studies of Conjugated Tetraene Fatty Acids and Bis Allylic Hydroxy Acids". . p. 3065 - 3072. Retrieved 2007/10/02.