74784-20-6

Basic information

• Product Name: 13(S)-HOTRE
• Synonyms: 13S-HYDROXY-6Z,9Z,11E-OCTADECATRIENOIC ACID;13(S)-HYDROXY-9(Z),11(E),15(Z)-OCTADECATRIENOIC ACID;13(S)-HOT;13(S)-HOTE;13(S)-HOTRE;13(S)-HOTRE(GAMMA);13(S)-HYDROXYOCTADECA-6Z,9Z,11E-TRIENOIC ACID;13-hydroxy-6,9,11-octadecatrienoic acid
• CAS NO: 74784-20-6
• Molecular Formula: C18H30O3
• Molecular Weight: 294.43
• Mol File: 74784-20-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 436.5°C at 760 mmHg
• Flash Point: 231.9°C
• Appearance: /
• Density: 0.984g/cm³
• Vapor Pressure: 1.89E-09mmHg at 25°C
• Refractive Index: 1.504
• CAS DataBase Reference: 13(S)-HOTRE(CAS DataBase Reference)
• NIST Chemistry Reference: 13(S)-HOTRE(74784-20-6)
• EPA Substance Registry System: 13(S)-HOTRE(74784-20-6)

Safety Data

• Hazardous Substances Data: 74784-20-6(Hazardous Substances Data)

Usage

Classification

Chemical compound, oxylipin

Structure

13(S)-hydroperoxyoctadecatrienoic acid

Origin

Derived from fatty acids

Physiological role

Involved in various physiological processes

Anti-inflammatory properties

Known for its ability to reduce inflammation

Connection to jasmonic acid

Key player in the biosynthesis of this signaling molecule

Defense responses

Involved in plant defense responses

Anti-cancer properties

Has been found to possess anti-cancer properties

Therapeutic potential

Potential candidate for the development of novel therapeutic agents

Importance in research

Target for further research in pharmacology and medicine due to its role in mediating inflammation and cancer.

InChI:InChI=1/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h4,6-7,9,12,15,17,19H,2-3,5,8,10-11,13-14,16H2,1H3,(H,20,21)/b6-4-,9-7-,15-12+/t17-/m0/s1

Upstream product

• 28659-22-5 6-(tetrahydro-2H-pyranyloxy)hexan-1-ol 
• 506-26-3 all-cis-6,9,12-octadecatrienoic acid 
• 600180-01-6 13-benzyloxy-(6Z,9Z,11E,13S)-6,9,11-octadecatriene-1-ol 
• 600179-98-4 1-[7-benzyloxy-(3Z,5E,7S)-3,5-dodecadienyloxymethyl]-4-methoxybenzene 
• 600179-97-3 12-(4-methoxybenzyloxy)-1-pentyl (1S,2E,4Z)-2,4-heptadienyl alcohol 
• 600180-00-5 1-[7-iodo-1-pentyl-(1S,2E,4Z)-2,4-heptadienyloxymethyl]benzene 
• 600179-99-5 7-benzyloxy-(3Z,5E,7S)-3,5-dodecadiene-1-ol 
• 600179-95-1 7-benzyloxy-(3Z,5E,7S)-3,5-dodecadien-1-al 
• 392333-43-6 7-hydroxy-(3Z,5E,7S)-3,5-dodecadienyl 5-hydroxypentanoate 
• 392333-39-0 (3Z,6Z)-3,6-dodecadienyl 5-hydroxypentanoate 
• 124099-42-9 (3Z,5E,7S)-3,5-dodecadiene-1,7-diol 
• 50889-29-7 (5-carboxypentyl)triphenylphosphonium bromide 
• 33803-62-2 6-(tetrahydropyrane-2-yloxy)hexan-1-al 
• 4224-70-8 6-bromohexanoic acid 

Relevant articles and documents

Oxidation of Octadecatrienoic Acids in the Red Alga Lithothamnion corallioides: Structural and Stereochemical Studies of Conjugated Tetraene Fatty Acids and Bis Allylic Hydroxy Acids

Enzymatic oxidation of (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid (γ-linolenic acid; 1a) in a preparation of the red alga Lithothamnion corallioides Crouan led to the formation of (6Z,8E,10E,12Z)-octadeca-6,8,10,12-tetraenoic acid 2a and (11R,6Z,9Z,12Z)-hydroxyoctadeca-6,9,12-trienoic acid 3a as the main products. (9Z,12Z,15Z)-Octadeca-(9,12,15)-trienoic acid (α-linolenic acid; 4a) was oxidized in an analogous way to yield (9Z,11E,13E,15Z)-octadeca-9,11,13,15-tetraenoic acid (α-parinaric acid; 5a), (11S,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid 6a, and (14R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid 7a.Isotope studies demonstrated that enzymatic conversion of the acid 1a into the tetraene 2a was accompanied by stereospecific eliminations of the pro-S and pro-R hydrogens from C-8 and C-11, respectively.The bis-allylic hydroxy acid 3a was formed from acid 1a by a reaction involving stereospecific elimination of the pro-S hydrogen from C-11 and incorporation of 1 atom of oxygen from water in the C-11 hydroxy group.Although the bis allylic hydroxy esters 3b, 6b, and 7b were chemically convertible into conjugated tetraenes by rapid acid-catalysed dehydration, enzymatic formation of conjugated tetraenes and hydroxy acids in Lithothamnion occured by independent pathways.

Asymmetric synthesis of unnatural (Z,Z,E)-octadecatrienoid and eicosatrienoid by lipoxygenase-catalyzed oxygenation

The asymmetric synthesis of unnatural 13-hydroxy-(6Z,9Z,11E,13S)-octadecatrienoid and 15-hydroxy-(8Z,11Z,13E,15S)-eicosatrienoid is described using a biomimetic oxidation route. The main highlights of this synthesis are the asymmetric hydroxylation of the substrate with soybean lipoxygenase and cis selective Wittig olefination.